9 mmoles) est dissout dans du méthanol (250 ml), du méthanolate de sodium est ajouté au milieu réactionnel jusqu'à pH= 9-10 Après 1 heure sous agitation et à température ambiante, la réaction est traitée par ajout d'amberlite IR120 jusqu'à pH=7. Le mélange est filtré. Le filtrat récupéré est évaporé à sec ,
55 (d ; H1, J<1 Hz Hz, vol.4, issue.2, p.50 ,
43 mmole) est dissous dans un mélange THF/H 2 O (9ml/2ml) et la PPh 3 est ajouté (340 mg ; 1,29 mmoles) La réaction est agitée pendant 12 heures. Le solvant est évaporé sous pression réduite et le brut est chromatographié sur colonne de silice avec un mélange d'éluant CH 2 Cl 2 /MeOH mg, pp.466-95 ,
31,4086 (Cr ; Cm), CsCeCb, vol.387, issue.50, p.510824 ,
Le milieu est bullé pour permettre son dégazage grâce à l'utilisation d'un ballon de baudruche rempli d'argon. Une aiguille donnant sur l'extérieur permet aux vapeurs 124,56, Caro Cquat.CvCu, vol.55, issue.175, p.91154612146017, 1970. ,
mg95 µmoles) et de l'acide polyéthylène glycol (n=42) (22 mg, p.95 ,
168 mmole) est mis en solution dans 3 ml de THF, en présence de PPh 3 (133 mg ; 0,506 mmole) et de 40 µl d'H 2 O. Le mélange est agité pendant 24 heures à température ambiante. Le solvant est ensuite évaporé sous pression réduite ,
40 µl ; 0,18 mmole) sont dissous dans 2 ml de MeOH Au bout de 10 minutes, le Boc 2 O (24 mg ; 0,11 mmole) dissous préalablement dans 1 ml de MeOH, est ajouté au milieu réactionnel Après 4 heures d'agitation sous argon, le milieu est lavé avec H 2 O (10 ml) et une solution de saumure (10 ml) Puis la phase aqueuse est extraite par 3 x 10 ml de CH 2 Cl 2 . Les phases organiques sont rassemblées, séchées sur MgSO 4 et filtrées. Le mélange est séché et passé sur colonne de silice avec un éluant cyclohexane mg, pp.84-71 ,
Le milieu est bullé pour permettre son dégazage grâce à l'utilisation d'un ballon de baudruche rempli d'argon. Une aiguille donnant sur l'extérieur permet aux vapeurs de solvants d'être évacuées. On retire le ballon d'argon et on ajoute du Pd/C (120 mg) Le milieu est mis sous atmosphère d'H 2 à 60 psi pendant 3 jours Le Pd/C est filtré sur célite et lavé plusieurs fois avec du THF, puis par un mélange CH 2 Cl mg, La phase organique est évaporée séchée. Le résidu est déposé sur colonne de silice avec un éluant CH 2 Cl 2 /MeOH, p.60 ,
mg ; 0,014 mmole) est dissous dans 1 ml de CH 2 Cl 2 . A 0°C, on ajoute 1 ml de TFA. On laisse sous agitation et sous argon pendant 2 heures à température ambiante. Le milieu est évaporé à sec pour donner le sel de TFA ,
En parallèle, du Cy5-COOH est dissous dans 1 ml de CH 2 Cl 2 (9 mg ; 0,017 mmole), et du BOP (7 mg ; 0,017 mmole) est ajouté. Le milieu est laissé sous agitation pendant 10 minutes, puis le sel de TFA et la DIEA sont ajoutés. Le milieu est laissé une nuit sous agitation et sous argon, à l'abri de la lumière et à température ambiante mg, Le milieu est évaporé à sec et le résidu est chromatographié sur colonne de silice avec un mélange d'éluant CH 2 Cl 2 /MeOH, pp.14-86 ,
Syntheses of ???-monoglycosylcermaides and four diastereoisomers of an ?galactosylceramide, Bioorganic and Medicinal Chemistry Letters, issue.5, pp.699-704, 1995. ,
Antitumor cytotoxicity mediated by ligand-activated human V alpha24 NKT cells, Cancer Research, vol.59, pp.5102-5105, 1999. ,
Loss of IFN-?? Production by Invariant NK T Cells in Advanced Cancer, The Journal of Immunology, vol.167, issue.7, pp.4046-4050, 2001. ,
DOI : 10.4049/jimmunol.167.7.4046
Opinion: NKT cells: what's in a name?, Nature Reviews Immunology, vol.11, issue.3, pp.231-237, 2004. ,
DOI : 10.1038/nri1309
An invariant V alpha 24-J alpha Q/V beta 11 T cell receptor is expressed in all individuals by clonally expanded CD4-8- T cells, Journal of Experimental Medicine, vol.180, issue.3, pp.1171-1176, 1994. ,
DOI : 10.1084/jem.180.3.1171
