Literature DB >> 17896821

Rapid identification of immunostimulatory alpha-galactosylceramides using synthetic combinatorial libraries.

Qian Li1, Rachel M Ndonye, Petr A Illarionov, Karl O A Yu, Elliot S Jerud, Kristine Diaz, Gabriel Bricard, Steven A Porcelli, Gurdyal S Besra, Young-Tae Chang, Amy R Howell.   

Abstract

Two 60+-membered libraries of alpha-galactosylceramides have been prepared by reactions between activated ester resins and two core, fully deprotected galactosylated sphingoid bases. The libraries were evaluated for their ability to stimulate CD1d-restricted NKT cells, using in vitro stimulation of a murine NKT cell hybridoma line and for their ability to induce the expansion of NKT cells from peripheral blood mononuclear cells (PBMC) of a normal human subject. Our results showed that many compounds constructed on a C18-phytosphingosine base had significant stimulatory activity in both assays. Because no product purification was required, this approach is particularly attractive as a method for rapid synthesis of large libraries of potential immunomodulatory glycosylceramides.

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Year:  2007        PMID: 17896821     DOI: 10.1021/cc070057i

Source DB:  PubMed          Journal:  J Comb Chem        ISSN: 1520-4766


  10 in total

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2.  The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose.

Authors:  Zhenxing Zhang; Wei Zhao; Bin Wang; Chengfeng Xia; Wenpeng Zhang; Peng George Wang
Journal:  Org Lett       Date:  2011-08-04       Impact factor: 6.005

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Authors:  Ravinder Raju; Bernard F Castillo; Stewart K Richardson; Meena Thakur; Ryan Severins; Mitchell Kronenberg; Amy R Howell
Journal:  Bioorg Med Chem Lett       Date:  2009-06-06       Impact factor: 2.823

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

Authors:  Geetha Velmourougane; Ravinder Raju; Gabriel Bricard; Jin S Im; Gurdyal S Besra; Steven A Porcelli; Amy R Howell
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Review 5.  Glycolipid activators of invariant NKT cells as vaccine adjuvants.

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Journal:  Immunogenetics       Date:  2016-07-05       Impact factor: 2.846

6.  C-Galactosylceramide Diastereomers via Sharpless Asymmetric Epoxidation Chemistry.

Authors:  Jun Pu; Richard W Franck
Journal:  Tetrahedron       Date:  2008-09-08       Impact factor: 2.457

7.  Α-galactosylceramide analogs with weak agonist activity for human iNKT cells define new candidate anti-inflammatory agents.

Authors:  Gabriel Bricard; Manjunatha M Venkataswamy; Karl O A Yu; Jin S Im; Rachel M Ndonye; Amy R Howell; Natacha Veerapen; Petr A Illarionov; Gurdyal S Besra; Qian Li; Young-Tae Chang; Steven A Porcelli
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8.  Synthesis of amino core compounds of galactosyl phytosyl ceramide analogs for developing iNKT-cell inducers.

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Journal:  Molecules       Date:  2012-03-12       Impact factor: 4.411

9.  Kinetics and cellular site of glycolipid loading control the outcome of natural killer T cell activation.

Authors:  Jin S Im; Pooja Arora; Gabriel Bricard; Alberto Molano; Manjunatha M Venkataswamy; Ian Baine; Elliot S Jerud; Michael F Goldberg; Andres Baena; Karl O A Yu; Rachel M Ndonye; Amy R Howell; Weiming Yuan; Peter Cresswell; Young-Tae Chang; Petr A Illarionov; Gurdyal S Besra; Steven A Porcelli
Journal:  Immunity       Date:  2009-06-19       Impact factor: 31.745

10.  Synthesis and structure-activity relationships of cerebroside analogues as substrates of cerebroside sulphotransferase and discovery of a competitive inhibitor.

Authors:  Wenjin Li; Joren Guillaume; Younis Baqi; Isabell Wachsmann; Volkmar Gieselmann; Serge Van Calenbergh; Christa E Müller
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

  10 in total

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