Identification of furo[3', 2':3,4]naphtho[1,2-d]imidazole derivatives as orally active and selective inhibitors of microsomal prostaglandin E(2) synthase-1 (mPGES-1)

Mol Divers. 2012 May;16(2):215-29. doi: 10.1007/s11030-011-9347-9. Epub 2011 Dec 9.

Abstract

This study describes the synthesis and anti-inflammatory effects of furo[3', 2':3,4]naphtho[1,2-d] imidazole derivatives. Among these furo[3', 2':3,4]naphtho[1,2-d]imidazole derivatives, 2-(4-methoxyphenyl)furo [3', 2':3,4]naphtho[1,2-d]imidazole (12) exhibited a strong inhibitory activity against LPS-induced PGE(2) production, with an IC(50) value of 47 nM. Compound 12 is then further examined for its inhibitory effects in the protein expression of COX-2 and microsomal prostaglandin E(2) synthase-1 (mPGES-1) in Raw 264.7 cells. Our results indicate that compound 12 was capable against inhibiting LPS-induced mPGES-1 protein expression at a concentration of 1.0 μM and no inhibitory effect in COX-2 expression. The sepsis-induced PGE(2) production in rat serum decreased ~250% by the pretreatment of 12 at 10 mg/kg. These results are especially important since compound 12 exhibited good oral bioavailability (72%) and was not cytotoxic at a concentration of 10.0 μM. Therefore, compound 12 is a highly selective mPGES-1 inhibitor that can serve as a lead for the development of novel oral anti-inflammatory drug candidates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Administration, Oral
  • Animals
  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / pharmacology*
  • Anti-Inflammatory Agents / toxicity
  • Cell Degranulation / drug effects
  • Cell Line
  • Dinoprostone / metabolism
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Enzyme Inhibitors / toxicity
  • Imidazoles / chemical synthesis
  • Imidazoles / pharmacology*
  • Imidazoles / toxicity
  • Intramolecular Oxidoreductases / antagonists & inhibitors*
  • Lipopolysaccharides / pharmacology
  • Lung / drug effects
  • Lung / pathology
  • Mice
  • Mice, Inbred BALB C
  • Neutrophils / drug effects
  • Neutrophils / physiology
  • Nitric Oxide / metabolism
  • Prostaglandin-E Synthases
  • Quantitative Structure-Activity Relationship
  • Rats
  • Rats, Sprague-Dawley
  • Sepsis / metabolism
  • Sepsis / pathology
  • Superoxides / metabolism

Substances

  • Anti-Inflammatory Agents
  • Enzyme Inhibitors
  • Imidazoles
  • Lipopolysaccharides
  • Superoxides
  • Nitric Oxide
  • Intramolecular Oxidoreductases
  • Prostaglandin-E Synthases
  • Ptges protein, mouse
  • Dinoprostone