CD1d-restricted Recognition of Synthetic Glycolipid Antigens by Human Natural Killer T Cells, The Journal of Experimental Medicine, vol.147, issue.8, pp.1529-1534, 1998. ,
DOI : 10.1093/intimm/8.11.1751
TOWARD AN UNDERSTANDING OF NKT CELL BIOLOGY: Progress and Paradoxes, Annual Review of Immunology, vol.23, issue.1, pp.877-900, 2005. ,
DOI : 10.1146/annurev.immunol.23.021704.115742
Cd4(Pos), Nk1.1(Pos) T-Cells Promptly Produce Interleukin-4 in Response to in-Vivo. Challenge with anti-CD3, Journal of Experimental Medicine, issue.179, pp.1285-1295, 1994. ,
Cutting edge: Cross-talk between cells of the innate immune system: NKT cells rapidly activate NK cells, Journal of Immunology, vol.163, pp.4647-4650, 1999. ,
Going both ways: Immune regulation via CD1d-dependent NKT cells, Journal of Clinical Investigation, vol.114, issue.10, pp.1379-1388, 2004. ,
DOI : 10.1172/JCI200423594
Natural killer T cells: rapid responders controlling immunity and disease, The International Journal of Biochemistry & Cell Biology, vol.37, issue.7, pp.1337-1343, 2005. ,
DOI : 10.1016/j.biocel.2004.11.019
The Biology of NKT Cells, Annual Review of Immunology, vol.25, issue.1, pp.297-336, 2007. ,
DOI : 10.1146/annurev.immunol.25.022106.141711
Developmentally regulated expression of T cell receptor beta chain variable domains in immature thymocytes, Journal of Experimental Medicine, vol.166, issue.2, pp.577-582, 1987. ,
DOI : 10.1084/jem.166.2.577
A novel population of T-cell receptor ????-bearing thymocytes which predominantly expresses a single V?? gene family, Nature, vol.329, issue.6136, pp.251-256, 1987. ,
DOI : 10.1038/329251a0
Phenotypic properties, interleukin 2 production, and developmental origin of a "mature" subpopulation of Lyt-2- L3T4- mouse thymocytes., Proceedings of the National Academy of Sciences, vol.84, issue.23, pp.8578-8582, 1987. ,
DOI : 10.1073/pnas.84.23.8578
Unsual T cell population in adult murine bone marrow. Prevalence of CD3, CD4-CD8-and ?? TCR NK1.1 cells, Journal of Immunology, issue.145, pp.3209-3215, 1990. ,
The fate of CD4-8-T cell receptor ?? thymocytes, Journal of Immunology, issue.146, pp.1113-1117, 1991. ,
Predominant expression of invariant Va14 TCR a-chain in NK1.1 T cell populations, International Immunollogy, issue.7, pp.1157-1161, 1995. ,
MOUSE CD1-SPECIFIC NK1 T CELLS: Development, Specificity, and Function, Annual Review of Immunology, vol.15, issue.1, pp.535-562, 1997. ,
DOI : 10.1146/annurev.immunol.15.1.535
Lipid antigen presentation in the immune system; lessons learned from CD 1 d knockout mice, Immunological Reviews, vol.25, issue.1, pp.31-44, 1999. ,
DOI : 10.1084/jem.189.1.103
Unaltered phenotype, tissue distribution and function of V??14+ NKT cells in germ-free mice, European Journal of Immunology, vol.30, issue.2, pp.620-625, 2000. ,
DOI : 10.1002/1521-4141(200002)30:2<620::AID-IMMU620>3.0.CO;2-4
Raising the NKT cell family, Nature Immunology, vol.172, issue.3, pp.197-206, 2010. ,
DOI : 10.1016/j.immuni.2006.06.017
NKT cell-mediated repression of tumor immunosurveillance by IL-13 and the IL-4R-STAT6 pathway, Nature Immunology, issue.1, pp.515-520, 2000. ,
Functionnaly distinct subsets of CD1d-restricted natural killer T cells revealed by CD1d tetramer staining, Journal of Experimental Medicine, pp.625-636, 0195. ,
A Thymic Precursor to the NK T Cell Lineage, Science, vol.296, issue.5567, pp.553-555, 2002. ,
DOI : 10.1126/science.1069017
A Natural Killer T (NKT) cell developpement pathway involving a thymusdependent NK1.1-CD4 CD1d-dependent precursor stage, Journal of Experimental Medicine, pp.835-844, 0195. ,
Glycolipid antigen drives rapid expansion and sustained cytokine production by NKT cells, Journal of Immunology, issue.171, pp.4020-4027, 2003. ,
The response of natural killer T cells to glycolipid antigens is characterized by surface receptor down-modulation and expansion, Proceedings of the National Academy of Sciences of the United States of America, pp.10913-10918, 2003. ,
