A chemical modification of a peroxisome proliferator-activated receptor pan agonist produced a shift to a new dual alpha/gamma partial agonist endowed with mitochondrial pyruvate carrier inhibition and antidiabetic properties

Eur J Med Chem. 2024 Sep 5:275:116567. doi: 10.1016/j.ejmech.2024.116567. Epub 2024 Jun 9.

Abstract

New analogs of the PPAR pan agonist AL29-26 encompassed ligand (S)-7 showing potent activation of PPARα and -γ subtypes as a partial agonist. In vitro experiments and docking studies in the presence of PPAR antagonists were performed to help interpretation of biological data and investigate the main interactions at the binding sites. Further in vitro experiments showed that (S)-7 induced anti-steatotic effects and enhancement of the glucose uptake. This latter effect could be partially ascribed to a significant inhibition of the mitochondrial pyruvate carrier demonstrating that (S)-7 also acted through insulin-independent mechanisms. In vivo experiments showed that this compound reduced blood glucose and lipid levels in a diabetic mice model displaying no toxicity on bone, kidney, and liver. To our knowledge, this is the first example of dual PPARα/γ partial agonist showing these combined effects representing, therefore, the potential lead of new drugs for treatment of dyslipidemic type 2 diabetes.

Keywords: Anti-steatotic effects; Crystallographic studies; Docking experiments; Glucose uptake; MPC inhibition; PPAR dual-agonist.

MeSH terms

  • Animals
  • Diabetes Mellitus, Experimental / drug therapy
  • Diabetes Mellitus, Experimental / metabolism
  • Diabetes Mellitus, Type 2 / drug therapy
  • Diabetes Mellitus, Type 2 / metabolism
  • Dose-Response Relationship, Drug
  • Humans
  • Hypoglycemic Agents* / chemical synthesis
  • Hypoglycemic Agents* / chemistry
  • Hypoglycemic Agents* / pharmacology
  • Male
  • Mice
  • Mitochondria / drug effects
  • Mitochondria / metabolism
  • Molecular Docking Simulation
  • Molecular Structure
  • Monocarboxylic Acid Transporters / antagonists & inhibitors
  • Monocarboxylic Acid Transporters / metabolism
  • PPAR alpha* / agonists
  • PPAR alpha* / metabolism
  • PPAR gamma* / agonists
  • PPAR gamma* / metabolism
  • Structure-Activity Relationship

Substances

  • PPAR alpha
  • PPAR gamma
  • Hypoglycemic Agents
  • Monocarboxylic Acid Transporters