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

Behar, 2007, CD1-restricted T cells in host defense to infectious diseases, Curr Top Microbiol Immunol, 314, 215, 10.1007/978-3-540-69511-0_9 Wu, 2009, Natural killer T cells and autoimmune disease, Curr Mol Med, 9, 4, 10.2174/156652409787314534 Terabe, 2008, The role of NKT cells in tumor immunity, Adv Cancer Res, 101, 277, 10.1016/S0065-230X(08)00408-9 Godfrey, 2004, NKT cells: what's in a name?, Nat Rev Immunol, 4, 231, 10.1038/nri1309 Bricard, 2007, Antigen presentation by CD1 molecules and the generation of lipid-specific T cell immunity, Cell Mol Life Sci, 64, 1824, 10.1007/s00018-007-7007-0 Bendelac, 2007, The biology of NKT cells, Ann Rev Immunol, 25, 297, 10.1146/annurev.immunol.25.022106.141711 Matsuda, 2001, Natural killer T cells reactive to a single glycolipid exhibit a highly diverse T cell receptor beta repertoire and small clone size, Proc Natl Acad Sci USA, 98, 12636, 10.1073/pnas.221445298 Matsuda, 2002, Homeostasis of Vα14i NKT cells, Nat Immunol, 3, 966, 10.1038/ni837 Bendelac, 2001, Autoreactivity by design: innate B and T lymphocytes, Nat Rev Immunol, 1, 177, 10.1038/35105052 Yu, 2005, The diverse functions of CD1d-restricted NKT cells and their potential for immunotherapy, Immunol Lett, 100, 42, 10.1016/j.imlet.2005.06.010 Jiang, 2007, Mechanism of NKT cell-mediated transplant tolerance, Am J Transpl, 7, 1482, 10.1111/j.1600-6143.2007.01827.x Im, 2006, Expression of CD1d molecules by human schwann cells and potential interactions with immunoregulatory invariant NK T cells, J Immunol, 177, 5226, 10.4049/jimmunol.177.8.5226 Sakuishi, 2007, Invariant NKT cells biased for IL-5 production act as crucial regulators of inflammation, J Immunol, 179, 3452, 10.4049/jimmunol.179.6.3452 Brigl, 2003, Mechanism of CD1d-restricted natural killer T cell activation during microbial infection, Nat Immunol, 4, 1230, 10.1038/ni1002 Uldrich, 2005, NKT cell stimulation with glycolipid antigen in vivo: costimulation-dependent expansion, Bim-dependent contraction, and hyporesponsiveness to further antigenic challenge, J Immunol, 175, 3092, 10.4049/jimmunol.175.5.3092 Stetson, 2003, Constitutive cytokine mRNAs mark natural killer (NK) and NK T cells poised for rapid effector function, J Exp Med, 198, 1069, 10.1084/jem.20030630 Crowe, 2005, Differential antitumor immunity mediated by NKT cell subsets in vivo, J Exp Med, 202, 1279, 10.1084/jem.20050953 Cerundolo, 2009, Harnessing invariant NKT cells in vaccination strategies, Nat Rev Immunol, 9, 28, 10.1038/nri2451 Venkataswamy, 2009, Incorporation of NKT cell-activating glycolipids enhances immunogenicity and vaccine efficacy of Mycobacterium bovis Bacillus Calmette-Guerin, J Immunol, 183, 1644, 10.4049/jimmunol.0900858 Dondji, 2008, Intradermal NKT cell activation during DNA priming in heterologous prime-boost vaccination enhances T cell responses and protection against Leishmania, Eur J Immunol, 38, 706, 10.1002/eji.200737660 Kopecky-Bromberg, 2009, α-C-galactosylceramide as an adjuvant for a live attenuated influenza virus vaccine, Vaccine, 27, 3766, 10.1016/j.vaccine.2009.03.090 Bendelac, 1995, CD1 Recognition by mouse NK1+ T-lymphocytes, Science, 268, 863, 10.1126/science.7538697 Exley, 1997, Requirements for CD1d recognition by human invariant Vα24+ CD4−CD8− T cells, J Exp Med, 186, 109, 10.1084/jem.186.1.109 Cohen, 2009, Lipids, T cells, and NKT cells in microbial immunity, Adv Immunol, 102, 1, 10.1016/S0065-2776(09)01201-2 Joyce, 1998, Natural ligand of mouse CD1d1: cellular glycosylphosphatidylinositol, Science, 279, 1541, 10.1126/science.279.5356.1541 Yuan, 2009, Natural lipid ligands associated with human CD1d targeted to different subcellular compartments, J Immunol, 182, 