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Biological Evaluation of Sulfonate and Sulfate Analogues of Lithocholic Acid: A Bioisosterism-Guided Approach Towards the discovery of Potential Sialyltransferase Inhibitors for Antimetastatic Study

SSRN

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SSRN 2023年

作者： Perez, Ser John Lynon P. Chen, Chia-Ling Chang, Tzu-Ting Li, Wen-Shan Institute of Chemistry Academia Sinica Taipei115 Taiwan Department of Applied Chemistry National Yang Ming Chiao Tung University Hsinchu300 Taiwan Sustainable Chemical Science and Technology Taiwan International Graduate Program Academia Sinica Taipei115 Taiwan Biomedical Translation Research Center Academia Sinica Taipei115 Taiwan Department of Medicinal and Applied Chemistry College of Life Science Kaohsiung Medical University Kaohsiung807 Taiwan Ph.D. Program in Drug Discovery and Development Industry College of Pharmacy Taipei Medical University Taiwan Doctoral Degree Program in Marine Biotechnology National Sun Yat-Sen University Kaohsiung804 Taiwan Department of Chemistry College of Science Tamkang University New Taipei City251 Taiwan

The naturally occurring bile acid lithocholic acid (LCA) has been a crucial core structure for many non-sugar-containing sialyltranferase (ST) inhibitors documented in literature. With the aim of elucidating the impact of the terminal carboxyl acid substituent of LCA on its ST inhibition, in this present study, we report the (bio)isosteric replacement-based design and synthesis of sulfonate and sulfate analogues of LCA. Among these compounds, the sulfate analogue SPP-002 was found to selectively inhibit N-glycan sialylation by at least an order of magnitude, indicating a substantial improvement in both potency and selectivity when compared to the unmodified parent bile acid. Molecular docking analysis supported the stronger binding of the synthetic analogue in the enzyme active site. Treatment with SPP-002 also hampered the migration, adhesion, and invasion of MdA-MB-231 cells in vitro by suppressing the expression of signaling proteins involved in the cancer metastasis-associated FAK/paxillin pathway. In totality, these findings offer not only a novel structural scaffold but also valuable insights for the future development of more potent and selective ST inhibitors with potential therapeutic effects against tumor cancer metastasis. © 2023, The Authors. All rights reserved.

关键词： Sulfur compounds

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diterpenoids and Their Glycosides from the Stems ofTinospora crispawith Beta-Cell Protective Activity

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Journal of Natural Products 2023年第6期86卷 1437-1448页

作者： Sio-Hong Lam Hui-Kang Liu Shih-Yuan Chung Jia-Ling Chang Mao-Xuan Hong Sheng-Chu Kuo Chih-Chuang Liaw School of Pharmacy College of Medicine National Cheng Kung University Tainan 70101 Taiwan Division of Basic Chinese Medicine National Research Institute of Chinese Medicine Ministry of Health and Welfare Taipei 112 Taiwan Ph.D. Program in the Clinical Drug Development of Herbal Medicine Taipei Medical University Taipei 11031 Taiwan Graduate Institute of Pharmaceutical Chemistry China Medical University Taichung 404 Taiwan Department of Marine Biotechnology and Resource National Sun Yat-sen University Kaohsiung 80424 Taiwan Department of Science Application and Dissemination National Taichung University of Education Taichung 403 Taiwan Graduate Institute of Natural Products Kaohsiung Medical University Kaohsiung 807 Taiwan Graduate Institute of Pharmacognosy Taipei Medical University Taipei 11031 Taiwan

Seven previously undescribed diterpenoids, tinocrisposides A–d (1–4) and borapetic acids A (5), B (6), and C (7), together with 16 known compounds, were isolated from the stem ofTinospora crispa(Menispermaceae). The structures of the new isolates were elucidated by spectroscopic and chemical methods. The β-cell protective effect of the tested compounds was examined on insulin-secreting BRIN-Bd11 cells under dexamethasone treatment. diterpene glycosides12,14–16, and18presented a substantial protective effect on BRIN-Bd11 cells treated with dexamethasone in a dose-dependent manner. Compounds4and17with two sugar moieties exhibited clear protective effects on β-cells.

