Modified acidic nonsteroidal anti-inflammatory drugs as dual inhibitors of mPGES-1 and 5-LOX

J Med Chem. 2012 Oct 25;55(20):8958-62. doi: 10.1021/jm3010543. Epub 2012 Oct 9.

Abstract

mPGES-1 is a promising target for development of new anti-inflammatory drugs. We aimed to create mPGES-1 inhibitors by modifying the structure of NSAIDs by replacing the carboxylic acid functionality by sulfonamide moieties. Compounds were also tested for 5-LOX inhibition. The most potent mPGES-1 inhibitor was lonazolac derivative 22 (IC₅₀ = 0.16 μM), while the best 5-LOX inhibition was attained by indomethacin derivative 17 (IC₅₀ = 0.9 μM). Inhibition of COX-1 activity was completely removed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Arachidonate 5-Lipoxygenase / metabolism*
  • Cell Line
  • Humans
  • Indomethacin / analogs & derivatives
  • Indomethacin / chemical synthesis
  • Indomethacin / chemistry
  • Indomethacin / pharmacology
  • Intramolecular Oxidoreductases / antagonists & inhibitors*
  • Lipoxygenase Inhibitors / chemical synthesis*
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / pharmacology
  • Microsomes / drug effects
  • Microsomes / metabolism
  • Prostaglandin-E Synthases
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Lipoxygenase Inhibitors
  • Pyrazoles
  • Sulfonamides
  • lonazolac
  • Arachidonate 5-Lipoxygenase
  • Intramolecular Oxidoreductases
  • PTGES protein, human
  • Prostaglandin-E Synthases
  • Indomethacin