Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 316-322Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.29
Keywords
cytotoxicity; diazirines; dolastatin analogs; marine natural products; peptides; total synthesis
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The marine natural product malevamide D from the cyanobacterium Symploca hydnoides was synthesized for the first time. The final peptide coupling linked the dolaisoleuine and dolaproine subunits. The phenyl group of malevamide D was also functionalized with a photoreactive diazirine moiety, which was carried through seven reaction steps. Comprehensive assessment of the cytotoxicity in a panel of 42 human cancer cell lines revealed a geomean IC70 value of 1.5 nM (IC50 0.7 nM) for malevamide D, whereas the photoreactive derivative proved to be less active by a factor of at least 200. COMPARE analysis indicated tubulin interaction as likely mode of action of malevamide D.
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