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Literature DB >> 22408579

C-Galactosylceramide: Synthesis and Immunology.

Abstract

A synthetic C-glycoside, α-C-galactosylceramide, is an active immunostimulant in mice. It displays better activity than α-O-galactosylceramide in several disease models. Syntheses of several α-C-galactosylceramides are described. Experiments that probe its immunostimulant activity are outlined. Possible explanations for its superior activity are discussed.

Entities: Chemical Disease Gene Species

Year: 2012 PMID： 22408579 PMCID： PMC3293403 DOI： 10.1016/j.crci.2011.05.006

Source DB: PubMed Journal: C R Chim ISSN： 1631-0748 Impact factor: 3.117

39 in total

Review 1. Toward an understanding of NKT cell biology: progress and paradoxes.

Authors: Mitchell Kronenberg
Journal: Annu Rev Immunol Date: 2005 Impact factor: 28.527

2. Synthesis and growth inhibitory properties of glucosamine-derived glycerolipids.

Authors: G Yang; R W Franck; R Bittman; P Samadder; G Arthur
Journal: Org Lett Date: 2001-01-25 Impact factor: 6.005

3. Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.

Authors: Tetsuya Toba; Kenji Murata; Kyoko Nakanishi; Bitoku Takahashi; Naohiro Takemoto; Minako Akabane; Takashi Nakatsuka; Seiichi Imajo; Takashi Yamamura; Sachiko Miyake; Hirokazu Annoura
Journal: Bioorg Med Chem Lett Date: 2007-03-03 Impact factor: 2.823

4. Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

Authors: Peter Wipf; Joshua G Pierce
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

5. Eradication of solid tumors using histone deacetylase inhibitors combined with immune-stimulating antibodies.

Authors: Ailsa J Christiansen; Alison West; Kellie-Marie Banks; Nicole M Haynes; Michele W Teng; Mark J Smyth; Ricky W Johnstone
Journal: Proc Natl Acad Sci U S A Date: 2011-02-22 Impact factor: 11.205

6. Influenza infection in suckling mice expands an NKT cell subset that protects against airway hyperreactivity.

Authors: Ya-Jen Chang; Hye Young Kim; Lee A Albacker; Hyun Hee Lee; Nicole Baumgarth; Shizuo Akira; Paul B Savage; Shin Endo; Takashi Yamamura; Janneke Maaskant; Naoki Kitano; Abel Singh; Apoorva Bhatt; Gurdyal S Besra; Peter van den Elzen; Ben Appelmelk; Richard W Franck; Guangwu Chen; Rosemarie H DeKruyff; Michio Shimamura; Petr Illarionov; Dale T Umetsu
Journal: J Clin Invest Date: 2010-12-13 Impact factor: 14.808

7. Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

Authors: Guangwu Chen; John Schmieg; Moriya Tsuji; Richard W Franck
Journal: Org Lett Date: 2004-10-28 Impact factor: 6.005

8. Stereoselective synthesis of alpha- and beta-L-C-fucosyl aldehydes and their utility in the assembly of C-fucosides of biological relevance.

Authors: Alessandro Dondoni; Nicola Catozzi; Alberto Marra
Journal: J Org Chem Date: 2004-07-23 Impact factor: 4.354

9. Invariant TCR rather than CD1d shapes the preferential activities of C-glycoside analogues against human versus murine invariant NKT cells.

Authors: Xiangming Li; Takayuki Shiratsuchi; Guangwu Chen; Paolo Dellabona; Giulia Casorati; Richard W Franck; Moriya Tsuji
Journal: J Immunol Date: 2009-09-04 Impact factor: 5.422

C-Galactosylceramide: Synthesis and Immunology.

Review 1. Toward an understanding of NKT cell biology: progress and paradoxes.

2. Synthesis and growth inhibitory properties of glucosamine-derived glycerolipids.

3. Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs.

4. Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

5. Eradication of solid tumors using histone deacetylase inhibitors combined with immune-stimulating antibodies.

6. Influenza infection in suckling mice expands an NKT cell subset that protects against airway hyperreactivity.

7. Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

8. Stereoselective synthesis of alpha- and beta-L-C-fucosyl aldehydes and their utility in the assembly of C-fucosides of biological relevance.

9. Invariant TCR rather than CD1d shapes the preferential activities of C-glycoside analogues against human versus murine invariant NKT cells.

10. A multifactorial mechanism in the superior antimalarial activity of alpha-C-GalCer.

1. Synthesis and biological activities of C-glycosides of KRN 7000 with novel ceramide residues.

2. Design, Synthesis, and Immunological Evaluation of Benzyloxyalkyl-Substituted 1,2,3-Triazolyl α-GalCer Analogues.

3. Synthesis and Immunological Activity of Novel Oligo(ethylene glycol) Analogues of α-Galactosylceramide.

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