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Design, synthesis and biological evaluation of fucose-truncated monosaccharide analogues of ipomoeassin F.

ABSTRACT: Ipomoeassin F is a plant-derived macrocyclic glycolipid with single-digit nanomolar IC₅₀ values against cancer cell growth. In previous structure-activity relationship studies, we have demonstrated that certain modifications around the fucoside moiety did not cause significant cytotoxicity loss. To further elucidate the effect of the fucoside moiety on the biological activity, we describe here the design and synthesis of several fucose-truncated monosaccharide analogues of ipomoeassin F. Subsequent biological evaluation strongly suggests that the 6-membered ring of the fucoside moiety is essential to the overall conformation of the molecule, thereby influencing bioactivity.

SUBMITTER: Zong G

PROVIDER: S-EPMC5502735 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Design, synthesis and biological evaluation of fucose-truncated monosaccharide analogues of ipomoeassin F.

Zong Guanghui G Hirsch Melissa M Mondrik Collin C Hu Zhijian Z Shi Wei Q WQ

Bioorganic & medicinal chemistry letters 20170421 12

Ipomoeassin F is a plant-derived macrocyclic glycolipid with single-digit nanomolar IC<sub>50</sub> values against cancer cell growth. In previous structure-activity relationship studies, we have demonstrated that certain modifications around the fucoside moiety did not cause significant cytotoxicity loss. To further elucidate the effect of the fucoside moiety on the biological activity, we describe here the design and synthesis of several fucose-truncated monosaccharide analogues of ipomoeassin ...[more]

PMID: 28465102

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