关键词： Alkyls Carbohydrates Carbon Chemical structure Nuclear magnetic resonance spectroscopy

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16-IN GUN BLAST ANd THE BATTLESHIP REACTIVATION program

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NAVAL ENGINEERS JOURNAL 1987年第3期99卷 227-238页

作者： YAGLA, JJ The authorreceived his B. A. degree in science (physics) from the State College of Iowa in 1965. He received his M. S. degree in engineering mechanics in 1968 and his Ph.D in aerospace engineering and engineering science in 1981 from Arizona State University. He has done analytical and experimental research in the field of weapons blast since 1965 at the Naval Surface Weapons Center in Dahlgren Virginia. As a supervisory research mechanical engineer he was previously head of the Physical Response Analysis Branch Blast Effects Branch and Ship Engineering Branch. Dr. Yagla is the test development agent and was test conductor for the gun and missile structural test firings in USS Iowa class battleships. He is a consultant to the Naval Sea Systems Command battleship combat system engineer and the Naval Air Systems Command Cruise Missile Project for blast and structural response. He is presently analyzing shock and vibration problems for the Standard Missile Program Office.

Reactivated and modernized USS Iowa class battleships employ many new systems, none of which were designed to withstand blast from 16-inch guns. Placement of the new equipment was driven by the need to impose the smallest possible restrictions on the guns. The design problem was complicated by two factors: first, the blast overpressure field surrounding the gun had not been accurately measured with modern instruments. Second, the blast overpressure tolerance of several important systems was unknown. The problem was solved through judicious placement of the equipment so that work could begin on the ship. Meanwhile the pressure surrounding a 16-inch gun was measured at the dahlgren Laboratory. Mathematical functions describing the blast field were then used to design shipboard experiments in which the guns were fired at progressively more severe angles of train and elevation, while the equipment performance was carefully monitored. Four sets of shipboard experiments were required. Limiting values for the firing arcs have been determined, and the consequences of exceeding the recommended limits are now known.

关键词： WARSHIPS

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Overall mortality risk analysis for rectal cancer using deep learning-based fuzzy systems

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Computers in Biology and Medicine 2023年 157卷 106706-106706页

作者： Yang, Cheng-Hong Chen, Wen-Ching Chen, Jin-Bor Huang, Hsiu-Chen Chuang, Li-Yeh Department of Information Management Tainan University of Technology Tainan Taiwan Department of Electronic Engineering National Kaohsiung University of Science and Technology Kaohsiung Taiwan Ph. D. Program in Biomedical Engineering Kaohsiung Medical University Kaohsiung Taiwan School of Dentistry Kaohsiung Medical University Kaohsiung Taiwan Drug Development and Value Creation Research Center Kaohsiung Medical University Kaohsiung Taiwan Department of Internal Medicine Kaohsiung Chang Gung Memorial Hospital and Chang Gung University College of Medicine Kaohsiung Taiwan Department of Community Health Chia-Yi Christian Hospital Chia-Yi City Taiwan Department of Chemical Engineering & Institute of Biotechnology and Chemical Engineering I-Shou University Kaohsiung Taiwan

Colorectal cancer is a leading cause of cancer mortality worldwide, with an increasing incidence rate in developing countries. Integration of genetic information with cancer therapy guidance has shown promise in cancer treatment, indicating its potential as an essential tool in translation oncology. However, the high-throughput analysis and variability of genomic data poses a major challenge to conventional analytic approaches. In this study, we propose an advanced analytic approach, named "Fuzzy-based RNNCoxph," incorporated fuzzy logic, recurrent neural networks (RNNs), and Cox proportional hazards regression (Coxph) for detecting missense variants associated with high-risk of all-cause mortality in rectum adenocarcinoma. The test data set was downloaded from "Rectum adenocarcinoma, TCGA-REAd" the Genomic data Commons (GdC) portal. In this study, four model-based risk score models were derived using RNN, Coxph, RNNCoxph.ddition, and RNNCoxphMultiplication. The RNNCoxph.ddition and RNNCoxphMultiplication models were obtained as the sum and product of the RNN risk degree matrix and the Coxph risk degree matrix, respectively. Moreover, the fuzzy logic system was used to calculate the survival risk values of missense variants and classified their membership grade to improve the identification of high-risk gene variation locations associated with cancer mortality. The four models were integrated to develop an advanced risk estimation model. There were 20 028 variants associated with survival status, amongst 17 638 variants were associated with survival and 2390 variants associated with mortality. The proposed Fuzzy-based RNNCoxph model obtained a balanced accuracy of 93.7%, which was significantly higher than that of the other four test methods. In particular, the Coxph model is commonly used in medical researches and the XGBoost model is famous for its high accuracy in machine learning. The results suggest that the Fuzzy-based RNNCoxph model exhibits a higher efficacy