4784, 10.4049/jimmunol.0803981 Gumperz, 2000, Murine CD1d-restricted T cell recognition of cellular lipids, Immunity, 12, 211, 10.1016/S1074-7613(00)80174-0 Rauch, 2003, Structural features of the acyl chain determine self-phospholipid antigen recognition by a CD1d-restricted invariant NKT (iNKT) cell, J Biol Chem, 278, 47508, 10.1074/jbc.M308089200 Chang, 2008, Inflammation-associated lysophospholipids as ligands for CD1d-restricted T cells in human cancer, Blood, 112, 1308, 10.1182/blood-2008-04-149831 Stanic, 2003, Defective presentation of the CD1d1-restricted natural Vα14Jα18 NKT lymphocyte antigen caused by β-d-glucosylceramide synthase deficiency, Proc Natl Acad Sci USA, 100, 1849, 10.1073/pnas.0430327100 Zhou, 2004, Lysosomal glycosphingolipid recognition by NKT cells, Science, 306, 1786, 10.1126/science.1103440 Chen, 2007, Synthesis and structure activity relationship study of isoglobotrihexosylceramide analogues, J Org Chem, 72, 9914, 10.1021/jo701539k Li, 2008, Sensitive quantitation of isoglobotriaosylceramide in the presence of isobaric components using electrospray ionization-ion trap mass spectrometry, Glycobiology, 18, 166, 10.1093/glycob/cwm127 Yin, 2009, Alpha anomers of iGb3 and Gb3 stimulate cytokine production by natural killer T cells, ACS Chem Biol, 4, 191, 10.1021/cb800277n Zajonc, 2008, Crystal structures of mouse CD1d-iGb3 complex and its cognate Vα14 T cell receptor suggest a model for dual recognition of foreign and self glycolipids, J Mol Biol, 377, 1104, 10.1016/j.jmb.2008.01.061 Gadola, 2006, Impaired selection of invariant natural killer T cells in diverse mouse models of glycosphingolipid lysosomal storage diseases, J Exp Med, 203, 2293, 10.1084/jem.20060921 Porubsky, 2007, Normal development and function of invariant natural killer T cells in mice with isoglobotrihexosylceramide (iGb3) deficiency, Proc Natl Acad Sci USA, 104, 5977, 10.1073/pnas.0611139104 Speak, 2007, Implications for invariant natural killer T cell ligands due to the restricted presence of isoglobotrihexosylceramide in mammals, Proc Natl Acad Sci USA, 104, 5971, 10.1073/pnas.0607285104 Wu, 2003, Cross-presentation of disialoganglioside GD3 to natural killer T cells, J Exp Med, 198, 173, 10.1084/jem.20030446 De Libero, 2007, Structure and biology of self lipid antigens, Curr Top Microbiol Immunol, 314, 51, 10.1007/978-3-540-69511-0_3 Jahng, 2004, Prevention of autoimmunity by targeting a distinct, noninvariant CD1d-reactive T cell population reactive to sulfatide, J Exp Med, 199, 947, 10.1084/jem.20031389 Zajonc, 2005, Structure and function of a potent agonist for the semi-invariant natural killer T cell receptor, Nat Immunol, 6, 810, 10.1038/ni1224 Fischer, 2004, Mycobacterial phosphatidylinositol mannoside is a natural antigen for CD1d-restricted T cells, Proc Natl Acad Sci USA, 101, 10685, 10.1073/pnas.0403787101 Kinjo, 2006, Natural killer T cells recognize diacylglycerol antigens from pathogenic bacteria, Nat Immunol, 7, 978, 10.1038/ni1380 Wu, 2005, Bacterial glycolipids and analogs as antigens for CD1d-restricted NKT cells, Proc Natl Acad Sci USA, 102, 1351, 10.1073/pnas.0408696102 Kinjo, 2005, Recognition of bacterial glycosphingolipids by natural killer T cells, Nature, 434, 520, 10.1038/nature03407 Mattner, 2005, Exogenous and endogenous glycolipid antigens activate NKT cells during microbial infections, Nature, 434, 525, 10.1038/nature03408 Kinjo, 2008, Natural Sphingomonas glycolipids vary greatly in their ability to activate natural killer T cells, Chem Biol, 15, 654, 10.1016/j.chembiol.2008.05.012 Long, 2007, Synthesis and evaluation of stimulatory properties of Sphingomonadaceae glycolipids, Nat Chem Biol, 3, 559, 10.1038/nchembio.2007.19 Amprey, 2004, A subset of liver