DOI : 10.1073/pnas.1833166100
CD1-restricted CD4+ T cells in major histocompatibility complex class II-deficient mice, Journal of Experimental Medicine, vol.182, issue.4, pp.993-1004, 1995. ,
DOI : 10.1084/jem.182.4.993
NKT Cells in Tumor Immunity: Opposing Subsets Define a New Immunoregulatory Axis, The Journal of Immunology, vol.180, issue.6, pp.3627-3635, 2008. ,
DOI : 10.4049/jimmunol.180.6.3627
A nonclassical non-V??14J??18 CD1d-restricted (type II) NKT cell is sufficient for down-regulation of tumor immunosurveillance, The Journal of Experimental Medicine, vol.58, issue.12, pp.1627-1633, 2005. ,
DOI : 10.1172/JCI200419836
NKT cells are phenotypically and functionally diverse, European Journal of Immunology, vol.10, issue.11, pp.3768-3781, 1999. ,
DOI : 10.1002/(SICI)1521-4141(199911)29:11<3768::AID-IMMU3768>3.0.CO;2-G
Tissue specific segregation of CD1d-dependant and CD1d-independant NKT cells, Journal of Immunology, vol.162, pp.6410-6419, 1999. ,
CD1d and MR1-restricted invariant T cells: of mice and men. Current Opinion of Immunology, pp.519-526, 2006. ,
Chapter 1 Antigen Presentation by CD1, Advances in Immunology, vol.102, pp.1-94, 2009. ,
DOI : 10.1016/S0065-2776(09)01201-2
A semi-invariant V??10+ T cell antigen receptor defines a population of natural killer T cells with distinct glycolipid antigen???recognition properties, Nature Immunology, vol.276, issue.7, pp.616-625, 2011. ,
DOI : 10.1038/ni1224
CELL BIOLOGY OF ANTIGEN PROCESSING IN VITRO AND IN VIVO, Annual Review of Immunology, vol.23, issue.1 ,
DOI : 10.1146/annurev.immunol.22.012703.104538
Developmental regulation of MHC class II transport in mouse dendritic cells, Nature, vol.388, pp.787-792, 1997. ,
Dendritic-cell trafficking to lymph nodes through lymphatic vessels, Nature Reviews Immunology, vol.161, issue.8, pp.617-628, 2005. ,
DOI : 10.1038/ni962
The Linkage of Innate to Adaptive Immunity via Maturing Dendritic Cells In Vivo Requires CD40 Ligation in Addition to Antigen Presentation and CD80/86 Costimulation, The Journal of Experimental Medicine, vol.162, issue.12, pp.1607-1618, 0199. ,
DOI : 10.4049/jimmunol.167.11.6247
Dendritic cells and the control of immunity, Nature, vol.392, issue.6673, pp.245-252, 1998. ,
DOI : 10.1038/32588
Type-I interferon signaling in dendritic cells stimulates the development of lymph-noderesident T follicular helper cells, Immunity, pp.31-491, 2009. ,
Myeloid C-type lectins in innate immunity, Nature Immunology, vol.281, issue.12, pp.1258-1265, 2006. ,
DOI : 10.1074/jbc.M203774200
Plasmacytoid dendritic cells, antigen, and CpG-C license human B cells for plasma cell differentiation and immunoglobulin production in the absence of T-cell help, Blood, vol.103, issue.8, pp.3058-3064, 2004. ,
DOI : 10.1182/blood-2003-08-2972
A fresh look at tumor immunosurveillance and immunotherapy, Nature Immunology, issue.2, pp.293-299, 2001. ,
Structure and function of a potent agonist for the semi-invariant natural killer T cell receptor, Nature Immunology, vol.50, issue.8, pp.810-818, 2005. ,
DOI : 10.1093/intimm/13.7.853
Understanding the function of CD1-restricted T cells, Nature Immunology, vol.4, issue.6, pp.517-523, 2003. ,
DOI : 10.1038/ni0603-517
CD1: Antigen Presentation and T Cell Function, Annual Review of Immunology, vol.22, issue.1, pp.817-890, 2004. ,
DOI : 10.1146/annurev.immunol.22.012703.104608
CD1 antigen presentation: how it works, Nature Reviews Immunology, vol.200, issue.12, pp.929-941, 2007. ,
DOI : 10.1038/nri2191
Nonglycosidic agonists of invariant NKT cells for use as vaccine adjuvants ChemMedChem, pp.171-175, 2009. ,
Costimulation-dependent modulation of experimental autoimmune encephalomyelitis by ligand stimulation of V?14 NKT cells, Journal of Immunology, issue.166, pp.662-668, 2001. ,
