Synthesis and biological evaluation of colchicine B-ring analogues tethered with halogenated benzyl moieties

J Med Chem. 2012 Dec 27;55(24):11062-6. doi: 10.1021/jm301151t. Epub 2012 Dec 7.

Abstract

Deacetylcolchicine was reacted with substituted benzyl halides to provide a library of compounds for biological analysis. Compound 7 (3,4-difluorobenzyl-N-aminocolchicine) was shown to possess cytotoxicity in cancer cell lines in the low nanomolar range. Significantly, it showed no loss of activity in the resistant A2780AD ovarian carcinoma cell line known to overexpress the ABCB1 drug transporter and was also unaffected by overexpression of class III β-tubulin in HeLa transfected cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP-Binding Cassette Transporters / biosynthesis
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Binding Sites
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Colchicine / analogs & derivatives*
  • Colchicine / chemical synthesis*
  • Colchicine / chemistry
  • Colchicine / pharmacology
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Drug Screening Assays, Antitumor
  • Humans
  • Microtubules / drug effects
  • Microtubules / ultrastructure
  • Models, Molecular
  • Structure-Activity Relationship
  • Transfection
  • Tubulin / chemistry
  • Tubulin / genetics
  • Tubulin / metabolism
  • Tubulin Modulators / chemical synthesis*
  • Tubulin Modulators / pharmacology

Substances

  • (3,4-difluorobenzyl-N-aminocolchicine)
  • ATP-Binding Cassette Transporters
  • Antineoplastic Agents
  • Tubulin
  • Tubulin Modulators
  • Colchicine