Benzylamide antagonists of protease activated receptor 2 with anti-inflammatory activity

Bioorg Med Chem Lett. 2016 Feb 1;26(3):986-991. doi: 10.1016/j.bmcl.2015.12.048. Epub 2015 Dec 17.

Abstract

Activation of protease activated receptor 2 (PAR2) has been implicated in inflammatory and metabolic disorders and its inhibition may yield novel therapeutics. Here, we report a series of PAR2 antagonists based on C-terminal capping of 5-isoxazolyl-L-cyclohexylalanine-L-isoleucine, with benzylamine analogues being effective new PAR2 antagonists. 5-Isoxazolyl-L-cyclohexylalanine-L-isoleucine-2-methoxybenzylamine (10) inhibited PAR2-, but not PAR1-, induced release of Ca(2+) (IC50 0.5 μM) in human colon cells, IL-6 and TNFα secretion (IC50 1-5 μM) from human kidney cells, and was anti-inflammatory in acute rat paw inflammation (ED50 5 mg/kg sc). These findings show that new benzylamide antagonists of PAR2 have anti-inflammatory activity.

Keywords: Agonist; Antagonist; Benzylamine; Inflammation; Protease activated receptor 2 (PAR2).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Anti-Inflammatory Agents / therapeutic use
  • Calcium / metabolism
  • Cell Line
  • Edema / chemically induced
  • Edema / drug therapy
  • Edema / pathology
  • HT29 Cells
  • Humans
  • Interleukin-6 / metabolism
  • Isoleucine / chemistry
  • Kidney Tubules / cytology
  • Kidney Tubules / drug effects
  • Kidney Tubules / metabolism
  • Phenylalanine / analogs & derivatives
  • Phenylalanine / chemistry
  • Rats
  • Receptor, PAR-2 / agonists
  • Receptor, PAR-2 / antagonists & inhibitors*
  • Receptor, PAR-2 / metabolism
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Anti-Inflammatory Agents
  • Interleukin-6
  • Receptor, PAR-2
  • Tumor Necrosis Factor-alpha
  • Isoleucine
  • cyclohexylalanine
  • Phenylalanine
  • Calcium