关键词： Fuzzy logic

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Nucleocytoplasmic shuttling of BEFV M protein-modulated by lamin A/C and chromosome maintenance region 1 through a transcription-, carrier- and energy-dependent pathway

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Veterinary Microbiology 2024年 291卷 110026页

作者： Chang, Yu-Kang Lin, Yi-Jyum Cheng, Ching-Yuan Tsai, Pei-Chien Wang, Chi-Young Nielsen, Brent L. Liu, Hung-Jen Department of Medical Research Tungs’ Taichung MetroHarbor Hospital Taichung Taiwan Depertment of Post-Baccalaureate Medicine National Chung Hsing University Taichung Taiwan Institute of Molecular Biology National Chung Hsing University Taichung 402 Taiwan Department of Life Sciences National Chung Hsing University Taichung Taiwan Department of Veterinary Medicine National Chung Hsing University Taichung 402 Taiwan The iEGG and Animal Biotechnology Center National Chung Hsing University Taichung Taiwan Department of Microbiology and Molecular Biology Brigham Young University Provo UT United States Ph.D Program in Translational Medicine National Chung Hsing University Taichung Taiwan Rong Hsing Research Center for Translational Medicine National Chung Hsing Taiwan

This study demonstrates for the first time that the matrix (M) protein of BEFV is a nuclear targeting protein that shuttles between the nucleus and the cytoplasm in a transcription-, carrier-, and energy-dependent manner. Experiments performed in both intact cells and digitonin-permeabilized cells revealed that M protein targets the nucleolus and requires carrier, cytosolic factors or energy input. By employing sequence and mutagenesis analyses, we have determined both nuclear localization signal (NLS) ⁶KKGKSK¹¹ and nuclear export signal (NES) ⁹⁸LIITSYL TI¹⁰⁶ of M protein that are important for the nucleocytoplasmic shuttling of M protein. Furthermore, we found that both lamin A/C and chromosome maintenance region 1 (CRM-1) proteins could be coimmunoprecipitated and colocalized with the BEFV M protein. Knockdown of lamin A/C by shRNA and inhibition of CRM-1 by leptomycin B significantly reduced virus yield. Collectively, this study provides novel insights into nucleocytoplasmic shuttling of the BEFV M protein modulated by lamin A/C and CRM-1 and by a transcription- and carrier- and energy-dependent pathway. © 2024 Elsevier B.V.

关键词： Bovine ephemeral fever virus CRM-1 Lamin A/C Matrix (M) protein Nuclear export signal (NES) Nuclear localization signal (NLS)

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Polymethoxyflavone from Citrus depressa as an inhibitor against various variants of SARS-CoV-2 spike protein

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Journal of Ethnopharmacology 2024年 320卷 117412页

作者： Liu, Ta-Wei Hsu, Su-Jung Hsieh, Yves S.Y. Liu, Hui-Kang Lee, Ching-Kuo School of Pharmacy College of Pharmacy Taipei Medical University Taipei 11042 Taiwan Graduate Institute of Pharmacognosy College of Pharmacy Taipei Medical University Taipei 11042 Taiwan Division of Glycoscience Department of Chemistry School of Engineering Sciences in Chemistry Biotechnology and Health KTH Royal Institute of Technology AlbaNova University Centre Stockholm SE106 91 Sweden National Research Institute of Chinese Medicine (NRICM) Ministry of Health and Welfare Taipei City Taiwan Ph. D. Program in the Clinical Drug Development of Herbal Medicine Taipei Medical University Taipei Taiwan

