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

by Hirsch, Melissa; Zong, Guanghui; Mondrik, Collin; Hu, Zhijan; Shi, Wei

Ipomoeassin F is a plant-derived macrocyclic glycolipid with single-digit nanomolar IC50 values against cancer cell growth. Previous structure-activity relationship studies have demonstrated that specific modifications around the fucoside ring moiety of Ipomoeassin F do not significantly alter the cytotoxicity of the compd. To further elucidate the effect of this structure on the biol. activity and potentially improve the cost and efficiency of the synthesis route, a fucose-truncated monosaccharide analog was designed and synthesized. Subsequent biol. evaluation against the breast cancer cell lines MDA-MB-231 and MCF7 showed that the six-membered ring of the fucoside moiety is essential to retaining the overall conformation and bioactivity of Ipomoeassin F. [on SciFinder(R)]