Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha

Bioorg Med Chem Lett. 2002 Feb 11;12(3):333-5. doi: 10.1016/s0960-894x(01)00732-6.

Abstract

Optically active phenylpropanoic acid derivatives [(S)-5, and (R)-5] were prepared, and their affinities for peroxisome proliferator-activated receptor (PPAR)alpha and PPAR gamma were evaluated. Binding assay and cell-based reporter assay indicated that the activity of these compounds is enantio-dependent, and resides exclusively on the (S)-isomer.

MeSH terms

  • Crystallography, X-Ray
  • Humans
  • Molecular Conformation
  • Phenylpropionates / chemical synthesis*
  • Phenylpropionates / pharmacology*
  • Protein Binding
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Transcription Factors / agonists*
  • Transcriptional Activation

Substances

  • Phenylpropionates
  • Receptors, Cytoplasmic and Nuclear
  • Transcription Factors