Regulation of peroxisome proliferator-activated receptor gamma activity by losartan metabolites

Hypertension. 2006 Mar;47(3):586-9. doi: 10.1161/01.HYP.0000196946.79674.8b. Epub 2005 Dec 19.

Abstract

Two active metabolites of the angiotensin type 1 (AT1) receptor blocker losartan have been described previously, EXP3174 and EXP3179. Whereas EXP3174 is the main antihypertensive AT1 receptor-blocking metabolite, the role of EXP3179 is widely unknown. Recently, a subgroup of AT1 receptor blockers has been identified as ligands for the peroxisome proliferator-activated receptor gamma (PPAR-gamma). Here we characterize the PPAR-gamma-activating properties of the 2 active losartan metabolites. PPAR-gamma activity was measured with a chimeric Gal4-DNA-binding domain-hPPARgamma-ligand-binding domain (LBD) fusion protein on a Gal4-dependent luciferase reporter system. EXP3179 prominently induced the activation of the PPAR-gamma-LBD reaching a maximum at 100 micromol/L with a 7.1+/-1-fold induction (P<0.05 versus vehicle-treated cells). Maximum PPAR-gamma-LBD activation by EXP3179 reached 51% of the maximum response induced by the full PPAR-gamma agonist pioglitazone, identifying EXP3179 as a partial PPAR-gamma agonist. EXP3174 did not induce PPAR-gamma-LBD activation. EC50 values were calculated for PPAR-gamma-LBD activity (pioglitazone EC50: 0.88 micromol/L; EXP3179 EC50: 17.1 micromol/L; losartan EC50: >50 micromol/L). Consistent with the activation of PPAR-gamma, EXP3179 potently induced 3T3-L1 adipocyte differentiation, a typical PPAR-gamma-dependent cell function, and markedly stimulated PPAR-gamma target gene expression. EXP3174 failed to regulate differentiation or PPAR-gamma target gene expression. The present study characterizes the active losartan metabolite EXP3179 as a partial PPAR-gamma agonist. PPAR-gamma activation by EXP3179 may help us to understand the beneficial metabolic effects of losartan observed in clinical trials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • Adipocytes / cytology
  • Angiotensin II Type 1 Receptor Blockers / metabolism*
  • Animals
  • COS Cells
  • Cell Differentiation / drug effects
  • Chlorocebus aethiops
  • Gene Expression / drug effects
  • Imidazoles / metabolism
  • Imidazoles / pharmacology*
  • Ligands
  • Losartan / analogs & derivatives*
  • Losartan / metabolism*
  • Losartan / pharmacology
  • Mice
  • PPAR gamma / agonists
  • PPAR gamma / drug effects*
  • PPAR gamma / genetics
  • PPAR gamma / metabolism*
  • Protein Structure, Tertiary / drug effects
  • RNA, Messenger / metabolism
  • Tetrazoles / metabolism
  • Tetrazoles / pharmacology*

Substances

  • Angiotensin II Type 1 Receptor Blockers
  • Imidazoles
  • Ligands
  • PPAR gamma
  • RNA, Messenger
  • Tetrazoles
  • 2-butyl-4-chloro-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-imidazole-5-carboxaldehyde
  • losartan carboxylic acid
  • Losartan