Synthesis of biotinylated episilvestrol: highly selective targeting of the translation factors eIF4AI/II

Org Lett. 2013 Mar 15;15(6):1406-9. doi: 10.1021/ol400401d. Epub 2013 Mar 5.


Silvestrol (1) and episilvestrol (2) are protein synthesis inhibitors, and the former has shown efficacy in multiple mouse models of cancer; however, the selectivity of these potent cytotoxic natural products has not been described. Herein, it is demonstrated that eukaryotic initiation factors eIF4AI/II were the only proteins detected to bind silvestrol (1) and biotinylated episilvestrol (9) by affinity purification. Our study demonstrates the remarkable selectivity of these promising chemotherapeutics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotinylation
  • Eukaryotic Initiation Factor-4A / antagonists & inhibitors*
  • Humans
  • Mice
  • Protein Synthesis Inhibitors / chemistry
  • Protein Synthesis Inhibitors / pharmacology
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*


  • Protein Synthesis Inhibitors
  • Triterpenes
  • episilvestrol
  • silvestrol
  • Eukaryotic Initiation Factor-4A