2023 Thailand – Taiwan Bilateral Symposium at Classic Kameo Hotel & Serviced Apartment Ayutthaya, Thailand July 23 - 26, 2023 Organized by Program Management Unit for Human Resources & Institutional Development, Research and Innovation (PMU-B) A research network that aims to promote academic excellence in the development of bioresources in Thailand through partnerships of high-caliber scientists (BioMeta)
TABLE OF CONTENTS Pages PROGRAM: 2023 Thailand – Taiwan Bilateral Symposium 1 ABSTRACTS: Invited Lectures 4 Poster Presentations 19 LIST OF PARTICIPANTS 37
Sunday, July 23, 2023 Arrival in Ayutthaya and Check-in at the Hotel Registration and Poster Set-up Free Time Monday, July 24, 2023 Opening Ceremony Invited Lectures Lunch Poster Session Invited Lectures Friendship Dinner Tuesday, July 25, 2023 Paralled Group Discussion and Summary of the Key Points Lunch Excursion Farewell Dinner Wednesday, July 26, 2023 Departure from Ayutthaya 13.00 - 16.30 17.00 11.00 12.00 - 13.00 2023 Thailand - Taiwan Bilateral Symposium July 23 - 26, 2023, Classic Kameo Hotel & Serviced Apartment, Ayutthaya, THAILAND PROGRAM HIGHLIGHTS 17.00 - 18.00 08.30 - 08.50 08.50 - 12.00 12.00 - 13.00 13.00 - 14.00 14.00 - 17.40 18.30 09.00 - 12.00 1
Chairpersons: Assoc. Prof. Dr.Pasit Pakawatpanurut and Asst. Prof. Dr.Chutima Jiarpinitnun IL.NS-01 IL.OB-01 IL.NS-02 IL.OB-02 IL.OB-03 IL.OB-04 IL.OB-05 Chairpersons: Assoc. Prof. Dr.Pasit Pakawatpanurut and Asst. Prof. Dr.Chutima Jiarpinitnun IL.OB-06 11.10 - 11.35 Computational study of nanostructure materials for net zero climateresilient future: energy applications and carbon utilization by Prof. Dr.Siriporn Jungsuttiwong 11.35 - 12.00 Semiconducting polymer photocatalysts for solar-driven hydrogen evolution by Assoc. Prof. Dr.Ho-Hsiu Chou 12.00 - 13.00 Lunch 13.00 - 14.00 Poster Session 14.00 - 14.25 From covalently linked peptide-membrane interactions to triggerresponsive peptidyl liposomes by Dr.Hsien-Ming Lee 10.05 - 10.20 Coffee Break 10.20 - 10.45 Development of solid-state Li-ion and metal-air batteries by Prof. Dr.Ru-Shi Liu 10.45 - 11.10 Can electronic structure provide understanding on Carbon-Carbon coupling reaction 2*CO→*OCCO on B-doped Graphyne? by Dr.Kaito Takahashi 09.40 - 10.05 Translational research and spin-off: novel kinase inhibitors from bench to clinic by Prof. Dr.Hsing-Pang Hsieh 2023 Thailand - Taiwan Bilateral Symposium July 23 - 26, 2023, Classic Kameo Hotel & Serviced Apartment, Ayutthaya, THAILAND Monday, July 24, 2023 YODIA 08.50 - 09.15 Discovery of potential neuroprotective compounds against chemotherapyinduced peripheral neuropathy by Prof. Dr.Jang-Yang Chang 09.15 - 09.40 Advances in MS-based metabolomics for natural product frontier research by Assoc. Prof. Dr.Sakda Khoomrung 2
IL.NS-03 IL.NS-04 IL.NS-05 IL.NS-06 IL.NS-07 IL.OB-07 IL.OB-08 Paralled Group Discussion and Summary of the Key Points Lunch Paralled Group Discussion and Summary of the Key Points Lunch Tuesday, July 25, 2023 YODIA 2 / NSF 09.00 - 12.00 12.00 - 13.00 17.15 - 17.40 X-ray absorption spectroscopy: the state of the art synchrotron-based characterization for energy materials by Dr.Pinit Kidkhunthod Tuesday, July 25, 2023 YODIA 1 / OBF 09.00 - 12.00 12.00 - 13.00 16.00 - 16.25 Enantioselective synthesis of 1-aryl tetrahydroisoquinolines by the rhodiumcatalyzed reaction of 3,4-dihydroisoquinolinium tetraarylborates by Prof. Dr.Hsyueh-Liang Wu 16.25 - 16.50 Nitrogen heterocycles: synthesis through cascade cyclization and their potentials as drug prototypes by Prof. Dr.Chutima Kuhakarn 16.50 - 17.15 Oxidation reactions of HMF and furfural by Assoc. Prof. Dr.Ekasith Somsook 14.50 - 15.15 Riboflavin functionalized nanoparticles and its potential use for breast cancer treatment by Assoc. Prof. Dr.Kanlaya Katewongsa 15.15 - 15.40 Anti-cancer drug discovery from natural bioactive compounds and their underlying mechanisms by Assoc. Prof. Dr.Arthit Chairoungdua 15.40 - 16.00 Coffee Break 14.25 - 14.50 CRISPR Cas9-mediated ablation of pyruvate carboxylase gene in colon cancer cells inhibits growth and migration, induces apoptosis and increases sensitivity to 5-fluorouracil and glutaminase inhibitor by Prof. Dr.Sarawut Jitrapakdee 3
IL.NS-01 PHOTO Height 2.5 cm Width 2.1 cm Discovery of potential neuroprotective compounds against chemotherapyinduced peripheral neuropathy Chang, Jang-Yang, M.D. Taiwan. Taipei Cancer Center, Taipei Medical University, Taiwan. [email protected] Chemotherapy-induced neurotoxicity is a common adverse effect of cancer treatment. No medication has been shown to be effective in the prevention or treatment of chemotherapy-induced neurotoxicity. Using minoxidil as an initial template for structural modifications in conjunction with an in vitro neurite outgrowth assay, an image-based high-content screening platform, and mouse behavior models, an effective neuroprotective agent CN016 was discovered. Our results showed that CN016 could inhibit paclitaxel-induced inflammatory responses and infiltration of immune cells into sensory neurons significantly. Thus, the suppression of proinflammatory factors elucidates, in part, the mechanism of action of CN016 on alleviating paclitaxel-induced peripheral neuropathy. Based on excellent efficacy in improving behavioral functions, high safety profiles (MTD > 500 mg/kg), and a large therapeutic window (MTD/MED > 50) in mice, CN016 might have great potential to become a peripherally neuroprotective agent to prevent neurotoxicity caused by chemotherapeutics as typified by paclitaxel. Jang-Yang Chang College of Medicine, National Defense Medical Center, Taipei, Taiwan, MD. Research fields: Development of anticancer drugs, study the mechanisms of anticancer drug resistance 4
IL.OB-01 Advances in MS-based metabolomics for natural product frontier research Sakda Khoomrung a,b,c,d aSiriraj Center of Research Excellent in Metabolomics and Systems Biology, Department of Biochemistry, Faculty of Medicine Siriraj Hospital, Mahidol University, Bangkok 10700, Thailand. bSiriraj Metabolomics and Phenomics Center, Faculty of Medicine Siriraj Hospital, Mahidol University, Bangkok 10700, Thailand. cDepartment of Biochemistry, Faculty of Medicine Siriraj Hospital, Mahidol University, Bangkok 10700, Thailand. dCenter of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400 Thailand. [email protected] In recent years, metabolomics and systems biology have been used to address various questions about natural products. Among all the compelling issues, the identification and quantification of metabolites continue to be the two greatest obstacles in the field. My presentation will center on analytical method developments, which are based on mass spectrometry (MS) and its combination with ion mobility (IM) to facilitate the identification and quantification of specialized metabolites (SMs) from medicinal plants. These include the establishment of the IM-MS library known as the Siriraj Metabolomics Data Wearhouse (SiMD) for SM screening. The quantitative analysis and prediction of novel pyranonaphthoquinone metabolites from Ventilago harmandiana by high- and low-resolution MS. In the end, I'll give an example of our current activities and how we are trying/using systems biology approaches in addition to metabolomics to identify and predict both known and novel SMs from medicinal plants. Keywords: mass spectrometry; metabolite identification; ion mobility; natural products; quantitative analysis References: 1. Wanichthanarak, K.; Nookaew, I.; Pasookhush, P.; Wongsurawat, T.; Jenjaroenpun, P.; Leeratsuwan, N.; Wattanachaisaereekul, S.; Visessanguan, W.; Sirivatanauksorn, Y.; Nuntasaen, N.; Kuhakarn, C.; Reutrakul, V.; Ajawatanawong, P. * ; Khoomrung S. * BMC Plant Biol. 2023, 23, 1-22. 2. Jariyasopit, N.; Limjiasahapong, S.; Kurilung, A.; Sartyoungkul, S.; Wisanpitayakorn, P.; Nuntasaen, N.; Kuhakarn, C.; Reutrakul, V.; Kittakoop, P.; Sirivatanauksorn, Y.; Khoomrung, S.* J. Proteome Res. 2022, 21, 2481. (Front Cover of October issue 10) 3. Limjiasahapong, S.; Kaewnarin, K.; Jariyasopit, N.; Hongthong, S.; Nuntasaene, N.; Robinson, J. L.; Nookaew, I.; Sirivatanauksorn, Y.; Kuhakarn, C.; Reutrakul, V.; Khoomrung, S.* Front. Plant Sci. 2021, 11, 2038. * = Corresponding author Sakda Khoomrung Prince of Songkla University, Thailand, B.Sc. in Education (Chemistry) Prince of Songkla University, Thailand, M.Sc., Analytical Chemistry, Major in spectrometry Technical University of Denmark, Denmark, Diploma, Major in Environmental Chemistry Karl-Franzens University, Austria, Dr. rer. nat. (Ph.D.) in Chemistry, Major in Mass Spectrometry Chalmers University of Technology, Sweden, Post Doc, Major in metabolomics and systems biology Research fields: mass spectrometry, metabolomics, biochemistry, systems biology, precision medicine 5
IL.NS-02 PHOTO Height 2.5 cm Width 2.1 cm Translational research and spin-off: novel kinase inhibitors from bench to clinic Hsing-Pang Hsieh Director/ Distinguished Investigator Institute of Biotechnology and Pharmaceutical Research National Health Research Institutes, Miaoli County, Taiwan. [email protected] Lung cancer is one of the chief causes of cancer death in the world; in addition, non-small cell lung cancer (NSCLC) accounts for 85% of the lung cancer deaths. The development of tyrosine kinase inhibitors (TKIs) targeting epidermal growth factor receptor (EGFR) have shown remarkable effects in patients but some acquired resistance after treatment. Therefore, the discovery of efficacious EGFRTKIs poses an utmost priority. Based on our achievement, we established a knowledge-based screening, followed by High Throughput Parallel Synthesis (HTPS) to synthesize more than 500 compounds. Further structure modification based on scaffold hopping approach by changing the pharmacophore moiety had led us to discover DBPR112 as a potent EGFR-TKI clinical candidate showing excellent inhibitory ability on EGFRL858R/T790M and EGFRexon20ins . DBPR112 was orally effective against the growth of human lung H1975 tumors subcutaneously xenografted in nude mice. A dramatic reduction in tumor size was noted with DBPR112 treatment, while displaying negligible body weight loss in all dosing groups. Furthermore, DBPR112 was more tolerable than afatinib in mice. To date, all pre-clinical studies were completed, and the IND application of DBPR112 was approved by US FDA and TW FDA in 2016. DBPR112 was licensed to a new startup company, AnBogne Therapeutics in 2020. Currently, the Phase 1b/2 clinical trial has been undergoing in Taiwan. References: 1. Lin, S. Y.; Hsu Yung, C.; Peng, Y. H. ; Ke, Y. Y.; Lin, W. H.; Sun,H. Y.; Kuo, F. M.; Chen, P. Y.; Lien, T. W.; Chen, C. H.; Chu, C. Y.; Wang, S. Y.; Yeh, K. C.; Chen, C. P.; Hsu, J. TA; Wu, S. Y.; Yeh, T. K.; Chen, C. T.; Hsieh, H. P.* J. Med. Chem. 2019, 62, 10108–10123. 2. Li, M. C.; Coumar, M. ; Lin, . Y.; Lin, Y. S.; Huang, G. L.; Chen, C. H.; Lien, T. W.; Wu, Y. W.; Chen, Y. T.; Chen, C. P.; Huang, Y. C.; Yeh, K. C.; Yang, C. M.; Kalita, B.; Pan, S. L.; Hsu, T. A.; Yeh, T. K.; Chen, C. T.; Hsieh, H. P.* "Development of furanopyrimidine-based orally sctive third-generation EGFR inhibitors for the treatment of non-small cell lung cancer" J. Med. Chem. 2023, 66, 2566–2588. Hsing-Pang Hsieh National Tsing Hua University, Taiwan, B.S., Chemistry National Tsing Hua University, Taiwan, M.S., Organic Chemistry State University of New York, USA, Ph.D., Organic Chemistry Research fields: drug discovery, develoment on novel anticancer drugs 6