Antigen presentation by chemically modified splenocytes induces antigen- specific T cell unresponsiveness in vitro and in vivo, Journal of Experimental Medicine, vol.165, issue.2, pp.302-319, 1987. ,
DOI : 10.1084/jem.165.2.302
Transcriptional Mechanisms Underlying Lymphocyte Tolerance, Cell, vol.109, issue.6, pp.719-732, 2002. ,
DOI : 10.1016/S0092-8674(02)00767-5
Molecular regulation of T-cell anergy, EMBO reports, vol.2000, issue.1, pp.50-55, 2008. ,
DOI : 10.1038/ni1394
A Role for Mammalian Target of Rapamycin in Regulating T Cell Activation versus Anergy, The Journal of Immunology, vol.178, issue.4, pp.2163-2170, 2007. ,
DOI : 10.4049/jimmunol.178.4.2163
Induction of T cell anergy: integration of environmental cues and infectious tolerance, Current Opinion in Immunology, vol.22, issue.5, pp.552-559, 2010. ,
DOI : 10.1016/j.coi.2010.08.005
Immunoregulatory functions of mTOR inhibition, Nature Reviews Immunology, vol.147, issue.5, pp.324-337, 2009. ,
DOI : 10.1038/nri2546
Prolonged IFN-?????producing NKT response induced with ??-galactosylceramide???loaded DCs, Nature Immunology, vol.3, issue.9, pp.867-874, 2002. ,
DOI : 10.1038/ni827
Glycolipid antigen induces long-term natural killer T cell anergy in mice, Journal of Clinical Investigation, vol.115, issue.9, pp.2572-2583, 2005. ,
DOI : 10.1172/JCI24762DS1
Nanoparticle formulated alpha-galactosylceramide activates NKT cells without inducing anergy, Vaccine, vol.27, issue.25-26, pp.3484-3488, 2009. ,
DOI : 10.1016/j.vaccine.2009.01.047
Antitumor Activities of Alpha-Monogalactosylceramides ,
Bioorganic and Medicinal Chemistry Letters, pp.705-710, 1995. ,
Murine CD1d-Restricted T Cell Recognition of Cellular Lipids, Immunity, vol.12, issue.2, pp.211-221, 2000. ,
DOI : 10.1016/S1074-7613(00)80174-0
Recognition of Lyso-Phospholipids by Human Natural Killer T Lymphocytes, PLoS Biology, vol.170, issue.10, p.1000228, 2009. ,
DOI : 10.1371/journal.pbio.1000228.s001
Enzymatic synthesis of Gb3 and iGb3 ceramides, Carbohydrate Research, vol.345, issue.10, pp.1384-1388, 2010. ,
DOI : 10.1016/j.carres.2010.02.006
Lysosomal Glycosphingolipid Recognition by NKT Cells, Lysosomal Glycosphingolipid Recognition by NKT cell, pp.1786-1789, 2004. ,
DOI : 10.1126/science.1103440
Defective presentation of CD1d 1-restricted natural V?14J?18 NKT lymphocyte antigen caused by ??Dglucosylceramide synthase deficiency, Proceedings of the National Academy of Sciences of the United States of America, pp.1849-1854, 2003. ,
Sensitive detection of isoglobo and globo series tetraglycosylceramides in human thymus by ion trap mass spectrometry, Glycobiology, vol.18, issue.2, pp.158-165, 2008. ,
DOI : 10.1093/glycob/cwm129
Prevention of Autoimmunity by Targeting a Distinct, Noninvariant CD1d-reactive T Cell Population Reactive to Sulfatide, The Journal of Experimental Medicine, vol.160, issue.7, pp.947-957, 0199. ,
DOI : 10.1038/35097097
Mycobacterial phosphatidylinositol mannoside is a natural antigen for CD1d-restricted T cells, Proceedings of the National Academy of Sciences of the United States of America, pp.10685-10690, 2004. ,
DOI : 10.1073/pnas.0403787101
Lipid and glycolipid antigens of CD1d-restricted natural killer T cells, Seminars in Immunology, vol.22, issue.2, pp.68-78, 2009. ,
DOI : 10.1016/j.smim.2009.10.003
Natural killer T cells activated by a lipopeptidophosphoglycan from Entamoeba histolytica are critically important to control amebic liver abscess The crystal structure of human CD1d with and without alpha-galactosylceramide, PloS Pathogens Nature Immunology, issue.6, pp.819-826, 2005. ,
Design of natural killer T cell activators: Structure and function of a microbial glycosphingolipid bound to mouse CD1d, Proceedings of the National Academy Sciences of United States of America, pp.3972-3977, 2006. ,
