13-cis retinoic acid and isomerisation in paediatric oncology--is changing shape the key to success?

Biochem Pharmacol. 2005 May 1;69(9):1299-306. doi: 10.1016/j.bcp.2005.02.003.

Abstract

Retinoic acid isomers have been used with some success as chemotherapeutic agents, most recently with 13-cis retinoic acid showing impressive clinical efficacy in the paediatric malignancy neuroblastoma. The aim of this commentary is to review the evidence that 13-cis retinoic acid is a pro-drug, and consider the implications of retinoid metabolism and isomerisation for the further development of retinoic acid for cancer therapy. The low binding affinity of 13-cis retinoic acid for retinoic acid receptors, low activity in gene expression assays and the accumulation of the all-trans isomer in cells treated with 13-cis retinoic acid, coupled with the more-favourable pharmacokinetic profile of 13-cis retinoic acid compared to other isomers, suggest that intracellular isomerisation to all-trans retinoic acid is the key process underlying the biological activity of 13-cis retinoic acid. Intracellular metabolism of all-trans retinoic acid by a positive auto-regulatory loop may result in clinical resistance to retinoic acid. Agents that block or reduce the metabolism of all-trans retinoic acid are therefore attractive targets for drug development. Devising strategies to deliver 13-cis retinoic acid to tumour cells and facilitate the intracellular isomerisation of 13-cis retinoic acid, while limiting metabolism of all-trans retinoic acid, may have a major impact on the efficacy of 13-cis retinoic acid in paediatric oncology.

Publication types

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

MeSH terms

  • Animals
  • Antineoplastic Agents / metabolism*
  • Antineoplastic Agents / pharmacology
  • Child
  • Humans
  • Isotretinoin / chemistry
  • Isotretinoin / metabolism*
  • Isotretinoin / pharmacology
  • Molecular Structure
  • Neuroblastoma / drug therapy*
  • Neuroblastoma / metabolism*
  • Retinol-Binding Proteins / metabolism
  • Stereoisomerism
  • Tretinoin / chemistry
  • Tretinoin / metabolism*
  • Tretinoin / pharmacology

Substances

  • Antineoplastic Agents
  • Retinol-Binding Proteins
  • Tretinoin
  • Isotretinoin