Ethnopharmacological relevance: In traditional Taiwanese medicine, Citrus depressa Hayata serves as the raw material of Chen-Pi which has been widely used to treat respiratory ailments. Scientific investigations have validated the attributes of C. depressa, elucidating its valuable properties, including antioxidative, anti-inflammatory, anticancer, neuroprotion, hepatoprotection, and hypolipidemic effects. Aim of the study: This study aims to isolate a universal inhibitor of the SARS-CoV-2 spike protein from C. depressa and confirm the mechanism by which these inhibitors disrupt the binding of the spike protein to hACE2. Materials and methods: The whole fruit of C. depressa was subjected to ethanol extraction, following by partitioning to obtain water, butanol, and ethyl acetate fractions. To identify the inhibitory components in citrus fruits, we performed both the SPR assay and the SARS-CoV-2 pseudo-virus assays. Subsequently, we employed a bioassay-guided approach to efficiently isolate and characterize the bioactive constituents that hindered the interaction between the SARS-CoV-2 spike protein and hACE2, using a combination of MPLC and Semi-preparative HPLC for compound isolation. ELISA based spike protein binding assay evaluate the inhibitory activities of the extract and potential constituents against multiple spike protein variants. To further shed light on the inhibitory mechanism, candidate inhibitors were validated through the SPR assay and molecular docking. Results: The crude extract and ethyl acetate layer derived from C. depressa showed significant inhibitory activity on SARS-CoV-2 Omicron BA.4/5, with IC₅₀ of 77.4 μg/mL and 100 μg/mL, respectively. Ten potential compounds from C. depressa have been identified with inhibitory activity against various SARS-CoV-2 spike proteins. 2′-hydroxy-4,4′,5′,6′-tetramethoxychalcone (Cd3) and 5-hydroxy-3′,4′,6,7,8-pentamethoxyflavone (Cd8) also showed good inhibitory activity to the spike protein, with K

关键词： ACE-2 Citrus depress Polymethoxyflavone SARS-CoV-2 Spike protein

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CHEMICAL MASS-BALANCE APPROACH TO FIELd-EVALUATION OF BIOREMEdIATION

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ENVIRONMENTAL PROGRESS 1995年第1期14卷 F2-F3页

作者： SIMS, RC SIMS, JL Utah State University Department of Civil and Environmental Engineering and Utah Water Research Laboratory Logan UT 84322 Professor and Head of the Division of Environmental Engineering at Utah State University. He holds degrees in biology (B.S.) environmental chemistry and biology (M.S.) environmental engineering (M.S.) and biological and agricultural engineering (Ph.D). He has worked as Director of the International Program in Industrial Development Chapel Hill NC as Supervisor of the Environmental Control Laboratory for Mobay Chemical Corporation Charleston SC and as environmental engineer with Research Triangle Institute NC. Dr. Sims currently is involved in teaching research and technology transfer in the area of contaminated soil characterization and remediation. Research Assistant Professor in the Division of Environmental Engineering at Utah State University. She holds degrees in biology (B.S.) environmental chemistry and biology (M.S.) and soil science (M.S.). She has held positions as an Associate in a private consulting firm in Raleigh NC and as Chairperson of the on-site wastewater disposal committee of the State of Utah. Judith Sims is currently involved in teaching research and technology transfer in the area of contaminated soil characterization and remediation.

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Nanomaterials in the treatment and diagnosis of rheumatoid arthritis: Advanced approaches

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SLAS technology 2024年第4期29卷 100146-100146页

作者： Angela, Stefanny Fadhilah, Gianna Hsiao, Wesley Wei-Wen Lin, Hsuan-Yi Ko, Joshua Lu, Steven Che-Wei Lee, Cheng-Chung Chang, Yu-Sheng Lin, Ching-Yu Chang, Huan-Cheng Chiang, Wei-Hung Department of Chemical Engineering National Taiwan University of Science and Technology Taipei Taiwan Department of Power Mechanical Engineering National Tsing Hua University Hsinchu Taiwan Ph.D. Program for Translational Medicine College of Medical Science and Technology Taipei Medical University Taipei Taiwan Division of Allergy Immunology and Rheumatology Department of Internal Medicine Shuang Ho Hospital New Taipei City Taiwan Division of Allergy Immunology and Rheumatology Department of Internal Medicine School of Medicine College of Medicine Taipei Medical University Taipei Taiwan The Ph.D. Program in Medical Biotechnology College of Medical Science and Technology Taipei Medical University Taipei Taiwan School of Medical Laboratory Science and Biotechnology College of Medical Science and Technology Taipei Medical University Taipei Taiwan Department of Chemical Engineering National Taiwan University of Science and Technology Taipei Taiwan Institute of Atomic and Molecular Sciences Academia Sinica Taipei Taiwan Department of Chemistry National Taiwan Normal University Taipei Taiwan Department of Chemical Engineering National Taiwan University of Science and Technology Taipei Taiwan Sustainable Electrochemical Energy Development (SEED) Center National Taiwan University of Science and Technology Taipei Taiwan Advanced Manufacturing Research Center National Taiwan University of Science and Technology Taipei Taiwan. Electronic address: weshsiao@mail.ntust.edu.tw

