Synthesis and cytotoxicity evaluation of 22,23-oxygenated stigmastane derivatives

Bioorg Med Chem. 2008 Feb 1;16(3):1460-73. doi: 10.1016/j.bmc.2007.10.056. Epub 2007 Oct 22.

Abstract

Starting from (22E)-3alpha,5alpha-cyclo-6beta-methoxystigmast-22-ene eighteen derivatives of (22S,23S)-22,23-oxidostigmastane, (22R,23R)-22,23-oxidostigmastane, and (22R,23R)-22,23-dihydroxystigmastane were synthesized and screened for cytotoxicity in human hepatoma Hep G2 cells and human breast carcinoma MCF-7 cells using MTT assay. Four compounds of this series exhibited high cytotoxicity in both cells; three compounds were selectively toxic in MCF-7 cells, one compound was toxic in Hep G2 cells, rather than in MCF-7 cells; four compounds at low concentrations increased MTT test values over the control.

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cholestenones / chemical synthesis*
  • Cholestenones / chemistry
  • Cholestenones / toxicity*
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Oxygen / chemistry*
  • Protons
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Cholestenones
  • Protons
  • Oxygen