Fluoro analogs of bioactive oxy-sterols: Synthesis of an EBI2 agonist with enhanced metabolic stability. Issue 20 (15th October 2016)

• Record Type: Journal Article
• Authors: Deng, Xiaohu; Sun, Siquan; Wu, Jiejun; Kuei, Chester; Joseph, Victory; Liu, Changlu; Mani, Neelakandha S.
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 20(2016)
• Page Start: 4888
• Page End: 4891
• Publication Date: 2016-10-15
• Subjects: Oxysterols -- Fluoro oxysterol -- Immune response -- Epstein–Barr virus -- GPR 183 -- EBI2 agonist; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2016.09.029
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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 oxysterol12 showed good metabolic stability while maintaining excellent EBI2 agonist activity. Abstract: 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 oxysterol12 showed good metabolic stability while maintaining excellent EBI2 agonist activity.