DOI : 10.1073/pnas.0600285103
Structure???activity relationship and conformational analysis of monoglycosylceramides on the syngeneic mixed leukocyte reaction, Bioorganic & Medicinal Chemistry, vol.6, issue.10, pp.1905-1910, 1998. ,
DOI : 10.1016/S0968-0896(98)00112-6
Indian task force for celiac disease: Current status, World Journal of Gastroenterology, vol.15, issue.48, pp.6028-6061, 2009. ,
DOI : 10.3748/wjg.15.6028
Synthesis and biological activity of ??-l-fucosyl ceramides, analogues of the potent agonist, ??-d-galactosyl ceramide KRN7000, Bioorganic & Medicinal Chemistry Letters, vol.20, issue.11, pp.3223-3226, 2010. ,
DOI : 10.1016/j.bmcl.2010.04.079
Immunomodulatory ??-Galactoglycosphingolipids: Synthesis of 2'-Fluoro-2'-deoxy-??-galactosylceramide and an Evaluation of Its Immunostimulating Properties, European Journal of Organic Chemistry, vol.65, issue.15 ,
DOI : 10.1002/ejoc.200500053
Synthesis and biological activity of ??-galactosyl ceramide KRN7000 and galactosyl (??1???2) galactosyl ceramide, Bioorganic & Medicinal Chemistry Letters, vol.19, issue.15, pp.4288-4291, 2009. ,
DOI : 10.1016/j.bmcl.2009.05.095
Synthesis and evaluation of 3???- and 4???-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000, Bioorganic & Medicinal Chemistry Letters, vol.19, issue.15, pp.4122-4125, 2009. ,
DOI : 10.1016/j.bmcl.2009.06.005
The Roles of 3??? and 4??? Hydroxy Groups in ??-Galactosylceramide Stimulation of Invariant Natural Killer T???Cells, ChemMedChem, vol.434, issue.11, pp.1810-1815, 2009. ,
DOI : 10.1002/cmdc.200900350
Synthesis and human NKT cell stimulating properties of 3-O-sulfo-a/b- galactosylceramides. Bioorganic and Medicinal Chemistry Letters, pp.2907-2916, 2005. ,
Introduction of aromatic group on 4???-OH of ??-GalCer manipulated NKT cell cytokine production, Bioorganic & Medicinal Chemistry, vol.19, issue.8, pp.2767-2776, 2010. ,
DOI : 10.1016/j.bmc.2010.11.061
A Pegylated Derivative of ??-Galactosylceramide Exhibits Improved Biological Properties, The Journal of Immunology, vol.179, issue.4, pp.2065-2073, 2007. ,
DOI : 10.4049/jimmunol.179.4.2065
Synthesis and NKT Cell Stimulating Properties of Fluorophore- and Biotin-Appended 6?????????-Amino-6?????????-deoxy-galactosylceramides, Organic Letters, vol.4, issue.8, pp.1267-1270, 2002. ,
DOI : 10.1021/ol025565+
RCAI-61, the 6???-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-?? in vivo, Tetrahedron Letters, vol.49, issue.48, pp.6827-6830, 2008. ,
DOI : 10.1016/j.tetlet.2008.09.074
6???-Derivatised ??-GalCer Analogues Capable of Inducing Strong CD1d-Mediated Th1-Biased NKT Cell Responses in Mice, Journal of the American Chemical Society, vol.130, issue.49, pp.16468-16469, 2008. ,
DOI : 10.1021/ja8064182
Galactose-modified iNKT cell agonists stabilized by an induced fit of CD1d prevent tumour metastasis, The EMBO Journal, vol.202, issue.11, pp.2294-2305, 2011. ,
DOI : 10.1038/emboj.2011.145
RCAI-56, a carboxylic analogue of KRN7000 : its synthesis and potent activity for natural (NK) T cells to preferentially produce interferon-?, Tetrahedron Letters, issue.48, pp.3343-3347, 2007. ,
RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines???, Bioorganic & Medicinal Chemistry, vol.17, issue.17, pp.6360-6373, 2009. ,
DOI : 10.1016/j.bmc.2009.07.025
??-galactosylceramide alters invariant natural killer T cell function and is effective treatment for lupus, Clinical Immunology, vol.132, issue.3, pp.321-333, 2009. ,
DOI : 10.1016/j.clim.2009.05.018
Superior Protection against Malaria and Melanoma Metastases by a C-glycoside Analogue of the Natural Killer T Cell Ligand ??-Galactosylceramide, The Journal of Experimental Medicine, vol.8, issue.11, pp.1631-1641, 0198. ,
DOI : 10.1046/j.1423-0410.2002.00217.x
The C-glycoside analogue of the immunostimulant ?-galactosylceramide (KRN7000) : synthesis and striking enhancement of activity, Angewandte Chemie International Edition, issue.43, pp.3818-3822, 2004. ,
