Literature DB >> 19481452

Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH.

Geetha Velmourougane1, Ravinder Raju, Gabriel Bricard, Jin S Im, Gurdyal S Besra, Steven A Porcelli, Amy R Howell.   

Abstract

An alpha-galactosyl ceramide (alpha-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKT-cell proliferation and elicit T-helper cytokines, IL-4 and IFNgamma. Compound 2 combines the acyl chain of the potent, Th2 biasing alpha-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related alpha-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison.

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Year:  2009        PMID: 19481452      PMCID: PMC2743301          DOI: 10.1016/j.bmcl.2009.05.042

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  15 in total

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Journal:  Proc Natl Acad Sci U S A       Date:  2005-02-18       Impact factor: 11.205

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Review 9.  CD1-restricted T cells and tumor immunity.

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10.  Structure-activity relationship of alpha-galactosylceramides against B16-bearing mice.

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  9 in total

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3.  In vivo protection provided by a synthetic new alpha-galactosyl ceramide analog against bacterial and viral infections in murine models.

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5.  Regulation of the actin cytoskeleton by Rho kinase controls antigen presentation by CD1d.

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

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Review 7.  Stimulation of natural killer T cells by glycolipids.

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8.  Relationships between Th1 or Th2 iNKT cell activity and structures of CD1d-antigen complexes: meta-analysis of CD1d-glycolipids dynamics simulations.

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  9 in total

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