IL.OB-02 PHOTO Height 2.5 cm Width 2.1 cm Development of solid-state Li-ion and metal-air batteries Ru-Shi Liu Department of Chemistry, National Taiwan University, Taipei, Taiwan. [email protected] To reach carbon neutrality before 2050, 80% of fossil fuels will be replaced by renewable energy to decrease CO2 emissions. In energy substitution, energy storage devices, such as Li-ion batteries, are widely used in the smart grid and electric cars. After 30 years of development, the energy density of Liion batteries reaches 300 mAh kg-1 . Solid-state Li-ion batteries are studied intensively to reach a high energy density of 500 mAh kg-1 before 2030. In a solid-state battery, solid-state electrolyte is essential in improving electrochemical performance. In this report, an development on solid-state electrolytes will be introduced.[1-4] Moreover, different rechargeable metal-Air batteries have caught much attention as one of the most intriguing methods which could simultaneously address carbon dioxide-related environmental concerns and ever-increasing sustainable energy storage demands. We will also introduce these types of batteries and give prospects compared to solid-state Li-ion batteries.[5-7] The strategy of Taiwan to development of batteries References: 1. Tong, Z. Z.; Bazri, B.; Hu, S. F.; Liu, R. S. "Interfacial chemistry in anode-free batteries: challenges and strategies" J. Mater. Chem. A 2021, 9, 7396-7406. 2. Meesala, Y.; Liao, Y. K.; Jena, A.; Yang, N. H.; Pang, W. K.; Hu, S. F.; Chang, H.; Liu, C. E.; Liao, S. C.; Chen, J. M.; Guo, X.; Liu, R. S. "An efficient multi-doping strategy to enhance Li-ion conductivity in the garnet-type solid electrolyte Li7La3Zr2O12" J. Mater. Chem. A 2019, 7, 8589–8601. 3. Jena, A.; Meesala, Y.; Hu, S. F.; Chang, H.; Liu, R. S. "Ameliorating interfacial ionic transportation in all-solid-state Liion batteries with interlayer modifications" ACS Energy Lett. 2018, 3, 2775–2795. 4. Meesala, Y.; Jena, A.; Chang, H.; Liu, R. S. "Recent advancements in Li-ion conductors for all-solid-state Li-ion batteries" ACS Energy Lett. 2017, 2, 2734–2751. 5. Iputera, K.; Huang, J. Y.; Haw, S. C.; Chen, J. M.; Hu, S. F.; Liu, R. S. "Revealing the absence of carbon in aprotic Li– CO2 batteries: a mechanism study toward CO2 reduction under a pure CO2 environment" J. Mater. Chem. A 2022, 10, 3460–3468. 6. Tong, Z.; Wang, S. B.; Fang, M. H.; Lin, Y. T.; Tsai, K. T.; Tsai, S. Y.; Yin, L. C.; Hu, S. F.; Liu, R. S. "Na–CO2 battery with NASICON-structured solid-state electrolyte" Nano Energy 2021, 85, 105972. 7. Thoka, S.; Tong, Z.; Jena, A.; Hung, T. F.; Wu, C. C.; Chang, W. S.; Wang, F. M.; Wang, X. C.; Yin, L. C.; Chang, H.; Hu, S. F.; Liu, R. S. "High-performance Na–CO2 batteries with ZnCo2O4@CNT as the cathode catalyst" J. Mater. Chem. A 2020, 8, 23974–23982. Ru-Shi Liu Soochow University, Taiwan, B.S. National Tsing Hua University, Taiwan, M.S. University of Cambridge, UK., D.Phil. Research fields: light-emitting diode (LED), fuel cells, lithium ion batteries and metal-air batteries, photodynamic therapy of nanomaterials 7
IL.OB-03 Can electronic structure provide understanding on Carbon-Carbon coupling reaction 2*CO→*OCCO on B-doped Graphyne? Poobodin Mano, a Supawadee Namuangruk, a and Kaito Takahashib aNANOTEC, National Science and Technology Development Agency, Thailand. b Institute of Atomic and Molecular Sciences, Academia Sinica Taiwan. [email protected] Due to the issue of global warming, efficient utilization of CO2 has been an important topic. Electrocatalytic reduction of CO2 to C2+ products such as C2H4, C2H5OH, or C3H7OH is an ideal solution. However, applications have been hindered by the slow kinetics due to the very high barrier of the Carbon-Carbon coupling (CC coupling) reaction. Here, we talk a look at the important electronic states of the adsorbates in the CC coupling reaction using theoretical calculations. In many previous studies, we find that for efficient lowering of the CC coupling reaction barrier, an asymmetry is required: *CO+*COH→*OC-COH, or *CO+*CHO→*OC-CHO. For the *CO+*CO→*OC-CO coupling reaction, studies have shown that difference oxidation state of copper surface can reduce the C-C coupling barrier to 0.7 eV. Here we looked at the reaction on boron doped graphyne, which is a new allotrope of carbon containing both sp2 (benzene knots) and sp (acetylene linkers) hybridization, we found the CC coupling barrier to be very low at 0.4 eV. Analyzing the bond order index along the reaction path, we found that the acetylene linkers change from sp to sp2 to sp3 hybridization as the reaction proceeds. This flexible change of the acetylene linker allows for the efficient formation of the *OCCO intermediate. We believe such a new mechanism for neutral CC coupling will open up new ideas for the efficient production of C2+ products. Keywords: density functional theory; Carbon-Carbon coupling; bond order conservation; orbital occupation References: 1. Mano, P.; Namuangruk, S.; Takahashi, K. J. Phys. Chem. C 2023, 127, 7683-7694. Kaito Takahashi Keio University, Japan, B.Sc., Chemistry Keio University, Japan, M.Sc., Chemistry Keio University, Japan, Ph.D., Chemistry Research fields: theoretical chemistry 8
IL.OB-04 Computational study of nanostructure materials for net zero climateresilient future: energy applications and carbon utilization Siriporn Jungsuttiwong Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani 34190, Thailand. [email protected] Nowadays, theoretical study has helped to develop the nanotechnology industry, discovering effective and efficient catalysts is a crucial role in the industrial production of materials and environmental protection, chemical engineers, plant managers etc. This research focuses on a theoretical study on quantum chemistry of materials for energy applications and air treatment by using density functional theory. The results of this research project can be used for screening, type of catalyst/adsorbent and provide develop a real laboratory level to assist in the design, development of high-performance catalyst/absorbent materials for the removal of pollutants from the environment including smart and sustainable energy storage applications. Keywords: clean air; energy materials; catalyst; DFT References: 1. Poldorn, P.; Wongnongwa, Y.; Zhang, R-Q.; Nutanong, S.; Tao, L.; Rungrotmongkol, T.; Jungsuttiwong, S. Int. J. Hydrog. 2023, 48, 16341. 2. Poldorn, P.; Wongnongwa, Y.; Mudchimo, T.; Jungsuttiwong, S. J. CO2 Util. 2021, 48, 101532. Siriporn Jungsuttiwong Khon Kaen University, Thailand, B.Sc., Chemistry University of UTAH, USA, M.Sc., Chemistry Kasetsart University, Thailand, Ph.D., Physical Chemistry Research fields: computational and theoretical chemistry, energy materials, catalyst 9
IL.OB-05 Semiconducting polymer photocatalysts for solar-driven hydrogen evolution Ho-Hsiu Chou Department of Chemical Engineering, National Tsing. Hua University, Hsinchu 300044, Taiwan. [email protected] By mimicking natural photosynthesis, artificial photosynthesis using polymer photocatalysts for the visible-light-driven generation of hydrogen through the splitting of water is an almost ideal process for the conversion of abundant solar energy into useable fuel in an environmentally friendly and highenergy-density manner. Photocatalytic hydrogen evolution through solar water splitting has received considerable attention due to an inexhaustible supply of solar energy. Extensive efforts have been made to prepare highly efficient photocatalytic materials. Appreciable amounts of organic semiconductors as photocatalysts have been specifically targeted to achieve outstanding photocatalytic activity because they have numerous attractive properties, including low-temperature processing, low-cost production, easily adjustable molecular structure, and tunable bandgaps that differentiate them from their inorganic counterparts. Since graphitic carbon nitride was successfully applied to photocatalytic hydrogen evolution systems in 2009, several types of research using polymeric photocatalysts, such as linear conjugated polymers, conjugated microporous polymers, polymer dots, covalent triazine frameworks, and covalent organic frameworks for hydrogen evolution have been gradually published. In a search for efficient photocatalysts that mimic such a function, here we will describe several series of newly designed polymers and polymer dots as photocatalysts for solar-driven hydrogen evolution from water. How to address the interface barrier between the polymer, water, and reagent will be included, to give a clear strategy for understanding the recent advances in this field. Keywords: semiconducting polymer; photocatalysis; solar-driven hydrogen evolution; water-splitting References: 1. (a) Chou, H.-H.; et al. Adv. Energy Mat. 2023, DOI: 10.1002/aenm.202300986. (b) Chou, H.-H.; et al. Coord. Chem. Rev. 2023, 483, 215066. (c) Chou, H.-H.; et al., Macromolecules 2023, 56, 1352–1361. 2. (a) Chou, H.-H.; et al. Nat. Commun. 2022, 13, 5460. (b) Chou, H.-H.; et al. J. Mater. Chem. A 2022, 10, 12378-12390. (c) Chou, H.-H.; et al. Appl. Catal. B: Environ. 2022, 316, 121624. (d) Chou, H.-H.; et al. J. Mater. Chem. A 2022, 10, 6641-6648. 3. (a) Chou, H.-H.; et al. Chem. Eng. J. 2021, 421, 129825. (b) Chou, H.-H.; et al. Appl. Catal. B: Environ. 2021, 298, 120577. (c) Chou, H.-H.; et al. ACS Appl. Mater. & Interfaces 2021, 13, 56554-56565. (c) Chou, H.-H.; et al. J. Mater. Chem. A 2021, 9, 6109. (d) Chou, H.-H.; et al. Appl. Catal. B: Environ. 2021, 283, 119659. (e) Chou, H.-H.; et al. ACS Photonics 2021, 8, 3125-3132. (f) Chou, H.-H.; et al. Appl. Catal. B: Environ. 2021, 285,119802. (g) Chou, H.-H.; et al. Adv. Opt. Mater. 2020, 8, 2070074. (h) Chou, H.-H.; et al. Appl. Catal. B: Environ. 2020, 268, 118436. (i) Chou, H.-H.; et al. ACS Catalysis 2018, 8, 7766-7772. Ho-Hsiu Chou B.S. National Tsing Hua University, 2005 Ph.D. National Tsing Hua University, 2010 Postdoc, Stanford University, 2013-2016 Research fields: functional materials, skin-inspired polymeric materials and devices, artificial photosynthesis, electronic skin and biomimetic sensor 10
IL.OB-06 From covalently linked peptide-membrane interactions to triggerresponsive peptidyl liposomes Hsien-Ming Lee Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan. [email protected] Antimicrobial peptides (AMPs) are recognized for their remarkable membrane-disrupting abilities. The quest to develop "smart" AMPs that can respond to specific stimuli, crucial for efficient drug delivery, has seen numerous efforts [1]. However, the outcomes of these endeavors have been limited. While controlling liposome release through smart peptides has shown promise when incubated in peptide solutions, it has proven unsuitable for drug delivery due to premature content release upon conjugation with liposomes [2,3]. In this study, we challenge the conventional understanding of binary peptide-membrane interactions (peptide-membrane interaction without conjugation) and propose a novel approach by examining peptide-membrane interactions in a unary manner, involving the conjugation of peptides and membranes. This approach provides a more comprehensive understanding of how trigger-responsive peptidyl liposomes can be generated, with significantly heightened peptide concentration against the membrane following conjugation-induced proximity. Intriguingly, we have discovered that an AMP previously considered inert to zwitterionic membranes (common in therapeutic liposomes) serves as an excellent membrane lytic backbone for smart peptidyl liposomes. Our developed peptidyl liposome demonstrates exceptional stability during the signal-waiting phase and exhibits successful release upon triggering. Building on this breakthrough, we are currently developing additional trigger-responsive peptidyl liposomes capable of responding to disease-associated enzymes. These findings offer new perspectives and opportunities in the realm of advanced drug delivery systems. References: 1. Pattni, B. S.; Chupin, V. V.; Torchilin, V. P. Chem. Rev. 2015, 115, 10938–10966. 2. Mizukami, S.; Hosoda, M.; Satake, T.; Okada, S.; Hori, Y.; Furuta, T.; Kikuchi, K. J. Am. Chem. Soc. 2010, 132, 9524-9525. 3. Mizukami, S.; Kashibe, M.; Matsumoto, K.; Hori, Y.; Kikuchi, K. Chem. Sci. 2017, 8, 3047-3053. Hsien-Ming Lee National Chao-Tung University, Taiwan, B.Sci. University of Alabama in Huntsville, USA, M. Sci. Purdue University, USA, Ph.D. Research fields: peptide-membrane interactions for membrane release and fusion, development of trigger-responsive smart biomaterials, biological applications of photon upconversion nanomaterials, protein chemical modifications 11