-Galactosylceramides:?? Synthesis and Immunology, Accounts of Chemical Research, vol.39, issue.10, pp.692-701, 2006. ,
DOI : 10.1021/ar050006z
URL : https://hal.archives-ouvertes.fr/hal-00607361
Invariant TCR Rather Than CD1d Shapes the Preferential Activities of C-Glycoside Analogues Against Human Versus Murine Invariant NKT Cells, The Journal of Immunology, vol.183, issue.7, pp.4415-4421, 2009. ,
DOI : 10.4049/jimmunol.0901021
Synthesis and evaluation of an ?-Cgalactosylceramide analogue that induces Th1-biased responses in human natural killer T cells, ChemBioChem, issue.7, pp.1750-1756, 2006. ,
The First Synthesis of a Thioglycoside Analogue of the Immunostimulant KRN7000, Organic Letters, vol.10, issue.20, pp.4641-4644, 2008. ,
DOI : 10.1021/ol8019555
Potent immune-modulating and anticancer effects of NKT cell stimulatory glycolipids, Proceedings of the National Academy of Sciences, pp.10299-10304, 2007. ,
DOI : 10.1073/pnas.0703824104
Activation of human invariant natural killer T cells with a thioglycoside analogue of ?galactosylceramide, Clinical Immunology, 2011. ,
Galacto-Configured Aminocyclitol Phytoceramides Are Potent in Vivo Invariant Natural Killer T Cell Stimulators, Journal of the American Chemical Society, vol.133, issue.31, pp.12079-12084, 2011. ,
DOI : 10.1021/ja202610x
Synthesis and Evaluation of 1,2,3-Triazole Containing Analogues of the Immunostimulant ??-GalCer, Journal of Medicinal Chemistry, vol.50, issue.3, pp.585-589, 2007. ,
DOI : 10.1021/jm061243q
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, Bioorganic and Medicinal Chemistry, pp.950-964, 2008. ,
DOI : 10.1016/j.bmc.2007.10.008
Synthesis and biological activity of ester and ether analogues of ?-galactosylceramide (KRN7000) Carbohydrate Research, pp.1663-1684, 2010. ,
Synthesis and Evaluation of Amino-Modified ??-GalCer Analogues, Organic Letters, vol.12, issue.13, pp.2928-2931, 2010. ,
DOI : 10.1021/ol100934z
Effects of Lipid Chain Lengths in ??-Galactosylceramides on Cytokine Release by Natural Killer T Cells, Journal of the American Chemical Society, vol.126, issue.42, pp.13602-13603, 2004. ,
DOI : 10.1021/ja045385q
Modulation of CD1d-restricted NKT cell reponses by using N-acyl variants of ?- Galactosylceramides, Proceedings of the National Academy of Sciences, pp.3383-3388, 2005. ,
Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH, Bioorganic & Medicinal Chemistry Letters, vol.19, issue.13, pp.3386-3388, 2009. ,
DOI : 10.1016/j.bmcl.2009.05.042
Structure-Based Discovery of Glycolipids for CD1d-Mediated NKT Cell Activation:?? Tuning the Adjuvant versus Immunosuppression Activity, Journal of the American Chemical Society, vol.128, issue.28, pp.9022-9023, 2006. ,
DOI : 10.1021/ja062740z
Potent immuno-modulating and anticancer effects of NKT cell stimulatory glycolipids, Proceedings of the National Academy of Sciences, pp.10299-10304, 2007. ,
Quantitative Microarray Analysis of Intact Glycolipid???CD1d Interaction and Correlation with Cell-Based Cytokine Production, Journal of the American Chemical Society, vol.130, issue.37, pp.12348-12354, 2008. ,
DOI : 10.1021/ja8012787
An ??-GalCer analogue with branched acyl chain enhances protective immune responses in a nasal influenza vaccine, Vaccine, vol.29, issue.3, pp.417-425, 2010. ,
DOI : 10.1016/j.vaccine.2010.11.005
Synthesis and Evaluation of Sphinganine Analogues of KRN7000 and OCH, The Journal of Organic Chemistry, vol.70, issue.25, pp.10260-10270, 2005. ,
DOI : 10.1021/jo051147h
A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells, Nature, vol.5, issue.6855, pp.531-534, 2001. ,
DOI : 10.1038/35097097
Synthesis of ??-Galactosyl Ceramide (KRN7000) and Analogues Thereof via a Common Precursor and Their Preliminary Biological Assessment, The Journal of Organic Chemistry, vol.73, issue.22, pp.9192-9195, 2008. ,
