Literature DB >> 18586489

Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand.

Jeong-Ju Park1, Ji Hyung Lee, Subhash C Ghosh, Gabriel Bricard, Manjunatha M Venkataswamy, Steven A Porcelli, Sung-Kee Chung.   

Abstract

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined.

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Year:  2008        PMID： 18586489      PMCID： PMC2754801          DOI： 10.1016/j.bmcl.2008.06.036

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


  28 in total

1.  Total synthesis of alpha-galactosyl cerebroside.

Authors:  S Figueroa-Pérez; R R Schmidt
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2.  Synthesis and NKT cell stimulating properties of fluorophore- and biotin-appended 6"-amino-6"-deoxy-galactosylceramides.

Authors:  Xiao-Ti Zhou; Claire Forestier; Randal D Goff; Chunhong Li; Luc Teyton; Albert Bendelac; Paul B Savage
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

3.  Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells.

Authors:  Randal D Goff; Ying Gao; Jochen Mattner; Dapeng Zhou; Ning Yin; Carlos Cantu; Luc Teyton; Albert Bendelac; Paul B Savage
Journal:  J Am Chem Soc       Date:  2004-10-27       Impact factor: 15.419

4.  A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells.

Authors:  K Miyamoto; S Miyake; T Yamamura
Journal:  Nature       Date:  2001-10-04       Impact factor: 49.962

5.  Divergent syntheses of all stereoisomers of phytosphingosine and their use in the construction of a ceramide library.

Authors:  Jeong-Ju Park; Ji Hyung Lee; Qian Li; Kristine Diaz; Young-Tae Chang; Sung-Kee Chung
Journal:  Bioorg Chem       Date:  2008-02-14       Impact factor: 5.275

6.  Synthesis of alpha-galactosyl ceramide, a potent immunostimulatory agent.

Authors:  Oliver Plettenburg; Vera Bodmer-Narkevitch; Chi-Huey Wong
Journal:  J Org Chem       Date:  2002-06-28       Impact factor: 4.354

7.  The T cell antigen receptor expressed by Valpha14i NKT cells has a unique mode of glycosphingolipid antigen recognition.

Authors:  Stéphane Sidobre; Kirsten J L Hammond; Lise Bénazet-Sidobre; Sergei D Maltsev; Stewart K Richardson; Rachel M Ndonye; Amy R Howell; Teruyuki Sakai; Gurdyal S Besra; Steven A Porcelli; Mitchell Kronenberg
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-10       Impact factor: 11.205

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

Authors:  M Morita; K Motoki; K Akimoto; T Natori; T Sakai; E Sawa; K Yamaji; Y Koezuka; E Kobayashi; H Fukushima
Journal:  J Med Chem       Date:  1995-06-09       Impact factor: 7.446

9.  CD1-restricted NK T cells protect nonobese diabetic mice from developing diabetes.

Authors:  B Wang; Y B Geng; C R Wang
Journal:  J Exp Med       Date:  2001-08-06       Impact factor: 14.307

10.  Natural killer T cell activation inhibits hepatitis B virus replication in vivo.

Authors:  K Kakimi; L G Guidotti; Y Koezuka; F V Chisari
Journal:  J Exp Med       Date:  2000-10-02       Impact factor: 14.307
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  11 in total

1.  Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

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

Review 3.  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

4.  Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells.

Authors:  Barbara A Sullivan; Niranjana A Nagarajan; Gerhard Wingender; Jing Wang; Iain Scott; Moriya Tsuji; Richard W Franck; Steven A Porcelli; Dirk M Zajonc; Mitchell Kronenberg
Journal:  J Immunol       Date:  2009-11-30       Impact factor: 5.422

Review 5.  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

6.  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

Review 7.  Role of Innate T Cells in Anti-Bacterial Immunity.

Authors:  Yifang Gao; Anthony P Williams
Journal:  Front Immunol       Date:  2015-06-11       Impact factor: 7.561

Review 8.  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

9.  NKT cell-dependent glycolipid-peptide vaccines with potent anti-tumour activity.

Authors:  Regan J Anderson; Benjamin J Compton; Ching-Wen Tang; Astrid Authier-Hall; Colin M Hayman; Gene W Swinerd; Renata Kowalczyk; Paul Harris; Margaret A Brimble; David S Larsen; Olivier Gasser; Robert Weinkove; Ian F Hermans; Gavin F Painter
Journal:  Chem Sci       Date:  2015-06-25       Impact factor: 9.825

Review 10.  The versatility of the αβ T-cell antigen receptor.

Authors:  Mugdha Bhati; David K Cole; James McCluskey; Andrew K Sewell; Jamie Rossjohn
Journal:  Protein Sci       Date:  2014-01-28       Impact factor: 6.725
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