IL.NS-03 CRISPR Cas9-mediated ablation of pyruvate carboxylase gene in colon cancer cells inhibits growth and migration, induces apoptosis and increases sensitivity to 5-fluorouracil and glutaminase inhibitor Jarunya Ngamkham,a Siraprapa Siritutsoontorn,a Saowaluk Saisomboon,b Kulthida Vaeteewoottacharn,b and Sarawut Jitrapakdeea aDepartment of Biochemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. bDepartment of Biochemistry, Faculty of Medicine, Khon Kaen University, Khon Kaen, Thailand. [email protected] Pyruvate carboxylase (PC) is an important anaplerotic enzyme that replenishes the tricarboxylic acid cycle intermediates. It prevents the collapse of the TCA cycle upon its intermediates are removed during high anabolic demand. We have recently shown that overexpression of PC protein was associated with staging, metastasis and poor survival of colorectal cancer patients. Herein, we generated the PC knockout (PC KO) colon cancer cell lines, HT-29, by CRISPR-Cas9 technique, as a model to understand the role of this enzyme in colorectal cancer. The PC KO HT-29 cell lines had no detectable PC protein and did not show abnormal cellular or nuclear structures. However, PC KO HT-29 cells showed a 50-60% reduction in their growth rate and a 60-70% reduction in migration. The deficient growth phenotype of PC KO HT-29 cells was associated with apoptotic induction with no apparent cell cycle disruption. Down-regulation of key lipogenic enzymes, including acetyl-CoA carboxylase-1 and fatty acid synthase, was also associated with growth inhibition, suggesting that the lipogenesis is impaired. Furthermore, PC KO HT-29 cells were 50% and 60% more sensitive to 5-fluorouracil and glutaminase inhibitor, CB-839, at their IC50 concentrations, respectively, following 48 h exposure. The increased cytotoxicity of CB-839 to PC KO HT-29 cells was associated with increased PARP cleavage. However, this was not observed with PC KO cells exposed to 5-fluorouracil, suggesting that PC KO HT-29 cells were prone to CB-839-induced apoptosis. Collectively, these findings indicate that ablation of PC expression in HT-29 cells disrupts the metabolic homeostasis of cells and inhibits proliferation and migration, accompanied by apoptotic induction. Keywords: cancer metabolism; pyruvate carboxylase; glutaminase inhibitor References: 1. Phannasil, P.; Thuwajit, C.; Warnnissorn, M.; Wallace, J. C.; MacDonald, M. J.; Jitrapakdee, S. PLoS. One. 2015, 10 (6), 1−20. 2. Ngamkham, J.; Siritutsoontorn, S.; Saisomboon, S.; Vaeteewoottacharn, K.; Jitrapakdee, S. Front. Oncol. 2022, 12, 1−14. Sarawut Jitrapakdee Mahidol University, Thailand, B.Sc., Biology University of Adelaide, Australia, Ph.D., Biochemistry Research fields: cancer, cell metabolism 12
IL.NS-04 Riboflavin functionalized nanoparticles and its potential use for breast cancer treatment Wid Mekseriwattana,a,b Pablo Guardia,b Beatriz Torres Herrero,c Jesus M. de la Fuente,c Chutima Kuhakarn,d Anna Roig,b and Kanlaya Prapainop Katewongsaa,e aSchool of Materials Science and Innovation, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. b Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, Bellaterra 08193, Spain. c Instituto de Nanociencia y Materials de Aragón (INMA) CSIC-Universidad de Zaragoza & Centro de Investigación Biomédica en Red de Bioingeniería, Biomateriales y Nanomedicina (CIBER-BBN), 50018 Zaragoza, Spain. dDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, Thailand. eDepartment of Biochemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. [email protected] Breast cancer is the most prevalent cancer in women, accounting for approximately 10% of newly diagnosed cases worldwide. Superparamagnetic iron oxide nanoparticles (SPIONs) have emerged as valuable tools for the diagnosis and treatment of cancer, particularly in the development of contrast agents and magnetic hyperthermia (MH). However, achieving targeted delivery of SPIONs to cancer cells requires surface functionalization with specific ligands under mild synthesis conditions to preserve the targeting moieties. In this study, we present a novel ligand based on Riboflavin (Rf), which significantly enhances the colloidal stability of SPIONs and exhibits high targeting potential for breast cancer cells. To achieve this, we synthesized a riboflavin-citrate ester conjugate (CARf) as the ligand. We investigated the affinity of CARf for Riboflavin carrier protein (RCP) using isothermal titration calorimetry, which revealed a specific and entropy-driven binding. Furthermore, we assessed the suitability of the CARf-coated SPIONs as a theranostic platform by evaluating their responses in magnetic resonance imaging (MRI) and magnetic hyperthermia (MH). Additionally, we conducted in vitro cellular uptake experiments using MCF-7 breast cancer cells to assess the targeting efficiency against breast cancer. The characterization of the Rf-SPIONs demonstrated their excellent performance and highlighted their potential for theranostic applications in breast cancer. This research contributes to the advancement of SPION-based strategies for targeted diagnosis and treatment, offering promising prospects in the field of breast cancer research. Keywords: superparamagnetic iron oxide nanoparticles; riboflavin; breast cancer References: 1. Mekseriwattana, W.; Guardia, P.; Herrero, B. T.; de la Fuente, J. M.; Kuhakarn, C.; Roig, A.; Katewongsa, K. P. Riboflavin–citrate conjugate multicore SPIONs with enhanced magnetic responses and cellular uptake in breast cancer cells. Nanoscale Advances 2022, 4(8), 1988–1998. Kanlaya Katewongsa Mahidol University, Thailand, B.Sc., Chemistry University of Oxford, United Kingdom, D.Phil., Biochemistry Research fields: nanoparticles and its biomedical applications, bio-nano interactions 13
IL.NS-05 Anti-cancer drug discovery from natural bioactive compounds and their underlying mechanisms Arthit Chairoungdua Department of Physiology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. Toxicology Graduate Program, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. Excellent Center for Drug Discovery (ECDD), Faculty of Science, Mahidol University, Bangkok 10400, Thailand. [email protected] Cancer is one of the most common causes of death worldwide. Chemotherapy is one of the principal methods of cancer treatment. However, the effectiveness of most current anticancer drugs is limited by the adverse effect and development of drug resistance. Throughout these years, natural products remain the primary source of new anticancer drugs or lead compounds. Therefore, the discovery and development of new anticancer drugs or lead compounds from natural products are challenging. First, we investigate the anticancer activities and molecular mechanisms of altholactone and its halogenated benzoate derivatives against cholangiocarcinoma (CCA), a tumor of the biliary tract highly prevalent in Asian counties. Altholactone and its halogenated benzoate derivatives promoted CCA cell apoptosis. Furthermore, we test the effect on Topoisomerase IIα (Topo IIα) activity. Topo IIα enzyme plays essential roles in DNA replication, regulates cell survival, and is purposed as an anticancer drug target. We found that altholactone lactone and halogenated Benzoate derivatives inhibited the Topo IIα enzyme in a dose-dependent manner and markedly enhanced DNA damage. In addition, the halogenated benzoate derivatives showed a more significant inhibitory effect than the parent compound and etoposide. These results indicate that the anticancer activity of altholactone lactone and halogenated Benzoate derivatives is through the inhibition of the Topo IIα enzyme. Secondly, we investigated the anticancer activities of Cleistanthin A (CA), a natural compound from Phyllanthus taxodiifolius Beille, and derivatives (MUC573). CA and MUC573 exhibited apoptosis cytotoxic effects in two colorectal cancer cells (CRC; HCT 116 and SW480) and head and neck squamous cell carcinoma cells (HNSCC; FaDu, Cal-27, and Ca9-22). In addition, the compounds inhibited cancer cell migration and invasion at non-toxic doses. Mechanistically, CA, and MUC573 significantly inhibited V-type ATPase activity (V-ATPase) and induced apoptosis cell death. By mass spectrometry analysis, several cancer-related signaling pathways are altered after compound treatment. Our data shows us that natural bioresources are promising sources of unexploited drugs with a wide structural diversity with a variety of biological activities, including anticancer activity. Keywords: anticancer; cholangiocarcinoma; colorectal cancer; head and neck cancer; altholactone Cleistanthin A References: 1. Kitdumrongthum, S.; Reabroi, S.; Suksen, K.; Tuchinda, P.; Munyoo, B.; Mahalapbutr, P.; et al. “Inhibition of topoisomerase IIalpha and induction of DNA damage in cholangiocarcinoma cells by altholactone and its halogenated benzoate derivatives” Biomed. Pharmacother. 2020, 127, 110149. 2. Jearawuttanakul, K.; Khumkhrong, P.; Suksen, K.; Reabroi, S.; Munyoo, B.; Tuchinda, P.; et al. “Cleistanthin A induces apoptosis and suppresses motility of colorectal cancer cells” Eur. J. Pharmacol. 2020, 889, 173604. Arthit Chairoungdua Khon Kaen University, Thailand, B.Sc., Nursing Mahidol University, Thailand, M.Sc., Toxicology Kyorin University, Japan, Ph.D., Medical Science Research fields: cancer research, extracellular vesicles, nanovesicles, toxicology 14
IL.NS-06 Enantioselective synthesis of 1-aryl tetrahydroisoquinolines by the rhodium-catalyzed reaction of 3,4-dihydroisoquinolinium tetraarylborates Wei-Sian Li, a Ting-Shen Kuo, a Ping-Yu Wu, a Chien-Tien Chen, b and Hsyueh-Liang Wua aDepartment of Chemistry, National Taiwan Normal University, Taipei, 11677, Taiwan. bDepartment of Chemistry, National Tsing-Hua University, Hsinchu, 30013, Taiwan. [email protected] The 1-aryl tetrahydroisoquinolines (1-aryl THIQs) are omnipresent in biologically active molecules. Here we report on the direct asymmetric synthesis of these valuable compounds via the reaction of 3,4-dihydroisoquinolinium tetraarylborates. The dual roles of anionic tetraarylborates, which function as both prenucleophiles and stabilizers of 3,4-dihydroisoquinolinium cations, enable this rhodium(I)-catalyzed protocol to convergently provide enantioenriched 1-aryl THIQs in good yields (≤95%) with ≤97% ee, as demonstrated by the formal synthesis of (−)-solifenacin and the facile synthesis of (−)-cryptostyline I. Keywords: rhodium-catalyzed; 1-arylisoquinolines; solifenacin; cryptostyline I References: 1. Li, W.-S.; Kuo, T.-S.; Wu, P.-Y.; Chen, C.-T.; Wu, H.-L. Org. Lett. 2021, 23, 1141–1146. Hsyueh-Liang Wu National Tsing-Hua University, Taiwan, B.Sc., Chemistry National Tsing-Hua University, Taiwan, Ph.D., Chemistry Research fields: asymmetric catalysis, natural product synthesis N R1 [RhCl(C2H4)2]2 / L* (3.0 mol % of Rh) dioxane, 100 °C N R1 Ar BAr4 R 3 R2 R2 R 3 28 examples up to 95% yield up to 97% ee Ph H N O L* 15
IL.NS-07 PHOTO Height 2.5 cm Width 2.1 cm Nitrogen heterocycles: synthesis through cascade cyclization and their potentials as drug prototypes Jatuporn Meesin, a Jongkonporn Phetcharawetch, a Thikhamporn Uppalabat,a Darunee Soorukram,a Pawaret Leowanawat,a Vichai Reutrakul,a Thitinan Aiebchun, b Thanyada Rungrotmongkol, b and Chutima Kuhakarna aDepartment of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. bCenter of Excellence in Biocatalyst and Sustainable Biotechnology, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand. [email protected] Among numerous diseases and illnesses, cancer has emerged at the top of the list as the leading cause of death. Due to the important threats of cancer diseases, efforts are now being focused on finding novel pharmaceuticals for cancer treatment. Several anticancer drugs are nitrogen-containing heterocycles such as afatinib, erlotinib (tyrosine kinase inhibitors) and camptothecin (a topoisomerase inhibitor). Nitrogen hetereocycles present in numerous natural products, biologically active molecules and functional materials. A number of which showed numerous pharmacological properties. This presentation highlights our recent research accomplishment on the synthesis of nitrogen heterocycles including indoles, indeno[1,2‑c]quinolines, and indolo[1,2-a]quinolines promoted by S-center radicals including sulfonyl and trifluoromethylthio radicals. Selected series of our in-house compounds were screened for their potential as anticancer drug candidates targeting epidermal growth factor receptor (EGFR) tyrosine kinase (TK). Keywords: nitrogen heterocycles; cascade reactions; sulfones; isonitriles; fluorine References: 1. (a) Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Leowanawat, P.; Kuhakarn, C. Org. Biomol. Chem. 2017, 15, 3662−3669. (b) Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Leowanawat, P.; Saithong, S.; Kuhakarn, C. Org. Lett. 2017, 19, 6546−6549. 2. Phetcharawetch, J.; Betterley, N. M.; Reutrakul, V.; Soorukram, D.; Leowanawat, P.; Kuhakarn, C. J. Fluor. Chem. 2021, 250, 109878. 3. Uppalabat, T.; Hassa, N.; Sawektreeratana, N.; Leowanawat, P.; Janthakit, P.; Nalaoh, P.; Promarak, V.; Soorukram, D.; Reutrakul, V. Kuhakarn, C. J. Org. Chem. 2023, 88, 5403−5419. 4. Hengphasatporn, K.; Aiebchun, T.; Mahalapbutr, P.; Auepattanapong, A.; Khaikate, O.; Choowongkomon, K.; Kuhakarn, C.; Meesin, J.; Shigeta, Y.; Rungrotmongkol, T. ACS Omega 2023, 8, 19645−19655. Chutima Kuhakarn Mahidol University, Thailand, B.Sc., Chemistry Mahidol University, Thailand, M.Sc., Organic Chemistry University of Wisconsin, Madison, USA, Ph.D., Chemistry Research fields: synthetic methodology, structure modification 16
