Literature DB >> 18006319

Glycolipids as immunostimulating agents.

Douglass Wu1, Masakazu Fujio, Chi-Huey Wong.   

Abstract

The processing and presentation of lipid antigens by antigen presenting cells (APC) is important for defense against infection, tumor immunosurveillance, and autoimmunity. CD1, a family of cell surface glycoproteins, is responsible for the binding and presentation of lipid antigens to receptors expressed on the surface of T lymphocytes. Among the several (glyco)lipids identified to cause T-cell stimulation in complex with CD1, alpha-galactosyl ceramide (alpha-GalCer) is one of the most well studied. A combination of structure-activity relationship (SAR), crystallographic studies, and discovery of new 'natural' antigens has led to greater understanding of the structural requirements for optimal natural killer T-cell activation.

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Year:  2007        PMID: 18006319      PMCID: PMC2279229          DOI: 10.1016/j.bmc.2007.10.026

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  78 in total

1.  Detection of sphingomonads and in situ identification in activated sludge using 16S rRNA-targeted oligonucleotide probes.

Authors:  A Neef; R Witzenberger; P Kämpfer
Journal:  J Ind Microbiol Biotechnol       Date:  1999-10       Impact factor: 3.346

2.  Structural features of the acyl chain determine self-phospholipid antigen recognition by a CD1d-restricted invariant NKT (iNKT) cell.

Authors:  Joyce Rauch; Jenny Gumperz; Cheryl Robinson; Markus Sköld; Chris Roy; David C Young; Michel Lafleur; D Branch Moody; Michael B Brenner; Catherine E Costello; Samuel M Behar
Journal:  J Biol Chem       Date:  2003-09-08       Impact factor: 5.157

3.  Two classes of CD1 genes.

Authors:  F Calabi; J M Jarvis; L Martin; C Milstein
Journal:  Eur J Immunol       Date:  1989-02       Impact factor: 5.532

4.  Natural killer-like nonspecific tumor cell lysis mediated by specific ligand-activated Valpha14 NKT cells.

Authors:  T Kawano; J Cui; Y Koezuka; I Toura; Y Kaneko; H Sato; E Kondo; M Harada; H Koseki; T Nakayama; Y Tanaka; M Taniguchi
Journal:  Proc Natl Acad Sci U S A       Date:  1998-05-12       Impact factor: 11.205

Review 5.  Immunotherapeutic potential for ceramide-based activators of iNKT cells.

Authors:  Celia R Berkers; Huib Ovaa
Journal:  Trends Pharmacol Sci       Date:  2005-05       Impact factor: 14.819

6.  Sequential production of interferon-gamma by NK1.1(+) T cells and natural killer cells is essential for the antimetastatic effect of alpha-galactosylceramide.

Authors:  Mark J Smyth; Nadine Y Crowe; Daniel G Pellicci; Konstantinos Kyparissoudis; Janice M Kelly; Kazuyoshi Takeda; Hideo Yagita; Dale I Godfrey
Journal:  Blood       Date:  2002-02-15       Impact factor: 22.113

7.  Mycobacterial phosphatidylinositol mannoside is a natural antigen for CD1d-restricted T cells.

Authors:  Karsten Fischer; Emmanuel Scotet; Marcus Niemeyer; Heidrun Koebernick; Jens Zerrahn; Sophie Maillet; Robert Hurwitz; Mischo Kursar; Marc Bonneville; Stefan H E Kaufmann; Ulrich E Schaible
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-08       Impact factor: 11.205

Review 8.  Natural killer T cells as targets for immunotherapy of autoimmune diseases.

Authors:  Luc Van Kaer
Journal:  Immunol Cell Biol       Date:  2004-06       Impact factor: 5.126

9.  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

10.  Sustained expansion of NKT cells and antigen-specific T cells after injection of alpha-galactosyl-ceramide loaded mature dendritic cells in cancer patients.

Authors:  David H Chang; Keren Osman; John Connolly; Anjli Kukreja; Joseph Krasovsky; Maggi Pack; Aisha Hutchinson; Matthew Geller; Nancy Liu; Rebecca Annable; Jennifer Shay; Kelly Kirchhoff; Nobusuke Nishi; Yoshitaka Ando; Kunihiko Hayashi; Hani Hassoun; Ralph M Steinman; Madhav V Dhodapkar
Journal:  J Exp Med       Date:  2005-05-02       Impact factor: 14.307

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  28 in total

1.  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

2.  Synthesis and evaluation of 3''- and 4''-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000.

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

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.  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

5.  One-pot syntheses of immunostimulatory glycolipids.

Authors:  Matthew Schombs; Francine E Park; Wenjun Du; Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

6.  Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments.

Authors:  Hai-Lin Zhang; Xiao-Peng He; Li Sheng; Yuan Yao; Wei Zhang; Xiao-Xin Shi; Jia Li; Guo-Rong Chen
Journal:  Mol Divers       Date:  2011-06-05       Impact factor: 2.943

7.  Design and Evaluation of ω-Hydroxy Fatty Acids Containing α-GalCer Analogues for CD1d-Mediated NKT Cell Activation.

Authors:  Chaemin Lim; Jae Hyun Kim; Dong Jae Baek; Joo-Youn Lee; Minjae Cho; Yoon-Sook Lee; Chang-Yuil Kang; Doo Hyun Chung; Won-Jae Cho; Sanghee Kim
Journal:  ACS Med Chem Lett       Date:  2014-02-04       Impact factor: 4.345

8.  Heteroaromatic Moieties in the Sphingosine Backbone of α-Galactosylceramides for Noncovalent Interactions with CD1d.

Authors:  Yongju Kim; Jonghoon Kim; Keunhee Oh; Dong-Sup Lee; Seung Bum Park
Journal:  ACS Med Chem Lett       Date:  2012-01-10       Impact factor: 4.345

9.  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

10.  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

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