Identification and characterization of 4-chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide (GSK3787), a selective and irreversible peroxisome proliferator-activated receptor delta (PPARdelta) antagonist

J Med Chem. 2010 Feb 25;53(4):1857-61. doi: 10.1021/jm900464j.

Abstract

4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide 3 (GSK3787) was identified as a potent and selective ligand for PPARdelta with good pharmacokinetic properties. A detailed binding study using mass spectral analysis confirmed covalent binding to Cys249 within the PPARdelta binding pocket. Gene expression studies showed that pyridylsulfone 3 antagonized the transcriptional activity of PPARdelta and inhibited basal CPT1a gene transcription. Compound 3 is a PPARdelta antagonist with utility as a tool to elucidate PPARdelta cell biology and pharmacology.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Benzamides / chemical synthesis*
  • Benzamides / pharmacokinetics
  • Benzamides / pharmacology
  • Binding Sites
  • Carnitine O-Palmitoyltransferase / biosynthesis
  • Carnitine O-Palmitoyltransferase / genetics
  • Cell Line, Tumor
  • Cysteine / metabolism
  • Drug Screening Assays, Antitumor
  • Genes, Reporter
  • Humans
  • Ligands
  • Male
  • Mass Spectrometry
  • Mice
  • Mice, Inbred C57BL
  • Muscle Fibers, Skeletal / drug effects
  • Muscle Fibers, Skeletal / enzymology
  • PPAR delta / agonists
  • PPAR delta / antagonists & inhibitors*
  • PPAR delta / genetics
  • Protein Serine-Threonine Kinases / biosynthesis
  • Protein Serine-Threonine Kinases / genetics
  • Pyruvate Dehydrogenase Acetyl-Transferring Kinase
  • Structure-Activity Relationship
  • Sulfones / chemical synthesis*
  • Sulfones / pharmacokinetics
  • Sulfones / pharmacology
  • Tissue Distribution
  • Transcription, Genetic / drug effects

Substances

  • 4-chloro-N-(2-((5-trifluoromethyl-2-pyridyl)sulfonyl)ethyl)benzamide
  • Antineoplastic Agents
  • Benzamides
  • Ligands
  • PPAR delta
  • Pyruvate Dehydrogenase Acetyl-Transferring Kinase
  • Sulfones
  • Carnitine O-Palmitoyltransferase
  • Protein Serine-Threonine Kinases
  • Cysteine