Conversion of human-selective PPARalpha agonists to human/mouse dual agonists: a molecular modeling analysis

Bioorg Med Chem Lett. 2004 Dec 20;14(24):6113-6. doi: 10.1016/j.bmcl.2004.09.031.

Abstract

To understand the species selectivity in a series of alpha-methyl-alpha-phenoxy carboxylic acid PPARalpha/gamma dual agonists (1-11), structure-based molecular modeling was carried out in the ligand binding pockets of both human and mouse PPARalpha. This study suggested that interaction of both 4-phenoxy and phenyloxazole substituents of these ligands with F272 and M279 in mouse PPARalpha leads to the species-specific divergence in ligand binding. Insights obtained in the molecular modeling studies of these key interactions resulted in the ability to convert a human-selective PPARalpha agonist to a human and mouse dual agonist within the same platform.

MeSH terms

  • Animals
  • Cinnamates / chemical synthesis*
  • Cinnamates / chemistry
  • Cinnamates / pharmacology
  • Drug Design
  • Humans
  • Ligands
  • Mice
  • Models, Molecular*
  • Molecular Structure
  • PPAR alpha / agonists*
  • Species Specificity
  • Structure-Activity Relationship

Substances

  • Cinnamates
  • Ligands
  • PPAR alpha