Potent farnesyltransferase inhibitors with 1,4-diazepane scaffolds as novel destabilizing microtubule agents in hormone-resistant prostate cancer

J Med Chem. 2011 Mar 10;54(5):1178-90. doi: 10.1021/jm101067y. Epub 2011 Feb 7.

Abstract

A new class of potent farnesyltransferase inhibitors based on a 1,4-diazepane scaffold was synthesized with protein farnesyltransferase inhibition potencies in the low nanomolar range. The compounds block the growth on two hormone-resistant tumor prostatic cell lines (DU145 and PC3). The advanced cellular evaluation of the more potent farnesyltransferase inhibitors was explored and revealed a disorganization of tubulin in PC3 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androgen Antagonists / therapeutic use*
  • Azepines / chemical synthesis*
  • Azepines / pharmacokinetics
  • Azepines / pharmacology
  • Cell Line
  • Cell Line, Tumor
  • Drug Resistance, Neoplasm
  • Drug Screening Assays, Antitumor
  • Farnesyltranstransferase / antagonists & inhibitors*
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Male
  • Models, Molecular
  • Prostatic Neoplasms / drug therapy*
  • Structure-Activity Relationship
  • Tubulin / drug effects
  • Tubulin / ultrastructure
  • Tubulin Modulators / chemical synthesis*
  • Tubulin Modulators / pharmacokinetics
  • Tubulin Modulators / pharmacology

Substances

  • 1,4-diazepane
  • Androgen Antagonists
  • Azepines
  • Tubulin
  • Tubulin Modulators
  • Farnesyltranstransferase