IL.OB-07 Oxidation reactions of HMF and furfural Ekasith Somsook, Thinnaphat Poonsawat, Kaleeswari Kalimuthu, Nattapong Kongcharoen, Tassadee Titimahasan, Harshit Shukla, a Minh Huy Hoang Tran, Sutthita Baiphokthong, Natcha Temnuch, and Peerapong Promcharoen NANOCAST Laboratory, Center for Catalysis Science and Technology (CAST), Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, 272 Rama VI Rd., Ratchathewi, Bangkok 10400, Thailand. [email protected] Integrated biorefineries have been receiving more attention to increase the demand responses in bio-green-circular economy for solving the environmental global issues leading to the sustainable development. In this report, 2,5-hydroxymethyl furfural (HMF) and furfural are selected as chemical platforms to be investigated for the productions of 2,5-furandicarboxylic acid (FDCA) and succinic acid (SA), respectively. For the HMF chemical platforms, metal-oxide catalysts will be reported for the oxidation of HMF to FDCA. HMF is an unstable molecule, and it is transformed to humin in an acidic solution or a high concentrated condition. The stabilization of HMF by the structure modification of HMF or the addition of other metal ions will be reported. For the furfural chemical platform, the oxidation of furfural to succinic acid (SA) in the presence of hydrogen peroxide as oxidizing agent will be reported. However, the major product of the oxidation of furfural in this condition was maleic acid. Keywords: oxidation; HMF; FDCA; furfural; maleic acid; succinic acid Ekasith Somsook Mahidol University, Thailand, B.Sc., Chemistry University of Wisconsin, Madison, USA, Ph.D., Chemistry Research fields: development of catalysts for biorefinery and chemical recycling of plastics 17
IL.OB-08 X-ray absorption spectroscopy: the state of the art synchrotron-based characterization for energy materials Pinit Kidkhunthod, a Somboonsub Rodporn, a Thanchaya Chubkhuntod, a Saroj Rujirawat, a Rattikorn Yimnirun, b and Santi Maensiric aSynchrotron Light Research Institute, 111 University Ave., Muang, Nakhon Ratchasima 30000, Thailand. bSchool of Energy Science and Engineering (ESE), Vidyasirimedhi Institute of Science and Technology (VISTEC), Rayong 21210, Thailand. cSchool of Physics, Suranaree University of Technology, Muang, Nakhon Ratchasima 30000, Thailand. [email protected] The investigation of the local geometric and electronic structure of probing element in bulk samples is the most extensive field of application in X-ray Absorption Spectroscopy (XAS). XAS consists of two main regions which are X-ray Absorption Near Edge Structure (XANES) and Extended X-ray Absorption Fine Structure (EXAFS). The former region is used to explain the local geometry and oxidation states of selected element in a sample whilst the latter one is used to address the local structure around probing element in samples. In my talk, the introduction of XAS and applications of synchrotron-based XAS on advanced functional materials such as energy materials, Li-ion and K-ion battery and catalysts will be introduced in order to understand the structure and function relationship of these materials. Keywords: X-ray absorption spectroscopy (XAS); XANES, EXAFS; structure and function Dr. Pinit Kidkhunthod is currently as Chief of Synchrotron Research and Applications Division, Synchrotron Light Research Institute (Public Organization), Thailand. Dr. Pinit has also been working as beamline scientist focusing on X-ray absorption spectroscopy (XAS) technique since 2012. His research interest is in the fields of structural studies of advanced functional materials such as catalysts, energy materials and novel amorphous materials for energy storage applications using XAS-based technique. Dr. Pinit Kidkhunthod received his BSc. (Physics), first class honors 3.99 from Khon Kaen University, Thailand in 2007, and Ph.D. (Physics) from Bristol University, U.K in 2012. Recently, Dr. Kidkhunthod has received research grants for young scientist from Thailand Research Fund (TRF2013) and Ministry of Science and Technology (2014) Additionally, he has been awarded the funding support from the NSRF, Thailand, via the Program Management Unit for Human Resources & Institutional Development, Research and Innovation 2021 and funding for Talented Mid-Career Researchers from National Research Council Thailand (NRCT) 2022-2024. Recently, he has been awarded the adjunct Professor at the Shenzhen Institute of Advanced Technology, Chinese Academy of Science (SIAT-CAS during 2018-present) and Visiting Scientist position at CAS (PIFI program) in 2021 and 2023. Additionally, he has been successfully awarded the Outstanding Young Materials Researcher Award 2022 from the Materials Research Society Thailand (MRS-Thailand). Currently, he has been the author and co-author of over 260 papers in scopusbased journals (H-index = 36) for structural studies of advanced functional materials using XAS technique. 18
P.OB-01 CeMnOx yolk-shell microspheres for the aerobic oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran Warinda Tirdtrakool, Hemmarat Kreethatorn, and Jonggol Tantirungrotechai Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. [email protected] 2,5-Diformylfuran (DFF) is useful as a fuel additive and can be synthesized from the oxidation of 5-hydroxymethylfurfural (HMF), a biomass-derived platform chemical. Manganese oxide (MnO2) has been widely employed as an aerobic oxidation catalyst due to its low cost and environmental friendliness. In addition, the presence of cerium in manganese oxide can lead to better oxygen storage property and eventually improve the catalytic oxidation ability. Therefore, in this study, cerium manganese oxide (CeMnOx) samples were prepared by the redox-precipitation method to obtain porous yolk-shell microspheres with Ce/Mn ratio of 0.02, 0.04, 0.08, 0.2, and 0.4. All samples were fully characterized and their catalytic behavior for the aerobic oxidation of HMF to DFF was investigated. Addition of Ce into the structure of MnOx affected several physical properties as well as the oxidation ability of the catalysts. The results showed that the sample with Ce/Mn ratio of 0.02 performed the best with 81% HMF conversion and 98% DFF selectivity. Keywords: cerium manganese oxide; aerobic oxidation; 5-hydroxmethylfurfural; 2,5-difoymylfuran; biorefinery References: 1. Chutimasakul, T.; Tirdtrakool, W.; Na Nakhonpanom, P.; Kreethatorn, H.; Jaruwatee, P.; Bunchuay, T.; Tantirungrotechai, J. ChemistrySelect, 2022, 7, e202203028. 2. Kreethatorn, H., Ph.D. Dissertation, Mahidol University, 2016. Jonggol Tantirungrotechai Princeton University, USA, A.B., Chemistry University of California at Berkeley, USA, Ph.D., Chemistry Research fields: heterogeneous catalysis and inorganic materials 19
P.OB-02 PHOTO Height 2.5 cm Width 2.1 cm Asymmetric total synthesis of ventilanone A and ventilanone B, two naturally occurring pyranonaphthoquinones from Ventilago harmandiana Pramchai Deelertpaiboon, Sopanat Kongsriprapan, Suppachai Krajangsri, Nolan M. Betterley, Chutima Kuhakarn, and Vichai Reutrakul Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, Thailand. [email protected] The Ventilago genus belongs to the family Rhamnaceae and various plants in the Ventilago genus were used in traditional medicines. Ventilago harmandiana Pierre, a climber, is endemic to Thailand and is only found in Phang-Nga Province located in the Southern part of Thailand. The decoction of V. harmandiana was traditionally used for treatment of diabetes, wounds, chronic inflammation, psoriasis and AIDS.1 Pharmacological evaluation of the methanolic extract of the heartwoods of V. harmandiana displayed promising anti-inflammatory effects in both acute and chronic inflammatory assays.2 As a part of our continuing search for new biologically active lead structures from plants for drug development, we recently disclosed the isolation of nineteen chemical constituents from V. harmandiana, including ventilanone A and ventilanone B.3 The asymmetric synthesis of novel pyranonaphthoquinones ventilanone A and ventilanone B was accomplished employing L-rhamnose and gallic acid as the starting materials.4 The key reactions are the utilization of a newly introduced reagent, PhSCF2H/SnCl4, for the formylation of sterically hindered aromatics containing an electron-withdrawing methyl ester, and the efficient Hauser annulation of phenylthiophthalides with optically active C-1 glycal derived from L-rhamnose. The synthetic methodologies developed solved the longstanding problem in formylation of sterically hindered aromatics containing electron-withdrawing groups, and are applicable for the synthesis of other analogues with substituents at the aromatic and pyran rings. Keywords: Hauser annulation, pyranonaphthoquinones, Ventilago harmandiana Pierre, ventilanones References: 1. (a) Balakrishnan, N.; Singh, B. Asian J. Chem. 2013, 25, 2438. (b) Periyasamy, K.; Kaliyaperumal, S. Int. J. Curr. Pharm. Res. 2016, 8, 16. (c) Caichompoo, W.; Zhang, Q.-Y.; Thangthaisong, T.; Phadungkit, M. Int. J. Pharm. Res. 2012, 89. (d) Lipipun, V.; Kurokawa, M.; Suttisri, R.; Taweechotipatr, P.; Pramyothin, P.; Hattori, M.; Shiraki, K. Antiviral Res. 2003, 60, 175. 2. (a) Panthong, A.; Kanjanapothi, D.; Taesotikul, T.; Phankummoon, A.; Panthong, K.; Reutrakul, V. J. Ethnopharmacol. 2004, 91, 237. (b) Molee, W.; Phanumartwiwath, A.; Kesornpun, C.; Sureram, S.; Ngamrojanavanich, N.; Ingkaninan, K.; Mahidol, C.; Ruchirawat, S.; Kittakoop, P. Chem. Biodivers. 2018, 15, 1700537. 3. Panthong, K.; Hongthong, S.; Kuhakarn, C.; Piyachaturawat, P.; Suksen, K.; Panthong, A.; Chiranthanut, N.; Kongsaeree, P.; Prabpai, S.; Nuntasaen, N.; Reutrakul, V. Phytochemistry 2020, 169, 112182. 4. Deelertpaiboon, P.; Kongsriprapan, S.; Krajangsri, S.; Betterley, N. M.; Kuhakarn, C.; Reutrakul, V. Synthesis 2022, 52, 3093. Nolan M. Betterley University of California – Santa Cruz, USA, B.Sc., Biochemistry and Molecular Biology Mahidol University, Thailand, Ph.D., Organic Chemistry Research fields: synthetic methodology, total synthesis 20
