Identification and characterization of small molecule modulators of the Epstein-Barr virus-induced gene 2 (EBI2) receptor

J Med Chem. 2014 Apr 24;57(8):3358-68. doi: 10.1021/jm4019355. Epub 2014 Apr 15.

Abstract

Oxysterols have recently been identified as natural ligands for a G protein-coupled receptor called EBI2 (aka GPR183) ( Nature 2011 , 475 , 524 ; 519 ). EBI2 is highly expressed in immune cells ( J. Biol. Chem. 2006 , 281 , 13199 ), and its activation has been shown to be critical for the adaptive immune response and has been genetically linked to autoimmune diseases such as type I diabetes ( Nature 2010 , 467 , 460 ). Here we describe the isolation of a potent small molecule antagonist for the EBI2 receptor. First, we identified a small molecule agonist NIBR51 (1), which enabled identification of inhibitors of receptor activation. One antagonist called NIBR127 (2) was used as a starting point for a medicinal chemistry campaign, which yielded NIBR189 (4m). This compound was extensively characterized in binding and various functional signaling assays. Furthermore, we have used 4m to block migration of a monocyte cell line called U937, suggesting a functional role of the oxysterol/EBI2 pathway in these immune cells.

MeSH terms

  • Animals
  • CHO Cells
  • Calcium / metabolism
  • Cricetulus
  • Herpesvirus 4, Human*
  • Humans
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Receptors, G-Protein-Coupled / antagonists & inhibitors*
  • U937 Cells

Substances

  • GPR183 protein, human
  • Receptors, G-Protein-Coupled
  • Calcium