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Bioorg Med Chem Lett. 2012 Jul 1;22(13):4348-52. doi: 10.1016/j.bmcl.2012.05.009. Epub 2012 May 9.

New CD1d agonists: synthesis and biological activity of 6″-triazole-substituted α-galactosyl ceramides.

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  • 1School of Biosciences, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.

Abstract

Huisgen [3+2] dipolar cycloaddition of 6″-azido-6″-deoxy-α-galactosyl ceramide 11 with a range of alkynes (or a benzyne precursor) yielded a series of triazole-containing α-galactosyl ceramide (α-GalCer) analogues in high yield. These α-GalCer analogues and the precursor azide 11 were tested for their ability to activate iNKT cells and stimulate IL-2 cytokine secretion in vitro, and IFN-γ and IL-4 cytokine secretion in vivo. Some of these analogues, specifically 11, 12b, 12f and 13, were more potent IL-2 stimulators than the prototypical CD1d agonist, α-GalCer 1. In terms of any cytokine bias, most of the triazole-containing analogues exhibited a small Th2 cytokine-biasing response relative to that shown by α-GalCer 1. In contrast, the cycloaddition precursor, namely azide 11, provided a small Th1 cytokine-biasing response.

PMID:
22652050
PMCID:
PMC3401990
DOI:
10.1016/j.bmcl.2012.05.009
[PubMed - indexed for MEDLINE]
Free PMC Article
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