P.OB-03 PHOTO Height 2.5 cm Width 2.1 cm The bioactive compounds from heartwoods and stem barks of Ventilago harmandiana Pierre Suwannee Saisin, a Chutima Kuhakarn, a Sariyarach Thanasansurapong, a Arthit Chairoungdua, b Kanoknetr Suksen, b Radeekorn Akkarawongsapat, c Chanita Napaswad, c Samran Prabpai, a Kanda Panthong,d Sakchai Hongthong, e Narong Nuntasaen, f and Vichai Reutrakula aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. bDepartment of Physiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. cDepartment of Microbiology, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. dDivision of Physical Sciences and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand. eDivision of Chemistry, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand. fThe Forest Herbarium National Park, Wildlife and Plant Conservation Department, Ministry of Natural Resources and Environment, Bangkok 10900, Thailand. [email protected] Known as “Khon Tee Dum” in Thai, Ventilago harmandiana belongs to the Rhamnaceae family and can be found in the sandy mountain areas located in the southern part of Thailand. Previous ethnopharmacological study of the MeOH extracts of heartwoods and stem barks of V. harmandiana indicated that they showed antiinflammatory activity in both acute and chronic inflammatory assays. The present work described novel compounds isolated from the heartwoods and the stem barks of V. harmandiana. Ten pyranonaphthoquinones, ventilanones A−J (1–10) as well as an anthraquinone, ventilanone K (11) were isolated from the heartwoods. Five pyranonaphthoquinones, ventilanones L−P (12–16) along with two naphthoquinones, ventilanone Q (17) and ventilanone R (18) were obtained from the stem barks. In addition, ventilanones A−E (1–5) and G–I (7–9) were also found in the stem barks. The biological activities including anti-HIV-1 activity using syncytium inhibition assay, cytotoxicity and anti-inflammatory were evaluated. Keywords: Ventilago harmandiana, pyranonaphthoquinone, naphthoquinone, anti-HIV-1, cytotoxicity References: 1. Panthong, A.; Kanjanapothi, D.; Taesotikul, T.; Phankummoon, A.; Panthong, K.; Reutrakul, V. J. Ethnopharmacol. 2004, 91, 237‒242. 2. Panthong, K.; Hongthong, S.; Kuhakarn, C.; Piyachaturawat, P.; Suksen, K.; Panthong, A.; Chiranthanut, N.; Kongsaeree, P.; Prabpai, S.; Nuntasaen, N.; Reutrakul, V. Phytochemistry 2020, 169, 112182. 3. Saisin S.; Saisin K.; Hongthong S.; Kuhakarn C.; Thanasansurapong S.; Chairoungdua A.; Suksen K.; Akkarawongsapat R.; Napaswad C.; Prabpai S.; Nuntasaen N.; Reutrakul V. J. Nat. Prod. 2023, 86, 498−507. Sariyarach Thanasansurapong Ramkhamheang University, Thailand, B.Sc., Chemistry Mahidol University, Thailand, M.Sc., Organic Chemistry Mahidol University, Thailand, Ph.D., Organic Chemistry Research fields: bioactive natural products, pharmaceutical chemistry, drug discovery 21
P.OB-04 Green solution plasma-based preparation of rGO-MnO2 nanocomposite as electrode material for energy storage device Thitaree Pimklang, a Anyarat Watthanaphanit, a and Pasit Pakawatpanuruta b c aDepartment of Chemistry, Faculty of Science, Mahidol University, Ratchathewi, Bangkok 10400, Thailand. bCenter of Sustainable Energy and Green Materials, Faculty of Science, Mahidol University, Ratchathewi, Bangkok 10400, Thailand. cCenter of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Ratchathewi, Bangkok 10400, Thailand. [email protected] Several studies have reported different methods for preparing reduce graphene oxide (rGO) and manganese dioxide (MnO2) nanocomposite for energy storage applications. Graphene oxide (GO) is a popular choice for the precursor of the process owing to its hydrophilic property. However, the low electrochemical conductivity of GO remains one of the important drawbacks. Although this limitation could be resolved by reducing GO component of the composite to a more conductive rGO, such an approach often requires stringent conditions that include detrimental chemicals and high temperature and pressure. Herein, a green, one-pot, solution plasma (SPP)-based synthesis route for rGO-MnO2 nanocomposite using rGO as a precursor was introduced. The SPP was utilized to generate plasma that consists of reactive species, such as H. and OH., within the potassium permanganate (KMnO4) solution to convert permanganate ions (MnO4 - ) to MnO2 nanoparticles [1], eventually resulting in electrostatic deposition of MnO2 onto the rGO sheets. This work demonstrated that the composite could be successfully synthesized from the precursor rGO within 10 min of SPP under ambient processing condition. In addition, the rGO-MnO2 nanocomposite also exhibited satisfactory specific capacitance in three-electrode configuration with 1 M Na2SO4 aqueous electrolyte at a scan rate of 5 mV s-1 . Keywords: reduce graphene oxide; manganese dioxide; solution plasma; nanocomposite; energy storage References: 1. Kim, H.; Watthanaphanit, A.; Saito, N. RSC Adv. 2016, 6, 2826–2834. Thitaree Pimklang Khon Kaen University, Thailand, B.Sc., Chemistry Mahidol University, Thailand, Ph.D. student, Chemistry Research fields: energy storage, solution plasma process, physical chemistry 22
P.OB-05 Interlayer engineering of Ti3C2Tx MXene using graphitic carbon nitride for flexible supercapacitor Manopat Depijan, a Kanit Hantanasirisakul, b and Pasit Pakawatpanuruta aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, 272 Rama VI Road, Ratchathewi, Bangkok 10400, Thailand. bCentre of Excellence for Energy Storage Technology (CEST), Department of Chemical and Biomolecular Engineering, School of Energy Science and Engineering, Vidyasirimedhi Institute of Science and Technology, Wangchan Valley, Rayong 21210 Thailand. [email protected] Ti3C2Tx-based supercapacitor has recently received wide attention in the energy storage community due to its outstanding performance. However, the achieved capacitance in most neutral electrolytes was still unsatisfactory because of low ion diffusion efficiency as a result of limited interlayer spacing within Ti3C2Tx. In this work, the protonated g-C3N4 (pg-C3N4) was doped at the Ti3C2Tx interface using a layer-by-layer assembling process. The multilayered freestanding film indicated the pillaring effect after pg-C3N4 was introduced. The elemental analysis revealed the presence of N atom within Ti3C2Tx, which indicated successful incorporation of pg-C3N4. The electrochemical characterization of pg-C3N4/Ti3C2Tx demonstrated the expanded potential window up to 1.1 V with an improved specific capacitance of about 95 F g-1 at 2 mV s-1 in a neutral MgSO4 electrolyte. The higher capacitance could be ascribed to better ion diffusion that resulted from the enlargement in d-spacing. Moreover, our analysis found that pg-C3N4 could increase the diffusion-controlled contribution or pseudocapacitive character when compared to Ti3C2Tx. Keywords: titanium carbide MXene; graphitic carbon nitride; neutral electrolyte; interlayer engineering; layer-by-layer assembly References: 1. Zhao, M.; Ren, C. E.; Ling, Z.; Lukatskaya, M. R.; Zhang, C.; Aken, K. L. V.; Barsoum, M. W.; Gogotsi, Y. Flexible MXene/Carbon Nanotube Composite Paper with High Volumetric Capacitance. Adv. Mater. 2015, 27, 339–345. 2. Shi, M.; Xiao, P.; Lang, J.; Yan, C.; Yan, X. Porous g-C3N4 and MXene Dual-Confined FeOOH Quantum Dots for Superior Energy Storage in an Ionic Liquid. Adv. Sci. 2020, 7, 1901975. Manopat Depijan University of Phayao, Thailand, B.Sc., Chemistry University of Phayao, Thailand, B.Ed., Chemistry Mahidol University, Thailand, M.Sc. student, Chemistry Research fields: energy storage, electrocatalysis Magnesium ion 23
P.OB-06 Heterostructure of NiV layered double hydroxide with Ti3C2Tx MXene for high-performance psuedocapacitors Farman Ali, Manopat Depijan, and Pasit Pakawatpanurut Department of Chemistry, Centre of Excellence for Innovation in Chemistry (PERCH-CIC), and Centre of Sustainable Energy and Green Materials, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. [email protected] Ni-V layered double hydroxides (LDH) have gained significant attention as electrode materials in the field of energy storage devices, such as batteries and supercapacitors, owing to their low cost, high specific capacitance, and unique tuneable two-dimensional (2D) layer structure. However, poor electrical conductivity and unsatisfactory cyclic stability have been recognized as the main factors constraining the electrochemical performance of LDH. Hence, to overcome these intractable problems, there is a need for an effective approach to fabricate heterostructures with highly electrically conductive and redox-active materials to produce highperformance supercapacitors. Ti3C2Tx MXene, showing its unique lamellar structure, rich surface chemistry, and exceptional electrical conductivity (~104 S/cm), can be considered a suitable candidate. A facile hydrothermal process was used to fabricate a heterostructure of Ni-V LDH with highly conductive two-dimensional exfoliated Ti3C2Tx nanosheets. Negatively charged single- or few-layered exfoliated Ti3C2Tx MXene nanoflakes provided abundant heterogeneous nucleation sites for electrostatic interactions with positively charged Ni-V LDH nanosheets. The results of various characterization techniques, including XRD, FTIR, Raman spectroscopy, and Zetasizer, have confirmed the successful synthesis of Ni-V/Ti3C2Tx MXene heterostructures. For electrochemical performance, cyclic voltammetry was performed to evaluate the specific capacitance (Csp) at different scan rates of 5 mV s-1 , 10 mV s-1 , 20 mV s-1 , 30 mV s-1 , 50 mV s-1 , 75 mV s-1 , and 100 mV s-1 in a potential window of 0.45 V. The electrode coated with the Ni-V/Ti3C2Tx MXene heterostructure in a three-electrode cell configuration exhibited an excellent Csp of 1235 F/g at a scan rate of 10 mV s-1 . Galvanostatic charge-discharge, electrochemical impedance spectroscopy, and other physical characterizations of heterostructures are underway for better electrochemical and structural studies. Keywords: supercapacitors; Ni-V layered double hydroxide; Ti3C2Tx MXene; electrical conductivity; cyclic stability References: 1. Anasori, B.; Lukatskaya, M. R.; Gogotsi, Y. 2D Metal Carbides and Nitrides (MXenes) for Energy Storage. Nat. Rev. Mater. 2017, 2, 16098. 2. Tyagi, A.; Joshi, C. M.; Shah, A.; Thakur, V. K.; Gupta, R.K. Hydrothermally Tailored Three-Dimensional Ni-V Layered Double Hydroxide Nanosheets as High-Performance Hybrid Supercapacitor Applications. ACS Omega 2019, 4, 3257-326. Farman Ali Government College University, Pakistan, B.Sc. Physical Chemistry Mahidol University, Thailand, M.Sc. Physical Chemistry Research fields: biosensor fabrication, energy storage by electrochemical supercapacitors 24
P.OB-07 Aerobic oxidation of 5-hydroxymethylfurfural (HMF) to 2,5- furandicarboxylic acid (FDCA) catalyzed by K+ and Ca2+ intercalated nanolayered manganese dioxide (K-MnO2 and Ca-MnO2) Thinnaphat Poonsawat and Ekasith Somsook NANOCAST Laboratory, Center for Catalysis Science and Technology (CAST), Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, 272 Rama VI Rd., Ratchathewi, Bangkok 10400, Thailand. [email protected] Effect of alkali (K+ ) and alkaline earth (Ca2+) into the structural manganese dioxide was studied in the selective oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) under the high pressure of O2 (0.5 MPa) in the presence of NaHCO3. The promising results were investigated that located Ca2+ ion facilitated an important role to improve the surface area up to 173 m2 /g and to accelerate the FDCA yield up to 85%. Interestingly, the K-MnO2 and Ca-MnO2 were able to be a good candidate for considering in term of stability and reusability without significant loss in activity at least 3 times. Increasing the edge of knowledge can be utilized to develop of the current benchmark for FDCA production. Keywords: HMF oxidation; potassium manganese dioxide; calcium manganese dioxide; FDCA Thinnaphat Poonsawat Silpakorn University, Thailand, B.Sc., Major, Chemistry Mahidol University, Thailand, M.Sc., Major, Chemistry Mahidol University, Thailand, Ph.D. student, Chemistry Research fields: sustainability and molecular dynamics 25
P.OB-08 Oxidation of furfural to maleic acid and succinic acid through Fenton type reaction using iron oxide catalyst Peerapong Promcharoen, a Sutthita Baipokthong, b and Ekasith Somsooka aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. b Department, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. [email protected] The Fenton reaction is popular for removing organic waste through an oxidation reaction in water to CO2 gas with H2O2, and H2O2 can decompose under sunlight to O2 gas and water. This work was a study of the Fenton reaction between iron oxide catalysts and H2O2 for the oxidation of furfural to succinic acid and maleic acid by comparison of the properties of species of iron oxide catalysts. In previous work in 2016, formic acid was used as a catalyst coupled with H2O2 for the oxidation of furfural to succinic acid and maleic acid1 , and in 2022, Sn-Beta catalyst and H2O2 were used for the oxidation of furfural to succinic acid2 . Which, the iron oxide catalysts studied have 4 kinds are Fe2O3, -Fe2O3, -Fe2O3, and Fe3O4, and their characteristics were confirmed with TEM, XRD, XPS, and BET. Those iron oxide catalysts receive succinic acid and maleic acid from furfural oxidation, and %yields of succinic acid and maleic acid and %recovery of furfural were analyzed with HPLC. Scheme 1. Furfural oxidation to succinic acid and maleic acid through the Fenton reaction Keyword: furfural, succinic acid, maleic acid, oxidation, Fenton reaction, iron oxide catalysts References: 1. Li, X.; Lan, X.; Wang, T. Selective oxidation of furfural in a bi-phasic system with homogeneous acid catalyst. Catalysis Today 2016, 276, 97-104. DOI: 10.1016/j.cattod.2015.11.036. 2. Palai, Y. N.; Shrotri, A.; Fukuoka, A. Selective Oxidation of Furfural to Succinic Acid over Lewis Acidic Sn-Beta. ACS Catalysis 2022, 12, 3534-3542. DOI: 10.1021/acscatal.1c05348. Peerapong Promcharoen Suratthani Rajabhat University, Thailand, B.Sc., Chemistry Mahidol University, Thailand, Ph.D. student, Chemistry Research fields: Inorganic chemistry and catalysts 26
