A unified and quantitative receptor model for the microtubule binding of paclitaxel and epothilone

Org Lett. 1999 Jul 15;1(1):43-6. doi: 10.1021/ol990521v.

Abstract

[formula: see text] Paclitaxel and epothilone represent the two major classes of antimicrotubule agents that promote tubulin polymerization and, presumably, mitotic arrest during cell division. A common minireceptor binding site model at beta-tubulin has been constructed for these structurally divergent compounds. Utilizing 20 amino acids identified in photoaffinity labeling experiments, the 3-D model correlates measured and predicted Ki's with r = 0.99 and rms(delta Gcalc-delta Gexp) = 0.2 kcal/mol. In addition, the model predicts the affinity of compounds not used in the training set and explains much of the SAR for the paclitaxel and epothilone families.

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism*
  • Epothilones*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / metabolism*
  • Magnetic Resonance Spectroscopy
  • Microtubules / chemistry
  • Microtubules / metabolism*
  • Models, Molecular
  • Monte Carlo Method
  • Paclitaxel / chemistry
  • Paclitaxel / metabolism*
  • Protein Binding
  • Receptors, Drug / chemistry
  • Receptors, Drug / metabolism*
  • Structure-Activity Relationship
  • Thiazoles / chemistry
  • Thiazoles / metabolism*
  • Tubulin / chemistry
  • Tubulin / metabolism

Substances

  • Antineoplastic Agents
  • Epothilones
  • Epoxy Compounds
  • Receptors, Drug
  • Thiazoles
  • Tubulin
  • Paclitaxel
  • epothilone B