Publication: Design, Synthesis and Evaluations of New 10-Triazolyl-1-methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells
Issued Date
2020-08-14
Resource Type
ISSN
23656549
Other identifier(s)
2-s2.0-85089589454
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
ChemistrySelect. Vol.5, No.30 (2020), 9540-9546
Suggested Citation
Patamawadee Silalai, Uthaiwan Sirion, Pawinee Piyachaturawat, Arthit Chairoungdua, Kanoknetr Suksen, Rungnapha Saeeng Design, Synthesis and Evaluations of New 10-Triazolyl-1-methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells. ChemistrySelect. Vol.5, No.30 (2020), 9540-9546. doi:10.1002/slct.202001908 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/59037
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Design, Synthesis and Evaluations of New 10-Triazolyl-1-methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells
Other Contributor(s)
Abstract
© 2020 Wiley-VCH GmbH Genipin 1, derived from geniposide present in the fruit of Gardenia jasminoides Ellis has been reported to show diverse pharmacological activity. In this work, a new series of genipin-triazole analogues was designed and synthesized yielding high yields from naturally genipin and their cytotoxicity evaluated against six cancer cell lines. Twenty-seven analogues were obtained using a convenient four-step reaction methods. Six analogues showed higher cytotoxic activity than the original genipin and benzylether-triazolegenipin 5 j exhibited the strongest activity against P-388 and A-549 cancer cell lines with IC50 values of 2.54 and 4.53 μM. The structure-activity relationships (SARs) study indicated that the introduction of dibenzyl ether, substituted silyl and long chain aliphatic-triazoles at C-10 position of genipin were most effective in improving cytotoxicity. Molecular docking results provided the information for further modification of genipin scaffold for development as cytotoxic agent.