Literature DB >> 18418814

Synthesis and in vitro evaluation of alpha-GalCer epimers.

Matthias Trappeniers1, Stijn Goormans, Katrien Van Beneden, Tine Decruy, Bruno Linclau, Aymen Al-Shamkhani, Tim Elliott, Christian Ottensmeier, Joern M Werner, Dirk Elewaut, Serge Van Calenbergh.   

Abstract

alpha-GalCer (also known as KRN7000) is an immunomodulatory glycolipid that is known to potently activate invariant natural killer T (NKT) cells upon CD1d-mediated stimulation. Because Th1 and Th2 cytokines, which are released after alpha-GalCer presentation, antagonize each other's effects, alpha-GalCer analogues that induce a biased Th1/Th2 response are highly awaited. In this context, we report the synthesis and in vitro evaluation of alpha-Gal-D-xylo-Cer and two alpha-Gal-L-lyxo-Cer analogues, one with the natural acyl chain, the other with a truncated chain.

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Year:  2008        PMID： 18418814     DOI： 10.1002/cmdc.200800021

Source DB:  PubMed          Journal:  ChemMedChem        ISSN： 1860-7179            Impact factor:   3.466


  10 in total

Review 1.  Raising the roof: the preferential pharmacological stimulation of Th1 and th2 responses mediated by NKT cells.

Authors:  James E East; Andrew J Kennedy; Tonya J Webb
Journal:  Med Res Rev       Date:  2012-12-13       Impact factor: 12.944

2.  The 3-Deoxy Analogue of α-GalCer: Disclosing the Role of the 4-Hydroxyl Group for CD1d-Mediated NKT Cell Activation.

Authors:  Dong Jae Baek; Jeong-Hwan Seo; Chaemin Lim; Jae Hyun Kim; Doo Hyun Chung; Won-Jea Cho; Chang-Yuil Kang; Sanghee Kim
Journal:  ACS Med Chem Lett       Date:  2011-05-16       Impact factor: 4.345

3.  Synthesis and evaluation of amino-modified alpha-GalCer analogues.

Authors:  Matthias Trappeniers; René Chofor; Sandrine Aspeslagh; Yali Li; Bruno Linclau; Dirk M Zajonc; Dirk Elewaut; Serge Van Calenbergh
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

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

Authors:  Kun-Hsien Lin; Jian-Jong Liang; Wen-I Huang; Shao-Ying Lin-Chu; Ching-Yao Su; Yi-Ling Lee; Jia-Tsong Jan; Yi-Ling Lin; Yih-Shyun E Cheng; Chi-Huey Wong
Journal:  Antimicrob Agents Chemother       Date:  2010-07-26       Impact factor: 5.191

5.  The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.

Authors:  Ahmad S Altiti; Stewart Bachan; David R Mootoo
Journal:  Org Lett       Date:  2016-08-25       Impact factor: 6.005

Review 6.  Lipid and glycolipid antigens of CD1d-restricted natural killer T cells.

Authors:  Manjunatha M Venkataswamy; Steven A Porcelli
Journal:  Semin Immunol       Date:  2009-11-27       Impact factor: 11.130

7.  Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry.

Authors:  Jeong-Ju Park; Ji Hyung Lee; Kyung-Chang Seo; Gabriel Bricard; Manjunatha M Venkataswamy; Steven A Porcelli; Sung-Kee Chung
Journal:  Bioorg Med Chem Lett       Date:  2010-01-04       Impact factor: 2.823

8.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962

Review 9.  Stimulation of natural killer T cells by glycolipids.

Authors:  Brian L Anderson; Luc Teyton; Albert Bendelac; Paul B Savage
Journal:  Molecules       Date:  2013-12-16       Impact factor: 4.411

Review 10.  Antigen specificity of invariant natural killer T-cells.

Authors:  Alysia M Birkholz; Mitchell Kronenberg
Journal:  Biomed J       Date:  2016-03-10       Impact factor: 4.910
  10 in total

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