Rheumatoid arthritis (RA), a chronic inflammatory condition that affects persons between the ages of 20 and 40, causes synovium inflammation, cartilage loss, and joint discomfort as some of its symptoms. diagnostic techniques for RA have traditionally been split into two main categories: imaging and serological tests. However, significant issues are associated with both of these methods. Imaging methods are costly and only helpful in people with obvious symptoms, while serological assays are time-consuming and require specialist knowledge. The drawbacks of these traditional techniques have led to the development of novel diagnostic approaches. The unique properties of nanomaterials make them well-suited as biosensors. Their compact dimensions are frequently cited for their outstanding performance, and their positive impact on the signal-to-noise ratio accounts for their capacity to detect biomarkers at low detection limits, with excellent repeatability and a robust dynamic range. In this review, we discuss the use of nanomaterials in RA theranostics. Scientists have recently synthesized, characterized, and modified nanomaterials and biomarkers commonly used to enhance RA diagnosis and therapy capabilities. We hope to provide scientists with the promising potential that nanomaterials hold for future theranostics and offer suggestions on further improving nanomaterials as biosensors, particularly for detecting autoimmune disorders. Copyright © 2024 The Authors. Published by Elsevier Inc. All rights reserved.

关键词： Biomarker Biosensor diagnosis Nanomaterials Rheumatoid arthritis Therapy

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Improvement of extracellular polysaccharides production from Cordyceps militaris immobilized alginate beads in repeated-batch fermentation

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LWT 2024年 193卷

作者： Hou, Shi-Jing Cheng, Kuan-Chen Lin, Shyh-Hsiang Hsiao, I-Lun Santoso, Shella Permatasari Singajaya, Stephanie Chou, Yu-Chieh Lin, Shin-Ping Master Program in Food Safety Taipei Medical University 250 Wu-Hsing Street Taipei11031 Taiwan Institute of Biotechnology National Taiwan University 1 Roosevelt Rd. Sec. 4 Taipei10617 Taiwan Graduate Institute of Food Science and Technology National Taiwan University 1 Roosevelt Rd. Sec. 4 Taipei10617 Taiwan Department of Medical Research China Medical University Hospital China Medical University 91 Hsueh-Shih Rd. Taichung40402 Taiwan Department of Optometry Asia University 500 Lioufeng Rd. Wufeng Taichung41354 Taiwan School of Nutrition and Health Sciences Taipei Medical University 250 Wu-Hsing Street Taipei11031 Taiwan School of Food Safety Taipei Medical University 250 Wu-Hsing Street Taipei11031 Taiwan Department of Chemical Engineering Widya Mandala Surabaya Catholic University Kalijudan 37 East Java Surabaya60114 Indonesia Collaborative Research Center for Sustainable and Zero Waste Industries Kalijudan 37 East Java Surabaya60114 Indonesia Ph.D. Program in Drug Discovery and Development Industry Taipei Medical University 250 Wu-Hsing Street Taipei11031 Taiwan Research Center of Biomedical Device Taipei Medical University 250 Wu-Hsing Street Taipei11031 Taiwan TMU Research Center for Digestive Medicine Taipei Medical University 250 Wu-Hsing Street Taipei11031 Taiwan