NK T cells is activated during Leishmania donovani infection by CD1d-bound lipophosphoglycan, J Exp Med, 200, 895, 10.1084/jem.20040704 Lotter, 2009, Natural killer T cells activated by a lipopeptidophosphoglycan from Entamoeba histolytica are critically important to control amebic liver abscess, PLoS Pathog, 5, e1000434, 10.1371/journal.ppat.1000434 Kawano, 1997, CD1d-restricted and TCR-mediated activation of Vα14 NKT cells by glycosylceramides, Science, 278, 1626, 10.1126/science.278.5343.1626 Kobayashi, 1995, KRN7000, a novel immunomodulator, and its antitumor activities, Oncol Res, 7, 529 Benlagha, 2000, In vivo identification of glycolipid antigen-specific T cells using fluorescent CD1d tetramers, J Exp Med, 191, 1895, 10.1084/jem.191.11.1895 Matsuda, 2000, Tracking the response of natural killer T cells to a glycolipid antigen using CD1d tetramers, J Exp Med, 192, 741, 10.1084/jem.192.5.741 Van Kaer, 2005, alpha-Galactosylceramide therapy for autoimmune diseases: prospects and obstacles, Nat Rev Immunol, 5, 31, 10.1038/nri1531 Miyamoto, 2001, A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells, Nature, 413, 531, 10.1038/35097097 Schmieg, 2003, Superior protection against malaria and melanoma metastases by a C-glycoside analogue of the natural killer T cell ligand α-galactosylceramide, J Exp Med, 198, 1631, 10.1084/jem.20031192 Goff, 2004, Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells, J Am Chem Soc, 126, 13602, 10.1021/ja045385q Yu, 2005, Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of α-galactosylceramides, Proc Natl Acad Sci USA, 102, 3383, 10.1073/pnas.0407488102 Fujio, 2006, Structure-based discovery of glycolipids for CD1d-mediated NKT cell activation: tuning the adjuvant versus immunosuppression activity, J Am Chem Soc, 128, 9022, 10.1021/ja062740z Trappeniers, 2008, 6′-Derivatised α-GalCer analogues capable of inducing strong CD1d-mediated Th1-biased NKT cell responses in mice, J Am Chem Soc, 130, 16468, 10.1021/ja8064182 Li, 2009, Identification of C-glycoside analogues that display a potent biological activity against murine and human invariant natural killer T cells, Immunology, 127, 216, 10.1111/j.1365-2567.2008.02943.x Oki, 2004, The clinical implication and molecular mechanism of preferential IL-4 production by modified glycolipid-stimulated NKT cells, J Clin Invest, 113, 1631, 10.1172/JCI200420862 Chang, 2007, Potent immune-modulating and anticancer effects of NKT cell stimulatory glycolipids, Proc Natl Acad Sci USA, 104, 10299, 10.1073/pnas.0703824104 Ndonye, 2005, Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH, J Org Chem, 70, 10260, 10.1021/jo051147h Sidobre, 2004, The T cell antigen receptor expressed by Vα14 iNKT cells has a unique mode of glycosphingolipid antigen recognition, Proc Natl Acad Sci USA, 101, 12254, 10.1073/pnas.0404632101 Lee, 2007, Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant α-GalCer, J Med Chem, 50, 585, 10.1021/jm061243q Fuhshuku, 2008, RCAI-8, 9, 18, 19, and 49–52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: their synthesis and bioactivity for mouse natural killer T cells to produce cytokines, Bioorg Med Chem, 16, 950, 10.1016/j.bmc.2007.10.008 Fan, 2005, Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes, Tetrahedron, 61, 1855, 10.1016/j.tet.2004.12.027 Trappeniers, 2008, Synthesis and in vitro evaluation of α-GalCer epimers, ChemMedChem, 3, 1061, 10.1002/cmdc.200800021 Park, 2008, Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand, Bioorg Med Chem Lett, 18, 3906, 10.1016/j.bmcl.2008.06.036 Im, 2009, Kinetics and cellular site of glycolipid loading control the outcome of natural killer T cell activation, Immunity, 30, 888, 10.1016/j.immuni.2009.03.022 Parekh, 2004, Quantitative