P.OB-09 Oxidation of 5-HMF to FDCA catalyzed by N-doped carbon supported non-noble metal catalyst Kaleeswari Kalimuthu, and Ekasith Somsook Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. [email protected] Biomass derived 2,5-furandicarboxylic acid (FDCA) is one of the most important and promising candidates in the furan family because of its multi-functionality based on the structure and di-acidic side chains. FDCA has recently gained a lot of attention due to its wide variety of applications, especially as a substitute for terephthalic acid obtained from petrochemicals in the production of useful polymers. In previous work1 , suggested that the selection of precursors plays a crucial role in the bimetallic catalysts. In the light of that, the N-doped carbon supported non-noble bimetal catalysts were synthesized by simple solid grinding and pyrolyze method using different precursors with different ratios of metals for the HMF oxidation to FDCA. The characteristics of the catalysts were studied and confirmed by XRD, TEM, SEM, BET, XPS, ICP-MS, and Raman spectroscopy. The impact factors of Base equivalency, oxygen pressure, reaction time and temperature were also investigated for this work. Scheme 1: Oxidation of 5-HMF to FDCA through N-doped carbon supported non-noble metal catalyst Keywords: N-doped carbon; bimetallic catalyst; FDCA; HMF oxidation; non-noble metal catalyst Kaleeswari Kalimuthu Bharathiar University, India, B.Sc., Chemistry Bharathiar University, India, M.Sc., Chemistry Mahidol University, Thailand, Ph.D. student, Chemistry Research fields: inorganic chemistry, catalysis science and technology 27
P.OB-10 Traveling wave ion mobility-derived collision cross section database for plant specialized metabolites: An application to Ventilago harmandiana Pierre Narumol Jariyasopit, a,b Suphitcha Limjiasahapong, b Alongkorn Kurilung, a Sitanan Sartyoungkul, a Pattipong Wisanpitayakorn, a,b Narong Nuntasaen, c Chutima Kuhakarn, c Vichai Reutrakul, c Prasat Kittakoop, d,e Yongyut Sirivatanauksorn, b and Sakda Khoomrunga,b,c aMetabolomics and Systems Biology, Department of Biochemistry, Faculty of Medicine Siriraj Hospital, Mahidol University, Bangkok 10700, Thailand. bSiriraj Metabolomics and Phenomics Center, Faculty of Medicine Siriraj Hospital, Mahidol University, Bangkok 10700, Thailand. cCenter of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, Thailand. dChulabhorn Graduate Institute, Program in Chemical Sciences, Chulabhorn Royal Academy, Laksi, Bangkok 10210, Thailand. eChulabhorn Research Institute, Laksi, Bangkok 10210, Thailand. [email protected] Plant natural products contain a variety of constituents, successful identification of bioactive compounds requires advances in technologies. Recently, a combination of ion mobility and mass spectrometry has increasingly been adopted to improve metabolite identification due to the ability of IM in providing an additional molecular property, CCS value, that is specific to a molecule. To facilitate the integration of CCS measurement into the conventional MS-based metabolomics workflows, it requires large experimental CCS databases of metabolites. In this work, we aimed to provide another source of experimental CCS values of specialized metabolites gathered from tropical plants over years. We developed an UPLC-TWIMS-QTOF method to characterize 112 plant specialized metabolites, including 15 specialized metabolites that were isolated in-house and not commercially available. The established MS and CCS database provides reliable and reproducible accurate m/z, retention times, fragment ions, and CCS values of 207 adducts (ESI+ and ESI-). We demonstrated that the CCS measurement is robust and reliable, yielding small variations when performed within a day and, at least, for three days. Regarding the analysis of isomeric compounds, most of the isomeric compounds could be separated by retention times, highlighting the importance of combining chromatography, IM, and MS for the analysis of complex samples. The IM-MS of the specialized metabolites exhibited good linear relationship, but we observed no distinct trendlines among classes. To validate the established database, we applied the established database to extend metabolite coverage of Ventilago harmandiana. The identified metabolites show relatively low average mass error (2.2 ± 2.6 ppm) and ΔCCS% (0.9% ± 0.8%). In addition to PNQs which are important metabolites in V. harmandiana, we were able to identify, for the first time, flavonoids, xanthone, naphthofuran, and protocatechuic acid through targeted analysis. A distinct IM-MS profile of a group of features suggested the presence of organonitrogen compounds and lipid and lipid-like molecules. Keywords: Ventilago harmandiana; collision cross section; TWCCSN2, traveling wave ion mobility; TWIMS; mass spectrometry; metabolomics; natural products Narumol Jariyasopit Oregon State University, U.S.A., B.Sc., Chemistry Oregon State University, U.S.A., Ph.D., Analytical Chemistry Research fields: mass spectrometry, metabolomics, sir research 28
P.OB-11 Development of high catalytic performamce for carbon dioxide conversion to value-added product: A DFT study Rattanawalee Rattanawan, Suphitchaya Trakunhiranrak, and Siriporn. Jungsuttiwong Department of Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, 34190, Thailand. [email protected] Carbon dioxide (CO2) is a major greenhouse gas that can be released from engine of vehicles and industry. The increasing amount of CO2 gas resulting in global warming effect. This harmful gas could be conversed to value-added compound via the CO2 hydrogenation to formic acid (CO2 + H2 → HCOOH). In this research, the mechanism of CO2 hydrogenation over the single-atom catalysts (SACs) supported on graphitic carbon nitride (g-C3N4) have been investigated by means of Density functional Theory (DFT). The Cu atom was decorated on g-C3N4 monolayer to construct the SACs catalyst model. Firstly, the adsorption of CO2, H2 molecule, and co-adsorption complex (Co-Ads) were calculated. The CO2 hydrogenation can be occurred by Co-adsorption pathway via two important intermediates, namely (i) formate (HCOO) and (ii) carboxylate (COOH). According to DFT calculation, it was found that HCOOH formation can be produced via HCOO key intermediate over Cu-g-C3N4 catalyst. The hydrogen dissociation step is the rate determining step with activation barrier of 0.64 eV. This work could be provided a more understanding of CO2 conversion and the good potential of Cu-g-C3N4 catalysts. Keywords: single-atom catalysts; graphitic carbon nitride; formic acid; CO2 hydrogenation; DFT References: 1. Injongkol, Y.; Intayot, R.; Yodsin, N.; Montoya, A.; Jungsuttiwong, S. Mol. Catal. 2021, 510, 111675. 2. Ma, J.; Gong, H.; Zhang, T.; Yu, H.; Zhang, R.; Liu, Z.; Yang, G.; Sun, H.; Tang, S.; Qiu, Y. Appl. Surf. Sci. 2019, 488, 1. Rattanawalee Rattanawan Ubon Ratchathani University, Thailand, B.Sc., Chemistry Ubon Ratchathani University, Thailand, M.Sc., Chemistry Ubon Ratchathani University, Thailand, Ph.D. student, Chemistry Research fields: computational and theoretical chemistry 29
P.OB-12 Natural Products from Thai medicinal plants as a valuable source of 5 alpha reductase inhibitors for the development of innovative hair growth control products Nutchaninad Tanuphol, a Kamonlak Insumrong, b Nungruthai Suphrom, b Prapapan Temkitthawon, a Nitra Nuengchamnong, c Andy Zedet, d Francois Senejoux, d Corine Girard, d and Kornkanok Ingkaninana aCenter of Excellence in Cannabis Research, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University, Phitsanulok 65000, Thailand. bDepartment of Chemistry, Faculty of Science, Naresuan University, Phitsanulok 65000, Thailand. cScience Laboratory Centre, Faculty of Science, Naresuan University, Phitsanulok 65000, Thailand. dUniversité de Franche-Comté, PEPITE, 19 rue Ambroise Paré-25000 Besançon, France. [email protected] Androgenic alopecia (AGA) or male pattern baldness is characterized by the pattern of hair loss at the scalp. It is an undesirable personality that influences stress on the patients (1). AGA is related to excessive dihydrotestosterone (DHT), a potent androgen hormone transformed from testosterone by the enzyme steroid 5 alpha-reductase (S5AR). The teak leaf extract was demonstrated to have S5AR inhibitory activity and biological activities related to hair regrowth activity (2), therefore, this extract is interesting to develop as a hair growth product. However, teak leaves harvested from different sources show inconsistency in S5AR inhibitory activity. Therefore, the purposes of this study were to determine the factors affecting S5AR inhibitory activity and chemical components and to identify the S5AR inhibitors using the metabolomic approach. The samples were divided into young and mature leaves and harvested every 3 months for 1 year. Dried leaves were extracted with ethanol. The extracts were explored on S5AR inhibitory activity parallel with chemical profiles by the LC-MS. The resulting Principal Component Analysis (PCA) indicated no differences in terms of chemical constituents between leaf ages and harvesting times. Interestingly, the sources of leaves had a significant effect on the S5AR inhibitory activity. The S-plot of Orthogonal Partial Least Squares (OPLS) navigated to some bioactive compounds which were isolated, identified, and proved to have high S5AR inhibitory activity including (+)-eperua-7,13-dien-15-oic acid (IC50 = 14.65 ± 0.31 µM) (3), hydroxysesamone (IC50 = 127.23 ± 0.81 µM) and rhinocerotinoic acid (70.45 ± 1.38% at final concentration 5 µM). This information will be useful for quality control of hair growth products containing teak leaf extract. Keywords: Tectona grandis L.; teak leaf; steroid 5-alpha reductase, Androgenic alopecia References: 1. Cash, T. The psychosocial consequences of androgenetic alopecia: a review of the research literature. Br. J. Dermatol. 1999, 141, 398. 2. Fachrunniza, Y.; Srivilai, J.; Wisuitiprot, V.; Wisuitiprot, W.; Suphrom, N.; Temkitthawon, P.; et al. Tectona grandis, a potential active ingredient for hair growth promotion. Songklanakarin Journal of Science & Technology 2020, (6), 42. 3. Insumrong, K.; et al. Isolation and HPLC quantitative determination of 5α-reductase inhibitors from Tectona grandis Lf leaf extract. Molecules 2022, 27, 2893. Prapapan Temkitthawon Naresuan University, Thailand, Ph.D., Pharmacognosy Research fields: natural products 30
