Synthetic conjugates of genistein affecting proliferation and mitosis of cancer cells

Bioorg Med Chem. 2011 Jan 1;19(1):295-305. doi: 10.1016/j.bmc.2010.11.024. Epub 2010 Nov 11.


This paper describes the synthesis and antiproliferative activity of conjugates of genistein (1) and unsaturated pyranosides. Constructs linking genistein with a sugar moiety through an alkyl chain were obtained in a two-step synthesis: in a first step genistein was converted into an intermediate bearing an ω-hydroxyalkyl substituent, containing two, three or five carbon atoms, at position 7, while the second step involved Ferrier glycosylation reaction, employing glycals. Antiproliferative activity of several genistein derivatives was tested in cancer cell lines in vitro. The most potent derivative, Ram-3 inhibited the cell cycle, interacted with mitotic spindles and caused apoptotic cell death. Neither genistein nor the sugar alone were able to influence the mitotic spindle organization. Our results indicate, that conjugation of genistein with certain sugars may render the interaction of derivatives with new molecular targets.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Electrophoresis, Agar Gel
  • Genistein / chemical synthesis
  • Genistein / pharmacology*
  • Humans
  • In Situ Nick-End Labeling
  • Magnetic Resonance Spectroscopy
  • Mitosis / drug effects*
  • Spectrometry, Mass, Electrospray Ionization


  • Genistein