A common pharmacophore for cytotoxic natural products that stabilize microtubules

Proc Natl Acad Sci U S A. 1999 Apr 13;96(8):4256-61. doi: 10.1073/pnas.96.8.4256.

Abstract

Taxol (paclitaxel), a complex diterpene obtained from the Pacific yew, Taxus brevifolia, is arguably the most important new drug in cancer chemotherapy. The mechanism of cytotoxic action for paclitaxel-i.e., the stabilization of microtubules leading to mitotic arrest-is now shared by four recently identified natural products, eleutherobin, epothilones A and B, and discodermolide. Their ability to competitively inhibit [3H]paclitaxel binding to microtubules strongly suggests the existence of a common binding site. Recently, we have developed nonaromatic analogues of paclitaxel that maintain high cytotoxicity and tubulin binding (e.g., nonataxel). We now propose a common pharmacophore that unites paclitaxel, nonataxel, the epothilones, eleutherobin, and discodermolide, and rationalizes the extensive structure-activity relationship data pertinent to these compounds. Insights from the common pharmacophore have enabled the development of a hybrid construct with demonstrated cytotoxic and tubulin-binding activity.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / toxicity
  • Alkanes*
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / toxicity
  • Carbamates*
  • Computer Graphics
  • Diterpenes*
  • Epothilones*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / toxicity
  • Lactones / chemistry
  • Lactones / toxicity
  • Magnetic Resonance Spectroscopy / methods
  • Microtubules / drug effects*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Paclitaxel / analogs & derivatives*
  • Paclitaxel / chemistry*
  • Paclitaxel / toxicity
  • Pyrones
  • Thiazoles / chemistry
  • Thiazoles / toxicity

Substances

  • Alkaloids
  • Alkanes
  • Antineoplastic Agents, Phytogenic
  • Carbamates
  • Diterpenes
  • Epothilones
  • Epoxy Compounds
  • Lactones
  • Pyrones
  • Thiazoles
  • eleutherobin
  • discodermolide
  • Paclitaxel
  • epothilone B