P.OB-13 LC‒MS based metabolomics for identification of phosphodiesterase 5 inhibitors from Eulophia and Dendrobium species Tongchai Saesong, a Pierre‒Marie Allard,b,c,d Emerson Ferreira Queiroz,b,c Laurence Marcourt,b,c Nitra Nuengchamnong,e Prapapan Temkitthawon,a Nantaka Khorana,f Jean‒Luc Wolfender, b,c and Kornkanok Ingkaninana aCenter of Excellence in Cannabis Research, Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University, Phitsanulok 65000, Thailand. bPhytochemistry and Bioactive Natural Products, School of Pharmaceutical Sciences, University of Geneva, CMU‒Rue Michel-Servet 1, 1211 Geneva, Switzerland. c Institute of Pharmaceutical Sciences of Western Switzerland, University of Geneva, CMU‒Rue Michel-Servet 1, 1211 Geneva, Switzerland. dDepartment of Biology, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland. eScience Lab Center, Faculty of Science, Naresuan University, Phitsanulok 65000, Thailand. fDivision of Pharmaceutical Sciences, School of Pharmaceutical Sciences, University of Phayao, Phayao 56000, Thailand. [email protected] Herein, we propose an LC‒HRMS based metabolomics approach to identify PDE5 inhibitors from Eulophia and Dendrobium species. For this purpose, ninety‒three extracts from ten Eulophia and thirty‒seven Dendrobium species were investigated using UHPLC‒HRMS2 and anti‒PDE5 activity of these extracts were tested in parallel. An orthogonal partial least squares discriminant analysis (OPLS‒ DA) was applied for correlating the chemical compositions of the extracts and their biological activity results to anticipate the presence of bioactive compounds. Using this model, eight phenanthrenes were highlighted to be potential bioactive markers by S‒plot and six of them (1‒6) were successfully isolated and shown to possess great anti‒PDE5 activity. Three compounds with closely related structures (1, 2 and 6), were the most active compounds. Based on the potency and high yield of 1, this compound was selected as a biomarker for quality control of some Eulophia species with PDE5 inhibitory activity such as E. macrobulbon, E. nuda and E. petersii. An LC‒MS method was developed and validated for determination of 1 and its result demonstrated high accuracy, precision, and sensitivity, which will be useful for quality control of those Eulophia samples. In addition, the structure‒activity relationship (SAR) of six isolated bioactive phenanthrenes (1‒6) and three non‒highlighted phenanthrenes (7‒9) were investigated. The SAR results allowed to propose a model for the recognition of structural requirements on the anti‒PDE5 effect. These results can serve as a guide for discovery of new drug candidates for erectile dysfunction which shows the high potency and selectivity towards the PDE5 inhibitors. Keywords: metabolomics; LC‒MS; PDE5; Eulophia; Dendrobium Tongchai Saesong Naresuan University, Thailand, B.Sc., Chemistry Naresuan University, Thailand, Ph.D., Pharmaceutical Sciences Research fields: metabolomic based LC-MS and GC-MS, natural products, phytochemical analysis, quality control 31
P.NS-01 PHOTO Height 2.5 cm Width 2.1 cm Development of antibacterial agents against global predominant methicillin-resistant Staphylococcus aureus USA300 Onanong Vorasina , Khanchyd Momphanaoa , Praewpan Katrunb , Chutima Kuhakarna , and Chutima Jiarpinitnuna aDepartment of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. bDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand. [email protected] Excessive and inappropriate uses of antibiotics give rise to the emergence of antibiotic resistance in alarming rate. Treatments of antibiotic resistant infections are complicated as finding effective antibiotics would become more challenging, leading to prolonged illness and death. Global epidemic methicillin-resistant Staphylococcus aureus (MRSA), particularly MRSA PFGE strain type USA300 (SF8300) is of interest. USA300 is known as community-acquired MRSA; its rapid transmission and resistance towards antibiotics lead to global healthcare problem. Effective antibacterial agents are called for. Our group have reported potent several antibacterial agents against MRSA USA300, including synthetically modified natural product, caged xanthones. Recently, we discovered potent synthetic small molecules from focused chemical library that were rationally designed and synthesized. The results revealed potent antibacterial vinyl sulfones with MIC of 1.875 µg/mL against methicillin-susceptible S. aureus ATCC 29213 and 3.75 µg/mL against methicillinresistant S. aureus USA300. Our study suggested that these vinyl sulfones could rapidly undergo thiolMichael addition under physiological condition with bacterial cysteine-containing proteins. In S. aureus and MRSA, cysteine proteinases play vital roles in bacterial survival and pathogenesis; therefore, these vinyl sulfones have potential to interfere with S. aureus survival and virulence. We further investigated the abilities of of these vinyl sulfones to inhibit catalytic activity of S. aureus cysteine transpeptidase SrtA and to interfere with SrtA-mediated S. aureus adhesion to fibronectin. The results revealed that nitrile substituted vinyl sulfone could exert highly potent SrtA inhibitory activity, significantly more potent than previously reported non-substituted PVS, leading to the impair of host cell adhesion. With their promising antibacterial activities, these vinyl sulfones have potential for S. aureus and MRSA therapeutics. Keywords: MRSA USA300; antibacterial agents; vinyl sulfones References: 1. Vorasin, O.; Momphanao, K.; Katrun, P.; Kuhakarn, C.; Jiarpinitnun, C. Bioorg. Chem. Lett. 2022, 63, 128652. 2. Chaiyakunvat, P.; Anantachoke, N.; Reutrakul, V.; Jiarpinitnun, C. Bioorg. Chem. Lett. 2016, 63, 2980-2983. Chutima Jiarpinitnun The University of Chicago, USA, B.Sc., Chemistry University of Wisconsin-Madison, USA, Ph.D., Chemistry Research fields: bioorganic chemistry, chemical biology, organic chemistry 32
P.NS-02 PHOTO Height 2.5 cm Width 2.1 cm Discovery of andrographolide analogues as novel inhibitor targeting SARS-COV-2 main protease: in vitro and in silico study Bodee Nuthoa , Patcharin Wilasluckb , Peerapon Deetanyab , Kittikhun Wangkanontb , Patcharee Arsakhantc , Rungnapha Saeengc , and Thanyada Rungrotmongkold aDepartment of Pharmacology, Faculty of Science, Mahidol University, Bangkok 10400, Thailand. bCenter of Excellence for Molecular Biology and Genomics of Shrimp, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. cDepartment of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand. dCenter of Excellence in Biocatalyst and Sustainable Biotechnology, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. [email protected] The discovery of antiviral agent is frontier research in the fight against COVID-19 caused by SARS-CoV-2 infection. To date, a modified compound derived from natural products is of particular interest for the drug discovery pipeline. One of the most promising drug targets for COVID-19 therapy is the viral main protease (Mpro), which plays a pivotal role in viral life cycle and replication. Herein, a series of twenty-one 12-dithiocarbamate-14-deoxyandrographolide analogues was explored for their anti-SARS-CoV-2 Mpro potential utilizing in vitro and in silico studies. Initially, we screened the inhibitory effect of these compounds on SARS-CoV-2 Mpro using in vitro enzyme inhibition assay. The results showed that there were four promising candidates, namely 3k, 3l, 3m and 3t that exhibited the inhibitory activity against Mpro with >50% inhibition at 10 μM. In silico molecular docking was conducted to determine the optimum binding mode of each focused compound in the enzyme active site and then subjected to molecular dynamics (MD) simulations. The MD results revealed that all studied complexes were relatively stable during MD simulation, and most of the compounds could specifically bind to the SARS-CoV-2 Mpro active site, especially at S1, S2 and S4 subsites. The hot-spot residues essential for ligand binding were T25, H41, C44, S46, M49, C145, H163, M165, E166, L167, D187, R188, Q189 and T190. Therefore, our findings from combined experimental and computational approaches could be useful for further design of more potent compounds targeting SARS-CoV-2 Mpro . Keywords: andrographolide analogues; computational study; COVID-19; drug discovery; enzymebased assay References: 1. Nutho, B.; Wilasluck, P.; Deetanya, P.; Wangkanont, K.; Arsakhant, P.; Saeeng, R.; Rungrotmongkol, T. Comput. Struct. Biotechnol. J. 2022, 20, 2784–2797. Bodee Nutho Chulalongkorn University, Thailand, B.Sc., Biochemistry Mahidol University, Thailand, M.Sc., Pharmacology Chulalongkorn University, Thailand, Ph.D., Biotechnology Research fields: computer-aided drug design and discovery, MD simulation of biomolecules 33
P.NS-03 PHOTO Height 2.5 cm Width 2.1 cm The anti-cancer activity of natural products from Mallotus spodocarpus in cholangiocarcinoma Wittaya Panvongsa, a Thanwarat Winitchaikul, b Phaewa Chaiwijit, b Prapadsorn Pittayanurak, c Natthapat Sawektreeratana,c Chutima Kuhakarn, c Vichai Reutrakul, c Sakchai Hongthong,d and Arthit Chairoungduab aDepartment of Tropical Nutrition and Food Science, Faculty of Tropical Medicine, Mahidol University, Ratchawithi Rd, Bangkok 10400, Thailand. bDepartment of Physiology, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. cDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Bangkok 10400, Thailand. dDivision of Chemistry, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand. [email protected] Cholangiocarcinoma (CCA) is a highly aggressive cancer that arises from the biliary epithelial cells, with a higher incidence and mortality rate. The prognosis for CCA is poor, with a 5-year overall survival (OS) rate of 7–20% and a median OS of less than 12 months1 . Lack of responsiveness to pharmacological therapy represents a significant limitation in managing CCA patients. Therefore, investigating novel anticancer therapeutics to overcome this limitation is urgently needed. In this study, we evaluated the anticancer activities of a compound (VR27009) isolated from Mallotus spodocarpus in two CCA cell lines, KKU-M213 and KKU-M055, compared with normal human cholangiocyte cell lines MNNK-1. VR27009 exhibited a potent cytotoxic effect in KKU-M213, KKU-M055, and MNNK1 and was more potent than 5-FU at all time points. However, CCA cells were more sensitive than MNNK-1 cells indicating the potential to develop VR27009 as an anticancer agent for CCA treatment. At 24 h, treatment with VR27009 at a concentration of 0.01 µM significantly suppressed BrdU incorporation and increased cell cycle distribution at G0/G1 phase in both CCA cell lines. Moreover, apoptosis death was induced by treatment VR27009 only at the higher concentration, suggesting the cytostatic effect on CCA cells at lower concentrations and cytotoxic effect at higher concentrations. Protein expression profiles showed that 190 and 159 proteins significantly increased and decreased in VR27009-treated KKU-M055 cells compared to untreated cells. Interestingly, signaling pathways related to protein translation and tRNA aminoacylation were most predicted considerably. Based on the results, we suggest that VR27009 exhibited anticancer activity against CCA partly by interfering with protein synthesis through the protein translation processes. Keywords: cholangiocarcinoma; anticancer; M. spodocarpus; cytostatic; cytotoxic References: 1. Banales, J.M.; Marin, J.J.G.; Lamarca, A.; Rodrigues, P.M.; Khan, S.A.; Roberts, L.R.; et al. Nat. Rev. Gastroenterol. Hepatol. 2020, 17, 557-588. Wittaya Panvongsa Kasetsart University, Thailand, B.Sc., Biology Mahidol University, Thailand, M.Sc., Toxicology Mahidol University, Thailand, Ph.D., Toxicology Research fields: drug discovery, extracellular vesicles, cancer biomarker 34
P.NS-04 PHOTO Height 2.5 cm Width 2.1 cm Cyclic peptide VR27009 inhibits proliferation, migration and invasion of HCT116 and MDA-MB-231 cancer cells through down-regulation of key lipogenic enzymes Chayanee Laowittawat, a,b Kanlaya Katewongsa,b Prapadsorn Pittayanurak, c Natthapat Sawektreeratana,c Chutima Kuhakarn, c Vichai Reutrakul,c Sakchai Hongthong,d and Sarawut Jitrapakdee, b aGraduate Program in Molecular Medicine, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. bDepartment of Biochemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. cDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. dDivision of Chemistry, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand. [email protected] The cyclic peptides are naturally present in several organisms such as plants, marine organisms and animals. VR27009 has recently been isolated from Mallotus spodocarpus root extract. However, the molecular mechanism underlying its anti-cancer activity have not been investigated. According to high cell growth and proliferation rate, cancer cell provide energy for supporting cell growth via metabolic reprogramming. Furthermore, cancer cells require more on de novo lipogenesis for promote cancer cell proliferation and metastasis. Thus, inhibition of de novo lipogenesis in cancer can disturb cancers proliferation and metastasis. Therefore, the present study aims to examine the anti-cancer activity of VR2700 though de novo lipogenesis. Anti-cancer activity was determined by using MTT clonogenic and trans-well assays. MTT and clonogenic assays showed that VR27009 inhibited cancer growth at the inhibitory concentration 50% (IC50) of 0.1 nM following 48 h exposure to MDA-MB-231 (breast cancer) and HCT116 (colon cancer) cells. Trans-well assay showed that VR27009 suppresses cell migration and invasion of both cell lines as a dose-dependent manner. The IC50 of VR27009 required to suppress cellular migration and invasion for MDA-MB-231 and HCT116 was 1.0 nM and 0.1 nM, respectively. Western blot analysis of both cell lines exposing to VR27009 for 48 h inhibited the expression of acetyl-CoA carboxylase-1 (ACC1) and fatty acid synthase (FASN), the two key regulatory enzymes of lipogenesis by 50%. However, VR27009 did not affect the expression of the key enzyme of cholesterol synthesis enzyme, i.e. HMG-CoA reductase, suggesting that this compound interferes fatty acid biosynthesis rather than cholesterol. The present finding suggests that VR27009 may be potential candidate to further develop a new drug treatment for cancer. Keywords: cancer; Mallotus spodocarpus; lipid metabolism References: 1. Zhang, F.; Du, G. World J. Biol. Chem. 2012, 3, 167-174. 2. Moustafa, G. Egypt. J. Chem. 2021, 64, 1777-1787. Chayanee Laowittawat Khon Kaen University, Bangkok, B.Sc., Biology Mahidol University, Bangkok, M. Sc., Pharmacology Mahidol University, Bangkok, Ph.D. candidate, Molecular Medicine Research fields: cancer metabolism 35
