Crystal Structures of mPGES-1 Inhibitor Complexes Form a Basis for the Rational Design of Potent Analgesic and Anti-Inflammatory Therapeutics

J Med Chem. 2015 Jun 11;58(11):4727-37. doi: 10.1021/acs.jmedchem.5b00330. Epub 2015 May 20.

Abstract

Microsomal prostaglandin E synthase 1 (mPGES-1) is an α-helical homotrimeric integral membrane inducible enzyme that catalyzes the formation of prostaglandin E2 (PGE2) from prostaglandin H2 (PGH2). Inhibition of mPGES-1 has been proposed as a therapeutic strategy for the treatment of pain, inflammation, and some cancers. Interest in mPGES-1 inhibition can, in part, be attributed to the potential circumvention of cardiovascular risks associated with anti-inflammatory cyclooxygenase 2 inhibitors (coxibs) by targeting the prostaglandin pathway downstream of PGH2 synthesis and avoiding suppression of antithrombotic prostacyclin production. We determined the crystal structure of mPGES-1 bound to four potent inhibitors in order to understand their structure-activity relationships and provide a framework for the rational design of improved molecules. In addition, we developed a light-scattering-based thermal stability assay to identify molecules for crystallographic studies.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Analgesics / chemistry*
  • Analgesics / metabolism
  • Analgesics / therapeutic use
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / metabolism
  • Anti-Inflammatory Agents / therapeutic use
  • Crystallography, X-Ray
  • Drug Design*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / metabolism
  • Humans
  • Imidazoles / chemistry*
  • Intramolecular Oxidoreductases / chemistry*
  • Intramolecular Oxidoreductases / metabolism
  • Microsomes / enzymology
  • Models, Molecular
  • Molecular Sequence Data
  • Molecular Structure
  • Prostaglandin-E Synthases
  • Protein Conformation
  • Sequence Homology, Amino Acid

Substances

  • Analgesics
  • Anti-Inflammatory Agents
  • Enzyme Inhibitors
  • Imidazoles
  • Intramolecular Oxidoreductases
  • PTGES protein, human
  • Prostaglandin-E Synthases

Associated data

  • PDB/4YK5
  • PDB/4YL0
  • PDB/4YL1
  • PDB/4YL3