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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 publication

DOI

10.1016/j.bmc.2010.11.032

Type

Journal article

Journal

Bioorg Med Chem

Publication Date

01/01/2011

Volume

19

Pages

221 - 228

Keywords

Cytokines, Drug Evaluation, Preclinical, Galactosylceramides, Humans, Killer Cells, Natural, T-Lymphocytes