Fluoro analogs of bioactive oxy-sterols: Synthesis of an EBI2 agonist with enhanced metabolic stability

Bioorg Med Chem Lett. 2016 Oct 15;26(20):4888-4891. doi: 10.1016/j.bmcl.2016.09.029. Epub 2016 Sep 12.


Synthesis of several 7-hydroxy oxysterols and their potential roles as signaling molecules in the innate and adaptive immune responses is discussed. Discovery of a new, fluorinated, synthetic analog of the 7α,25-dihydroxycholesterol-the endogenous ligand of GPR 183 (EBI2), a G-protein coupled receptor highly expressed upon Epstein-Barr virus infection is described. Fluoro oxysterol 12 showed good metabolic stability while maintaining excellent EBI2 agonist activity.

Keywords: EBI2 agonist; Epstein–Barr virus; Fluoro oxysterol; GPR 183; Immune response; Oxysterols.

MeSH terms

  • Animals
  • Cell Line
  • Herpesvirus 4, Human / drug effects
  • Herpesvirus 4, Human / metabolism
  • Humans
  • Oxysterols / chemical synthesis
  • Oxysterols / chemistry*
  • Oxysterols / pharmacology
  • Receptors, G-Protein-Coupled / metabolism


  • Oxysterols
  • Receptors, G-Protein-Coupled