Thiocolchicine-podophyllotoxin conjugates: dynamic libraries based on disulfide exchange reaction

J Org Chem. 2006 Mar 31;71(7):2848-53. doi: 10.1021/jo052677g.

Abstract

A dynamic combinatorial library of thiocolchicine-podophyllotoxin derivatives based on the disulfide bond exchange reaction is described. The influence of a biological target on the composition of the reaction mixture has been demonstrated. Use of high-resolution ESI mass spectrometry to evaluate the composition of the mixture shows promise for the design of new large libraries. The biological evaluation demonstrates that formation of a divalent compound affords a new chemical entity whose biological activity is not merely the sum of the single ligands activities, thus reflecting a different interaction with the biological target.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chromatography, High Pressure Liquid / methods
  • Colchicine / analogs & derivatives*
  • Colchicine / chemistry
  • Colchicine / pharmacology
  • Combinatorial Chemistry Techniques / methods*
  • Disulfides / chemistry*
  • Disulfides / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • In Vitro Techniques
  • Molecular Conformation
  • Podophyllotoxin / chemistry*
  • Podophyllotoxin / pharmacology
  • Sensitivity and Specificity
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Stereoisomerism

Substances

  • Disulfides
  • thiocholchicine
  • Podophyllotoxin
  • Colchicine