A novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: design and synthesis of isotaxel

J Med Chem. 2003 Aug 28;46(18):3782-4. doi: 10.1021/jm034112n.

Abstract

A novel water-soluble paclitaxel prodrug, isotaxel 2, that realizes a higher water-solubility and the formation of paclitaxel through a simple pH-dependent chemical mechanism via the O-N acyl migration was synthesized and showed promising results in water-solubility and kinetics. This prodrug, a 2'-O-benzoyl isoform of paclitaxel, has no additional functional auxiliaries released during conversion to paclitaxel, which would be a great advantage in toxicology and medical economics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Hydrogen-Ion Concentration
  • Kinetics
  • Paclitaxel / administration & dosage*
  • Paclitaxel / analogs & derivatives
  • Paclitaxel / chemical synthesis*
  • Paclitaxel / chemistry
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Solubility
  • Water

Substances

  • Antineoplastic Agents
  • Prodrugs
  • isotaxel
  • Water
  • Paclitaxel