Cordyceps militaris (C. militaris) is a unique medicinal fungus of the genus Cordyceps. It has high economic value due to various biological functions from the extracellular polysaccharides (EPSs) it produces. The aim of this study was to establish a mycelium-immobilization system for EPS production in a bubble column system. First, EPS production was optimized by 90.2% (from 0.72 to 1.37 g/L) using response surface methodology under an alginate-immobilized mycelium system with 6 days of cultivation. The highest EPS production was obtained (5.3 g/L) in a flask system through elongation to 15 days of cultivation. EPS production subsequently further increased to 10.42 g/L utilizing a bubble column reactor. Furthermore, the system can be reused for at least three rounds. In the EPS characteristics analysis, the produced EPSs were mainly composed of glucose and galactose. They presented strong antibacterial activity against Staphylococcus aureus. In terms of antioxidant activity, respective the EPS concentration that caused 50% scavenging of dPph and ABTS free radicals values (IC50) were 4.65 and 7.92 mg/mL. In summary, these findings should be helpful for establishing a suitable industrial fermentation system for C. militaris and can be studied in the food and medical industries in future work. © 2024 The Authors

关键词： Mycelium

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development of anti-aflatoxin B1 nanobodies from a novel mutagenesis-derived synthetic library for traditional Chinese medicine and foods safety testing

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Journal of biological engineering 2023年第1期17卷 30页

作者： Yu-Ching Lee Gar-Hwa Lai Tsai-Yu Lin Tien-Sheng Tseng Tsung-Hsun Tsai Wang-Chuan Chen Cheng-Chung Lee Keng-Chang Tsai TMU Research Center of Cancer Translational Medicine Taipei Medical University Taipei Taiwan. Ph.D. Program for Cancer Molecular Biology and Drug Discovery College of Medical Science and Technology Taipei Medical University Taipei Taiwan. Ph.D. Program in Drug Discovery and Development Industry College of Pharmacy Taipei Medical University Taipei Taiwan. Ph.D. Program in Medical Biotechnology College of Medical Science and Technology Taipei Medical University Taipei Taiwan. Department of Orthopedics Kaohsiung Veterans General Hospital Kaohsiung Taiwan. Institute of Molecular Biology National Chung Hsing University Taichung Taiwan. Department of Psychiatry Kaohsiung Armed Forces General Hospital Kaohsiung Taiwan. The School of Chinese Medicine for Post Baccalaureate I-Shou University Kaohsiung Taiwan. Department of Chinese Medicine E-Da Hospital Kaohsiung Taiwan. The Ph.D. Program for Translational Medicine College of Medical Science and Technology Taipei Medical University Taipei Taiwan. Ph.D. Program in Medical Biotechnology College of Medical Science and Technology Taipei Medical University Taipei Taiwan. tkc@nricm.edu.tw. National Research Institute of Chinese Medicine Ministry of Health and Welfare No. 155-1 Sec. 2 Linong St. Beitou District Taipei 11221 Taiwan. tkc@nricm.edu.tw.

BACKGROUNd:The main commercially available methods for detecting small molecules of mycotoxins in traditional Chinese medicine (TCM) and functional foods are enzyme-linked immunosorbent assay and mass spectrometry. Regarding the development of diagnostic antibody reagents, effective methods for the rapid preparation of specific monoclonal antibodies are inadequate. METHOdS:In this study, a novel synthetic phage-displayed nanobody Golden Glove (SynaGG) library with a glove-like cavity configuration was established using phage display technology in synthetic biology. We applied this unique SynaGG library on the small molecule aflatoxin B1 (AFB1), which has strong hepatotoxicity, to isolate specific nanobodies with high affinity for AFB1. RESULT:These nanobodies exhibit no cross-reactivity with the hapten methotrexate, which is recognized by the original antibody template. By binding to AFB1, two nanobodies can neutralize AFB1-induced hepatocyte growth inhibition. Using molecular docking, we found that the unique non-hypervariable complementarity-determining region 4 (CdR4) loop region of the nanobody was involved in the interaction with AFB1. Specifically, the CdR4's positively charged amino acid arginine directed the binding interaction between the nanobody and AFB1. We then rationally optimized the interaction between AFB1 and the nanobody by mutating serine at position 2 into valine. The binding affinity of the nanobody to AFB1 was effectively improved, and this result supported the use of molecular structure simulation for antibody optimization. CONCLUSION:In summary, this study revealed that the novel SynaGG library, which was constructed through computer-aided design, can be used to isolate nanobodies that specifically bind to small molecules. The results of this study could facilitate the development of nanobody materials to detect small molecules for the rapid screening of TCM materials and foods in the future.

关键词： Aflatoxin B1 Glove-like cavity Nanobody Nonhypervariable complementarity-determining region 4 loop phage display technology

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