BRP-187: A potent inhibitor of leukotriene biosynthesis that acts through impeding the dynamic 5-lipoxygenase/5-lipoxygenase-activating protein (FLAP) complex assembly

Biochem Pharmacol. 2016 Nov 1:119:17-26. doi: 10.1016/j.bcp.2016.08.023. Epub 2016 Aug 31.

Abstract

The pro-inflammatory leukotrienes (LTs) are formed from arachidonic acid (AA) in activated leukocytes, where 5-lipoxygenase (5-LO) translocates to the nuclear envelope to assemble a functional complex with the integral nuclear membrane protein 5-LO-activating protein (FLAP). FLAP, a MAPEG family member, facilitates AA transfer to 5-LO for efficient conversion, and LT biosynthesis critically depends on FLAP. Here we show that the novel LT biosynthesis inhibitor BRP-187 prevents the 5-LO/FLAP interaction at the nuclear envelope of human leukocytes without blocking 5-LO nuclear redistribution. BRP-187 inhibited 5-LO product formation in human monocytes and polymorphonuclear leukocytes stimulated by lipopolysaccharide plus N-formyl-methionyl-leucyl-phenylalanine (IC50=7-10nM), and upon activation by ionophore A23187 (IC50=10-60nM). Excess of exogenous AA markedly impaired the potency of BRP-187. Direct 5-LO inhibition in cell-free assays was evident only at >35-fold higher concentrations, which was reversible and not improved under reducing conditions. BRP-187 prevented A23187-induced 5-LO/FLAP complex assembly in leukocytes but failed to block 5-LO nuclear translocation, features that were shared with the FLAP inhibitor MK886. Whereas AA release, cyclooxygenases and related LOs were unaffected, BRP-187 also potently inhibited microsomal prostaglandin E2 synthase-1 (IC50=0.2μM), another MAPEG member. In vivo, BRP-187 (10mg/kg) exhibited significant effectiveness in zymosan-induced murine peritonitis, suppressing LT levels in peritoneal exudates as well as vascular permeability and neutrophil infiltration. Together, BRP-187 potently inhibits LT biosynthesis in vitro and in vivo, which seemingly is caused by preventing the 5-LO/FLAP complex assembly and warrants further preclinical evaluation.

Keywords: 5-Lipoxygenase; 5-Lipoxygenase-activating protein; Arachidonic acid; Inflammation; Leukotriene.

MeSH terms

  • 5-Lipoxygenase-Activating Proteins / genetics
  • 5-Lipoxygenase-Activating Proteins / metabolism*
  • Animals
  • Arachidonate 5-Lipoxygenase / genetics
  • Arachidonate 5-Lipoxygenase / metabolism*
  • Cell-Free System
  • Gene Expression Regulation, Enzymologic / drug effects
  • HEK293 Cells
  • Humans
  • Hydroxyurea / analogs & derivatives
  • Hydroxyurea / pharmacology
  • Indoles / pharmacology
  • Isoxazoles / chemistry
  • Isoxazoles / metabolism
  • Isoxazoles / pharmacology*
  • Leukotriene Antagonists / chemistry
  • Leukotriene Antagonists / metabolism
  • Leukotriene Antagonists / pharmacology*
  • Leukotrienes / biosynthesis*
  • Male
  • Mice
  • Molecular Structure
  • Peritonitis / chemically induced
  • Peritonitis / drug therapy
  • Quinolines / chemistry
  • Quinolines / metabolism
  • Quinolines / pharmacology*
  • Zymosan / toxicity

Substances

  • 5-Lipoxygenase-Activating Proteins
  • BRP-187
  • Indoles
  • Isoxazoles
  • Leukotriene Antagonists
  • Leukotrienes
  • Quinolines
  • MK-886
  • Zymosan
  • Arachidonate 5-Lipoxygenase
  • zileuton
  • Hydroxyurea