DOI : 10.1021/jo8019994
CD1d???lipid-antigen recognition by the semi-invariant NKT T-cell receptor, Nature, vol.18, issue.7149, pp.44-49, 2007. ,
DOI : 10.1038/nature05907
Reciprocal Control of T Helper Cell and Dendritic Cell Differentiation, Science, vol.283, issue.5405, pp.1183-1186, 1999. ,
DOI : 10.1126/science.283.5405.1183
Glycolipid presentation to natural killer T cells differs in an organ-dependant fashion, Proceedings of the National Academy Sciences of United States of America, pp.1127-1132, 2005. ,
Particulate Systems as Adjuvants and Carriers for Peptide and Protein Antigens, Current Drug Delivery, vol.3, issue.4, pp.379-388, 2006. ,
DOI : 10.2174/156720106778559029
A Review on Composite Liposomal Technologies for Specialized Drug Delivery, Journal of Drug Delivery, vol.30, issue.16, p.939851, 2009. ,
DOI : 10.1023/A:1006137100444
Role of nanotechnology in targeted drug delivery and imaging: a concise review, Nanomedicine: Nanotechnology, Biology and Medicine, vol.1, issue.3, pp.193-212, 2005. ,
DOI : 10.1016/j.nano.2005.06.004
Solid lipid nanoparticles (SLN) for controlled drug delivery ?????? a review of the state of the art, European Journal of Pharmaceutics and Biopharmaceutics, vol.50, issue.1, pp.161-177, 2000. ,
DOI : 10.1016/S0939-6411(00)00087-4
The influence of lipid nanocapsule composition on their size distribution, European Journal of Pharmaceutical Sciences, vol.18, issue.1, pp.55-61, 2003. ,
DOI : 10.1016/S0928-0987(02)00241-5
The preparation and properties of niosomes-non-ionic surfactant vesicles, Journal of Pharmacy and Pharmacology, vol.9, issue.Suppl. 36, pp.863-868, 1985. ,
DOI : 10.1111/j.2042-7158.1985.tb04990.x
Polycyanoacrylate nanocapsules as potential lysosomotropic carriers: preparation, morphological and sorptive properties, Journal of Pharmacy and Pharmacology, vol.63, issue.1, pp.31-331, 1979. ,
DOI : 10.1111/j.2042-7158.1979.tb13510.x
Nanosized cationic hydrogels for drug delivery: preparation, properties and interactions with cells, Advanced Drug Delivery Reviews, vol.54, issue.1, pp.135-147, 2002. ,
DOI : 10.1016/S0169-409X(01)00245-9
Dendrimers in drug research, Chemical Society Reviews, vol.33, issue.1, pp.43-63, 2004. ,
DOI : 10.1039/b309043b
Synergistically Integrated Nanoparticles as Multimodal Probes for Nanobiotechnology, Accounts of Chemical Research, vol.41, issue.12, pp.1630-1640, 2008. ,
DOI : 10.1021/ar800045c
Synthesis, Stability, and Cellular Internalization of Gold Nanoparticles Containing Mixed Peptide???Poly(ethylene glycol) Monolayers, Analytical Chemistry, vol.79, issue.6, pp.2221-2229, 2007. ,
DOI : 10.1021/ac061578f
Growth model for carbon nanotubes, Physical Review Letters, vol.69, issue.21, pp.3100-3103, 1992. ,
DOI : 10.1103/PhysRevLett.69.3100
A Brief Summary of Carbon Nanotubes Science and Technology: A Health and Safety Perspective, ChemSusChem, vol.68, issue.7 ,
DOI : 10.1002/cssc.201100161
Liposome: quo vadis ? Pharmaceutical Science & Technology Today, pp.19-31, 1998. ,
Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors., Proceedings of the National Academy of Sciences of the United States of America, pp.6949-6953, 1988. ,
DOI : 10.1073/pnas.85.18.6949
Stealth liposomes avoiding reticuloendothelial uptake in Liposome in the Therapy of Infectious Diseases and Cancer, pp.405-415, 1989. ,
Liposome : A review, Journal of Pharmacy Research, issue.7, pp.1163-1167, 2009. ,
Mechanism of NKT cell activation by intranasal coadministration of alpha-galactosylceramide, which can induce cross-protection against influenza viruses, Mucosal Immunology, issue.1, pp.208-218, 2008. ,
Synthesis of truncated analogues of the iNKT cell agonist, ??-galactosyl ceramide (KRN7000), and their biological evaluation, Bioorganic & Medicinal Chemistry, vol.19, issue.1, pp.221-228, 2011. ,
