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Title: Cytotoxic metabolites from the endophytic fungus Penicillium chermesinum: Discovery of a cysteine-targeted Michael acceptor as a pharmacophore for fragment-based drug discovery, bioconjugation and click reactions
Authors: Cici Darsih
Vilailak Prachyawarakorn
Suthep Wiyakrutta
Chulabhorn Mahidol
Somsak Ruchirawat
Prasat Kittakoop
Chemical Biology Program
Chulabhorn Research Institute
Mahidol University
South Carolina Commission on Higher Education
Keywords: Chemical Engineering;Chemistry
Issue Date: 11-Aug-2015
Citation: RSC Advances. Vol.5, No.86 (2015), 70595-70603
Abstract: © The Royal Society of Chemistry 2015. Fungal metabolites (1-8) including known compounds, TMC-264 (1), PR-toxin (6) and a sesquiterpene (7), and new natural products 2-5 and 8, were isolated from the mangrove endophytic fungus Penicillium chermesinum. Compound 2 was a novel tetracyclic polyketide uniquely spiro-attached with a γ-lactone ring. Compounds 1 and 6 exhibited comparable cytotoxic activity to that of doxorubicin, and they selectively exhibited activity toward certain cancer cell lines. The cytotoxicity of 1 might be due to the β-chloro substituted α,β-unsaturated ketone functionality, which was reactive toward glutathione and peptides containing a thiol group. The polyketide 1 reacted with glutathione and peptides under physiological conditions, and its thiol-reactive pharmacophore is possibly applicable to the design of glutathione modulation agents, fragment-based drug discovery (for irreversible enzyme inhibitors), bioconjugation, and click reactions. Facile C-S bond formation in water (catalyst-free conditions) inspired by 1 could also be useful for green chemistry.
ISSN: 20462069
Appears in Collections:Scopus 2011-2015

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