Reversible carnitine palmitoyltransferase inhibitors with broad chemical diversity as potential antidiabetic agents

J Med Chem. 2001 Jul 19;44(15):2383-6. doi: 10.1021/jm010889+.

Abstract

A series of carnitine related compounds of general formula XCH(2)CHZRCH(2)Y were evaluated as CPT I inhibitors in intact rat liver (L-CPT I) and heart mitochondria (M-CPT I). Derivative 27 (ZR = -HNSO(2)R, R = C(12), X = trimethylammonium, Y = carboxylate, (R) form) showed the highest activity (IC(50) = 0.7 microM) along with a good selectivity (M-CPT I/L-CPTI IC(50) ratio = 4.86). Diabetic db/db mice treated orally with 27 showed a significant reduction of serum glucose levels.

MeSH terms

  • 3-Hydroxybutyric Acid / blood
  • Animals
  • Carnitine / analogs & derivatives*
  • Carnitine / chemical synthesis*
  • Carnitine / chemistry
  • Carnitine / pharmacology
  • Carnitine O-Palmitoyltransferase / antagonists & inhibitors*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Hypoglycemic Agents / chemical synthesis*
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / pharmacology
  • In Vitro Techniques
  • Mitochondria, Heart / drug effects
  • Mitochondria, Heart / metabolism
  • Mitochondria, Liver / drug effects
  • Mitochondria, Liver / metabolism
  • Rats
  • Rats, Sprague-Dawley
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Hypoglycemic Agents
  • Carnitine O-Palmitoyltransferase
  • Carnitine
  • 3-Hydroxybutyric Acid