P.NS-05 Development of ZY-444-loaded PLGA-nanoparticles for targeting cancer cells Siraprapa Siritutsootorn, a Kanlaya Katewongsa,a Natthapat Sawekteeratana, b Chutima Kuhakarn, b and Sarawut Jitrapakdeea aDepartment of Biochemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. bDepartment of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand. [email protected] Pyruvate carboxylase (PC) is an important anaplerotic enzyme that replenishes the tricarboxylic acid cycle intermediates removed for the synthesis of macromolecules such as nucleic acids, amino acids, and lipids. Genetic suppression of the PC gene inhibited the growth of many cancers [1-2]. Compound (N4-((5-(4-(benzyloxy)phenyl)-2-thiophenyl)methyl)-N2-isobutyl-2,4-pyrimidine-diamine (ZY-444: molecular weight 444 kDa) has recently been reported to possess an anti-cancer activity in vitro and in vivo through inhibiting PC activity [3]. ZY-444 inhibits growth of several cancer cell lines such as breast cancer, colon cancer, and lung cancers at sub-micromolar concentrations, with breast cancer cell lines being most sensitive to this compound. Remarkably, this compound inhibits growth of breast cancer cells with low IC50 comparing with a widely used paclitaxel anti-cancer drug. Although this compound specifically inhibits growth of cancer cells bearing high PC activity, some other normal tissues that possess high PC activity such as liver and adipose tissue are likely to be affected by this compound. We propose to specifically target this compound by encapsulating it with the organic nanopolymer, PLGA with its surface modified with cancer-specific ligand, riboflavin transporters (RFVTs). These transporters were overexpressed in many types of cancers thus providing an ideal choice for the ligand-specific delivery system for cancer cells. In this study, ZY-444-loaded PLGA nanoparticles coated with riboflavin (Rf)-functionalized chitosan (CSRf) were developed using solvent emulsion evaporation methods. PLGA-CSRf-ZY-444 nanoparticles effectively reduced the growth of both colon (HCT-116) and breast (MDA-MB-231) cancer cells while this growth inhibition was not observed with cancer cells exposed to unencapsulated PLGA. This study highlights the application of ZY-444-loaded nanoparticles as the delivery route to both colon and breast cancer cells. Keywords: cancer metabolism; pyruvate carboxylase; ZY-444; nanoparticles References: 1. Phannasil, P.; Thuwajit, C.; Warnnissorn, M.; Wallace, J. C.; MacDonald, M. J.; Jitrapakdee, S. PLoS One 2015, 10 (6), 1-20. 2. Ngamkham, J.; Siritutsoontorn, S.; Saisomboon, S.; Vaeteewoottacharn, K.; Jitrapakdee, S. Front. Oncol. 2022, 12, 1-14. 3. Lin, Q.; He, Y.; Wang, X.; Zhang, Y.; Hu, M.; Guo, W.; He, Y.; Zhang, T.; Lai, L.; Sun, Z.; Yi, Z.; Liu, M.; Chen, Y. Adv. Sci. 2020, 7(9), 1-15. Siraprapa Siritutsoontorn Kasetsart University, Thailand, B.Sc., Biology Mahidol University, Thailand, M.Sc., Biochemistry Mahidol University, Thailand, Ph.D. candidate, Biochemistry Research fields: biology, biochemistry 36
2023 Thailand - Taiwan Bilateral Symposium July 23 - 26, 2023, Classic Kameo Hotel Serviced Apartment, Ayutthaya, THAILAND IL.OB-01 Assoc. Prof. Sakda Khoomrung Faculty of Medicine Siriraj Hospital, Mahidol University Thailand [email protected] IL.OB-02 Prof. Ru-Shi Liu Department of Chemistry, National Taiwan University Taiwan [email protected] IL.OB-03 Dr. Kaito Takahashi Institute of Atomic and Molecular Sciences, Academia Sinica Taiwan [email protected] IL.OB-04 Prof. Siriporn Jungsuttiwong Faculty of Science, Ubon Ratchathani University Thailand [email protected] IL.OB-05 Assoc. Prof. Ho-Hsiu Chou Department of Chemical Engineering, National Tsing Hua University Taiwan [email protected] IL.OB-06 Dr. Hsien-Ming Lee Institute of Chemistry, Academia Sinica Taiwan [email protected] IL.OB-07 Assoc. Prof. Ekasith Somsook Faculty of Science, Mahidol University Thailand [email protected] IL.OB-08 Dr. Pinit Kidkhunthod Synchrotron Light Research Institute Thailand [email protected] P.OB-01 Assoc. Prof. Jonggol Tantirungrotechai Faculty of Science, Mahidol University Thailand [email protected] P.OB-02 Dr. Nolan Betterley Faculty of Science, Mahidol University Thailand [email protected] P.OB-03 Dr. Sariyarach Thanasansurapong Faculty of Pharmaceutical Sciences, Chulalongkorn University Thailand [email protected] P.OB-04 Dr. Thitaree Pimklang Faculty of Science, Mahidol University Thailand [email protected] P.OB-05 Mr. Manopat Depijan Faculty of Science, Mahidol University Thailand [email protected] P.OB-06 Mr. Farman Ali Faculty of Science, Mahidol University Pakistan [email protected] P.OB-07 Mr. Thinnaphat Poonsawat Faculty of Science, Mahidol University Thailand [email protected] P.OB-08 Mr. Peerapong Promcharoen Faculty of Science, Mahidol University Thailand [email protected] P.OB-09 Mrs. Kaleeswari Kalimuthu Faculty of Science, Mahidol University India [email protected] P.OB-10 Dr. Narumol Jariyasopit Faculty of Medicine Siriraj Hospital, Mahidol University Thailand [email protected] P.OB-11 Dr. Rattanawalee Rattanawan Faculty of Science, Ubon Ratchathani University Thailand [email protected] P.OB-12 Asst. Prof. Prapapan Temkittawon Faculty of Pharmaceutical Sciences, Naresuan University Thailand [email protected] P.OB-13 Dr. Tongchai Saesong Faculty of Pharmaceutical Sciences, Naresuan University Thailand [email protected] PP.OB-01 Prof. Vichai Reutrakul Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-02 Assoc. Prof. Pasit Pakawatpanurut Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-03 Dr. Narong Nuntasaen Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-04 Prof. Apichart Suksamrarn Center of Excellence for Innovation in Chemistry, Ramkhamhaeng University Thailand [email protected] PP.OB-05 Prof. Vatcharin Rukachaisirikul Center of Excellence for Innovation in Chemistry, Prince of Songkla University Thailand [email protected] PP.OB-06 Prof. Yu-Ju Chen Institute of Chemistry, Academia Sinica Taiwan yujuchengate.sinica.edu.tw PP.OB-07 Prof. Po-Chiao Lin Department of Chemistry, National Sun Yat-sen University Taiwan [email protected] PP.OB-08 Mr. Tanawut Meekati Faculty of Science, Mahidol University Thailand [email protected] PP.OB-09 Dr. Thaworn Jaipetch Faculty of Science, Mahidol University Thailand [email protected] PP.OB-10 Miss Prapadsorn Pittayanurak Faculty of Science, Mahidol University Thailand [email protected] PP.OB-11 Miss Samreang Bunteang Faculty of Science, Mahidol University Thailand [email protected] PP.OB-12 Miss Amporn Saekee Faculty of Science, Mahidol University Thailand [email protected] PP.OB-13 Miss Kannika La-ongthong Faculty of Science, Mahidol University Thailand [email protected] PP.OB-14 Miss Jongkonporn Phetcharawetch Faculty of Science, Mahidol University Thailand [email protected] PP.OB-15 Dr. Pattipong Wisanpitayakorn Faculty of Medicine Siriraj Hospital, Mahidol University Thailand [email protected] PP.OB-16 Mr. Ammarin In-on Faculty of Medicine Siriraj Hospital, Mahidol University Thailand [email protected] PP.OB-17 Dr. Kwanjeera Wanichthanarak Faculty of Medicine Siriraj Hospital, Mahidol University Thailand [email protected] PP.OB-18 Miss Suphitcha Limjiasahapong Faculty of Medicine Siriraj Hospital, Mahidol University Thailand [email protected] PP.OB-19 Assoc. Prof. Pakorn Wattana-amorn Faculty of Science, Kasetsart University Thailand [email protected] PP.OB-20 Assoc. Prof. Pitak Chuawong Faculty of Science, Kasetsart University Thailand [email protected] PP.OB-21 Prof. Sutisa Thanoi Faculty of Medical Science, Naresuan University Thailand [email protected] PP.OB-22 Miss Phichsinee Rerkshanandana Faculty of Pharmaceutical Sciences, Naresuan University Thailand [email protected] PP.OB-23 Assoc. Prof. Sila Kittiwachana Faculty of Science, Chiang Mai University Thailand [email protected] PP.OB-24 Assoc. Prof. Boon-ek Yingyongnarongkul Faculty of Science, Ramkhamhaeng University Thailand [email protected] PP.OB-25 Mrs. Pongsri Katepongchai Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-26 Miss Patcharee Duang-ngoen Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-27 Mr. Kritchawat Chomchuenjit Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-28 Miss Yaowarat Plengsangsri Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.OB-29 Miss Natthamon Chaiyaboon Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] INVITED LECTURE POSTER PRESENTATION PARTICIPANTS 37
2023 Thailand - Taiwan Bilateral Symposium July 23 - 26, 2023, Classic Kameo Hotel Serviced Apartment, Ayutthaya, THAILAND IL.NS-01 Prof. Jang-Yang Chang Taipei Cancer Center, Taipei Medical University Taiwan [email protected] IL.NS-02 Prof. Hsing-Pang Hsieh Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes Taiwan [email protected] IL.NS-03 Prof. Sarawut Jitrapakdee Faculty of Science, Mahidol University Thailand [email protected] IL.NS-04 Assoc. Prof. Kanlaya Katewongsa Faculty of Science, Mahidol University Thailand [email protected] IL.NS-05 Assoc. Prof. Arthit Chairoungdua Faculty of Science, Mahidol University Thailand [email protected] IL.NS-06 Prof. Hsyueh-Liang Wu Department of Chemistry, National Taiwan Normal University Taiwan [email protected] IL.NS-07 Prof. Chutima Kuhakarn Faculty of Science, Mahidol University Thailand [email protected] P.NS-01 Asst. Prof. Chutima Jiarpinitnun Faculty of Science, Mahidol University Thailand [email protected] P.NS-02 Asst. Prof. Bodee Nutho Faculty of Science, Mahidol University Thailand [email protected] P.NS-03 Dr. Wittaya Panvongsa Department of Tropical Nutrition and Food Science Faculty of Tropical Medicine, Mahidol University Thailand [email protected] P.NS-04 Miss Chayanee Laowittawat Faculty of Science, Mahidol University Thailand [email protected] P.NS-05 Miss Siraprapa Siritutsoontorn Faculty of Science, Mahidol University Thailand [email protected] PP.NS-01 Dr. Sakchai Hongthong Faculty of Science and Technology, Rajabhat Rajanagarindra University Thailand [email protected] PP.NS-02 Dr. Nolan Betterley Faculty of Science, Mahidol University Thailand [email protected] PP.NS-03 Miss Natthapat Sawekteeratana Faculty of Science, Mahidol University Thailand [email protected] PP.NS-04 Miss Thanwarat Winitchaikul Faculty of Science, Mahidol University Thailand [email protected] PP.NS-05 Miss Preeyanuch Manohong Faculty of Science, Mahidol University Thailand [email protected] PP.NS-06 Miss Atcharawadee Thanomlek Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.NS-07 Miss Boontarika Singjun Center of Excellence for Innovation in Chemistry, Mahidol University Thailand [email protected] PP.NS-08 Mr. Nattawoot Hassa Faculty of Science, Mahidol University Thailand [email protected] PP.NS-09 Mr. Thanathip Chomphunuch Faculty of Science, Mahidol University Thailand [email protected] INVITED LECTURE POSTER PRESENTATION PARTICIPANTS 38