and qualitative differences in the in vivo response of NKT cells to distinct α- and β-anomeric glycolipids, J Immunol, 173, 3693, 10.4049/jimmunol.173.6.3693 Ortaldo, 2004, Dissociation of NKT stimulation, cytokine induction, and NK activation in vivo by the use of distinct TCR-binding ceramides, J Immunol, 172, 943, 10.4049/jimmunol.172.2.943 Prigozy, 2001, Glycolipid antigen processing for presentation by CD1d molecules, Science, 291, 664, 10.1126/science.291.5504.664 Tashiro, 2008, RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce Interferon-γ in vivo, Tetrahedron Lett, 49, 6827, 10.1016/j.tetlet.2008.09.074 Liu, 2006, A modified α-galactosyl ceramide for staining and stimulating natural killer T cells, J Immunol Meth, 312, 34, 10.1016/j.jim.2006.02.009 Reddy, 2009, Nonglycosidic agonists of invariant NKT cells for use as vaccine adjuvants, ChemMedChem, 4, 171, 10.1002/cmdc.200800354 Zeng, 1997, Crystal structure of mouse CD1: an MHC-like fold with a large hydrophobic binding groove, Science, 277, 339, 10.1126/science.277.5324.339 Koch, 2005, The crystal structure of human CD1d with and without α-galactosylceramide, Nat Immunol, 6, 819, 10.1038/ni1225 Zajonc, 2005, Structural basis for CD1d presentation of a sulfatide derived from myelin and its implications for autoimmunity, J Exp Med, 202, 1517, 10.1084/jem.20051625 Wu, 2006, Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d, Proc Natl Acad Sci USA, 103, 3972, 10.1073/pnas.0600285103 Borg, 2007, CD1d-lipid–antigen recognition by the semi-invariant NKT T-cell receptor, Nature, 448, 44, 10.1038/nature05907 Zajonc, 2006, Structural characterization of mycobacterial phosphatidylinositol mannoside binding to mouse CD1d, J Immunol, 177, 4577, 10.4049/jimmunol.177.7.4577 Forestier, 2007, Improved outcomes in NOD mice treated with a novel Th2 cytokine-biasing NKT cell activator, J Immunol, 178, 1415, 10.4049/jimmunol.178.3.1415 McCarthy, 2007, The length of lipids bound to human CD1d molecules modulates the affinity threshold of NKT cell activation, J Exp Med, 204, 1131, 10.1084/jem.20062342 van den Elzen, 2005, Apolipoprotein-mediated pathways of lipid antigen presentation, Nature, 437, 906, 10.1038/nature04001 Winau, 2004, Saposin C is required for lipid presentation by human CD1b, Nat Immunol, 5, 169, 10.1038/ni1035 Kang, 2004, Saposins facilitate CD1d-restricted presentation of an exogenous lipid antigen to T cells, Nat Immunol, 5, 175, 10.1038/ni1034 Yuan, 2007, Saposin B is the dominant saposin that facilitates lipid binding to human CD1d molecules, Proc Natl Acad Sci USA, 104, 5551, 10.1073/pnas.0700617104 Zhou, 2004, Editing of CD1d-bound lipid antigens by endosomal lipid transfer proteins, Science, 303, 523, 10.1126/science.1092009 Bai, 2009, Lysosomal recycling terminates CD1d-mediated presentation of short and polyunsaturated variants of the NKT cell lipid antigen alphaGalCer, Proc Natl Acad Sci USA, 106, 10254, 10.1073/pnas.0901228106 Bezbradica, 2005, Distinct roles of dendritic cells and B cells in Vα14Jα18 natural T cell activation in vivo, J Immunol, 174, 4696, 10.4049/jimmunol.174.8.4696 Lang, 2004, Presentation of α-galactosylceramide by murine CD1d to natural killer T cells is facilitated by plasma membrane glycolipid rafts, Immunology, 112, 386, 10.1111/j.1365-2567.2004.01896.x Park, 2005, Lipid rafts are required for efficient signal transduction by CD1d, Biochem Biophys Res Commun, 327, 1143, 10.1016/j.bbrc.2004.12.121 Peng, 2007, Influence of lipid rafts on CD1d presentation by dendritic cells, Mol Membr Biol, 24, 475, 10.1080/09687680701359408 Buatois, 2003, MHC class II-peptide complexes in dendritic cell lipid microdomains initiate the CD4 Th1 phenotype, J Immunol, 171, 5812, 10.4049/jimmunol.171.11.5812