Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors

J Med Chem. 2012 Sep 27;55(18):8164-77. doi: 10.1021/jm301121j. Epub 2012 Sep 18.

Abstract

Among 18 human chemokine receptors, CCR1, CCR4, CCR5, and CCR8 were activated by metal ion Zn(II) or Cu(II) in complex with 2,2'-bipyridine or 1,10-phenanthroline with similar potencies (EC(50) from 3.9 to 172 μM). Besides being agonists, they acted as selective allosteric enhancers of CCL3. These actions were dependent on a conserved glutamic acid at TM-7 (VII:06/7.39). A screening of 20 chelator analogues in complex with Zn(II) identified compounds with increased potencies, with 7 reaching highest potency at CCR1 (EC(50) of 0.85 μM), 20 at CCR8 (0.39 μM), and 8 at CCR5 (1.0 μM). Altered selectivity for CCR1 and CCR8 over CCR5 (11, 12) and a receptor-dependent separation of allosteric from intrinsic properties were achieved (20). The pocket similarities of CCR1 and CCR8, contrary to CCR5 as proposed by the ligand screen, were elaborated by computational modeling. These studies facilitate exploration of chemokine receptors as possible targets for therapeutic intervention.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allosteric Regulation / drug effects
  • Animals
  • Binding Sites
  • COS Cells
  • Chelating Agents / chemistry
  • Chlorocebus aethiops
  • Copper / chemistry
  • Glutamic Acid
  • Humans
  • Ligands
  • Models, Molecular
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / metabolism
  • Organometallic Compounds / pharmacology*
  • Protein Structure, Tertiary
  • Pyridines / chemistry
  • Receptors, CCR / agonists
  • Receptors, CCR / chemistry
  • Receptors, CCR / metabolism*
  • Substrate Specificity
  • Zinc / chemistry

Substances

  • Chelating Agents
  • Ligands
  • Organometallic Compounds
  • Pyridines
  • Receptors, CCR
  • Glutamic Acid
  • Copper
  • Zinc