Synthesis and cytotoxicity of 2,3-enopyranosyl C-linked conjugates of genistein

Molecules. 2014 May 30;19(6):7072-93. doi: 10.3390/molecules19067072.

Abstract

A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15-17 were synthesized by treating ω-bromoalkyl C-glycosides derived from L-rhamnal (1) with a tetrabutylammonium salt of genistein. The new, metabolically stable analogs of previously studied O-glycosidic genistein derivatives inhibited proliferation of cancer cell lines through inhibition of the cell cycle.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Cell Cycle / drug effects
  • Cell Line
  • Cell Proliferation / drug effects
  • Genistein / chemistry*
  • Genistein / pharmacology*
  • Glycosylation
  • HCT116 Cells
  • Humans
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry

Substances

  • Antineoplastic Agents
  • Quaternary Ammonium Compounds
  • tetrabutylammonium
  • Genistein