Discovery of novel PPAR ligands by a virtual screening approach based on pharmacophore modeling, 3D shape, and electrostatic similarity screening

J Med Chem. 2008 Oct 23;51(20):6303-17. doi: 10.1021/jm800128k. Epub 2008 Sep 27.

Abstract

Peroxisome proliferator-activated receptors (PPARs) are important targets for drugs used in the treatment of atherosclerosis, dyslipidaemia, obesity, type 2 diabetes, and other diseases caused by abnormal regulation of the glucose and lipid metabolism. We applied a virtual screening workflow based on a combination of pharmacophore modeling with 3D shape and electrostatic similarity screening techniques to discover novel scaffolds for PPAR ligands. From the resulting 10 virtual screening hits, five tested positive in human PPAR ligand-binding domain (hPPAR-LBD) transactivation assays and showed affinities for PPAR in a competitive binding assay. Compounds 5, 7, and 8 were identified as PPAR-alpha agonists, whereas compounds 2 and 9 showed agonistic activity for hPPAR-gamma. Moreover, compound 9 was identified as a PPAR-delta antagonist. These results demonstrate that our virtual screening protocol is able to enrich novel scaffolds for PPAR ligands that could be useful for drug development in the area of atherosclerosis, dyslipidaemia, and type 2 diabetes.

MeSH terms

  • Cell Line, Tumor
  • Chemical Phenomena
  • Chemistry, Physical
  • Combinatorial Chemistry Techniques
  • Drug Evaluation, Preclinical*
  • Humans
  • Imaging, Three-Dimensional*
  • Ligands
  • Models, Molecular*
  • Peroxisome Proliferator-Activated Receptors / agonists
  • Peroxisome Proliferator-Activated Receptors / chemistry*
  • Peroxisome Proliferator-Activated Receptors / genetics
  • Peroxisome Proliferator-Activated Receptors / metabolism*
  • Protein Structure, Tertiary
  • Static Electricity
  • Structure-Activity Relationship
  • Transcriptional Activation / genetics

Substances

  • Ligands
  • Peroxisome Proliferator-Activated Receptors