Chiral inversion of 2-arylpropionyl-CoA esters by human α-methylacyl-CoA racemase 1A (P504S)--a potential mechanism for the anti-cancer effects of ibuprofen

Chem Commun (Camb). 2011 Jul 14;47(26):7332-4. doi: 10.1039/c1cc10763a. Epub 2011 May 26.

Abstract

Metabolic chiral inversion of 2-arylpropanoic acids (2-APAs;'profens'), such as ibuprofen, is important for pharmacological activity. Several 2-APA-CoA esters were good racemisation substrates for human AMACR 1A, suggesting a common chiral inversion pathway for all 2-APAs and an additional mechanism for their anti-cancer properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / metabolism*
  • Antineoplastic Agents / pharmacology
  • Catalytic Domain
  • Esters
  • Humans
  • Ibuprofen / chemistry*
  • Ibuprofen / metabolism*
  • Ibuprofen / pharmacology
  • Models, Molecular
  • Mycobacterium tuberculosis / enzymology
  • Protein Binding
  • Racemases and Epimerases / chemistry
  • Racemases and Epimerases / metabolism*
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Esters
  • Racemases and Epimerases
  • alpha-methylacyl-CoA racemase
  • Ibuprofen