Identification of potent, selective non-peptide CC chemokine receptor-3 antagonist that inhibits eotaxin-, eotaxin-2-, and monocyte chemotactic protein-4-induced eosinophil migration

J Biol Chem. 2000 Nov 24;275(47):36626-31. doi: 10.1074/jbc.M006613200.

Abstract

Eosinophils have been implicated in the pathogenesis of asthma and other allergic diseases. Several CC chemokines including eotaxin (CCL-11), eotaxin-2 (CCL-24), RANTES (CCL-5), and monocyte chemotactic protein-3 (MCP-3, CCL-7) and 4 (MCP-4, CCL-13) are potent eosinophil chemotactic and activating peptides acting through CC chemokine receptor-3 (CCR3). Thus, antagonism of CCR3 could have a therapeutic role in asthma and other eosinophil-mediated diseases. A high throughput, cellular functional screen was configured using RBL-2H3 cells stably expressing CCR3 (RBL-2H3-CCR3) to identify non-peptide receptor antagonists. A small molecule CCR3 antagonist was identified, SK&F 45523, and chemical optimization led to the generation of a number of highly potent, selective CCR3 antagonists including SB-297006 and SB-328437. These compounds were further characterized in vitro and demonstrated high affinity, competitive inhibition of (125)I-eotaxin and (125)I-MCP-4 binding to human eosinophils. The compounds were potent inhibitors of eotaxin- and MCP-4-induced Ca(2+) mobilization in RBL-2H3-CCR3 cells and eosinophils. Additionally, SB-328437 inhibited eosinophil chemotaxis induced by three ligands that activate CCR3 with similar potencies. Selectivity was affirmed using a panel of 10 seven-transmembrane receptors. This is the first description of a non-peptide CCR3 antagonist, which should be useful in further elucidating the pathophysiological role of CCR3 in allergic inflammatory diseases.

MeSH terms

  • Asthma / physiopathology
  • Benzamides / pharmacology*
  • Binding, Competitive
  • Calcium / metabolism
  • Cell Line
  • Cell Movement / drug effects*
  • Chemokine CCL11
  • Chemokine CCL24
  • Chemokines, CC / antagonists & inhibitors*
  • Cytokines / antagonists & inhibitors*
  • Eosinophils / drug effects*
  • Humans
  • Monocyte Chemoattractant Proteins / antagonists & inhibitors*
  • Naphthalenes / pharmacology*
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / pharmacology
  • Receptors, CCR3
  • Receptors, Chemokine / antagonists & inhibitors*
  • Receptors, Chemokine / physiology
  • Receptors, HIV / antagonists & inhibitors*

Substances

  • Benzamides
  • CCL11 protein, human
  • CCL13 protein, human
  • CCL24 protein, human
  • CCR3 protein, human
  • Chemokine CCL11
  • Chemokine CCL24
  • Chemokines, CC
  • Cytokines
  • Monocyte Chemoattractant Proteins
  • Naphthalenes
  • Receptors, CCR3
  • Receptors, Chemokine
  • Receptors, HIV
  • SB 297006
  • SB 328437
  • SK&F 45523
  • Phenylalanine
  • Calcium