Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation.

Natacha Veerapen, F Reddington, M Salio, V Cerundolo, Gurdyal Besra

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Stimulation of iNKT cells by α-galactosyl ceramide (α-GalCer), also known as KRN7000, and its truncated analogue OCH induces both Th1- and Th2-cytokines, with OCH inducing a Th2-cytokine bias. Skewing of the iNKT cells' response towards either a Th1- or Th2-cytokine profile offers potential therapeutic benefits. The length of both the acyl and the sphingosine chains in α-galactosyl ceramides is known to influence the cytokine release profile. We have synthesized analogues of α-GalCer with truncated sphingosine chains for biological evaluation, with particular emphasis on the Th1/Th2 distribution. Starting from a common precursor, d-lyxose, the sphingosine derivatives were synthesised via a straightforward Wittig condensation.
Original languageEnglish
Pages (from-to)221-8
Number of pages8
JournalBioorganic & Medicinal Chemistry
Volume19
Issue number1
DOIs
Publication statusPublished - 1 Jan 2011

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