DOI : 10.1016/j.bmc.2010.11.032
An improved synthesis of dansylated ??-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells, Carbohydrate Research, vol.346, issue.7, pp.914-926, 2011. ,
DOI : 10.1016/j.carres.2011.02.014
Synthesis of D-erythrodihydrosphingosine and D-xylo-phytosphingosine from a serine-derived 1,5- dioxaspiro[3.2]hexane template, Organic Letters, issue.4, pp.1719-1722, 2002. ,
The synthesis and configurational stability of differentially protected .beta.-hydroxy-.alpha.-amino aldehydes, The Journal of Organic Chemistry, vol.52, issue.12, pp.2361-2364, 1987. ,
DOI : 10.1021/jo00388a004
-Serine, The Journal of Organic Chemistry, vol.65, issue.11, pp.3538-3541, 2000. ,
DOI : 10.1021/jo991447x
URL : https://hal.archives-ouvertes.fr/hal-00309399
NKT Cells in the Production of Antilipid Antibodies, Bioconjugate Chemistry, vol.21, issue.4, pp.741-747, 2010. ,
DOI : 10.1021/bc9005255
A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate, Carbohydrate Research, vol.343, issue.10-11, pp.1858-1862, 2008. ,
DOI : 10.1016/j.carres.2008.03.002
Total synthesis of ??-galactosyl cerebroside, Carbohydrate Research, vol.328, issue.2, pp.95-102, 2000. ,
DOI : 10.1016/S0008-6215(00)00092-6
Synthesis of ??-Galactosyl Ceramide, a Potent Immunostimulatory Agent, The Journal of Organic Chemistry, vol.67, issue.13, pp.4559-4564, 2002. ,
DOI : 10.1021/jo0201530
Practical synthesis of oligosaccharides. Partial synthesis of avermectin Bla, Journal of American Chemical Society, issue.106, pp.4189-4192, 1984. ,
Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice, Journal of Medicinal Chemistry, vol.38, issue.12, pp.2176-2187, 1995. ,
DOI : 10.1021/jm00012a018
Glycosyl iodides are highly efficient donors under neutral conditions, Carbohydrate Research, vol.320, issue.1-2, pp.61-69, 1999. ,
DOI : 10.1016/S0008-6215(99)00146-9
Halide ion catalyzed glycosidation reactions. Syntheses of .alpha.-linked disaccharides, Journal of the American Chemical Society, vol.97, issue.14, pp.4056-4062, 1975. ,
DOI : 10.1021/ja00847a032
Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs. Bioorganic and Medicinal Chemistry Letters, pp.2781-2784, 2007. ,
Synthesis of NBD-alpha-galactosylceramide and its immunologic properties, Organic Letters, issue.1, pp.359-361, 1999. ,
Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY ?galactosylceramide, ChemBioChem, issue.4, pp.27-33, 2003. ,
(WO2008047174A1) Alpha-Galactosylceramide analogs, their methods of manufacture, intermediate compounds useful in these methods, and pharmaceutical compositions containing them, pp.1-113, 2008. ,
ATCC BAA-400, The Journal of Organic Chemistry, vol.72, issue.14, pp.5427-5430, 2007. ,
DOI : 10.1021/jo070629l
Synthesis of three regioisomers of the pentasaccharide part of the Skp1 glycoprotein of Dictyostelium discoideum, Tetrahedron: Asymmetry, vol.20, issue.6-8, pp.808-820, 2009. ,
DOI : 10.1016/j.tetasy.2009.02.040
A Concise synthesis of (2S,3S,4S)-2- (Hydroxymethyl)pyrrolidine-3,4-diol (LAB1). Synthesis, pp.3063-3066, 2010. ,
The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement, The Journal of Organic Chemistry, vol.57, issue.10, pp.2768-2771, 1992. ,
DOI : 10.1021/jo00036a003
Synthesis and solvolysis of some D-glucopyranosyl bromides having a benzyl group at C-2, The Journal of Organic Chemistry, vol.34, issue.3, pp.563-571, 1969. ,
DOI : 10.1021/jo01255a018
Activation of Invariant NKT Cells by Toll-like Receptor 9-Stimulated Dendritic Cells Requires Type I Interferon and Charged Glycosphingolipids, Immunity, vol.27, issue.4, pp.597-609, 2007. ,
DOI : 10.1016/j.immuni.2007.08.017
URL : https://hal.archives-ouvertes.fr/hal-00317178
Spleen-Resident CD4 and CD4 CD8alpha Dendritic Cell Subsets Differ in Their Ability to Prime Invariant Natural Killer T Lymphocytes, PLoS One, issue.6, p.26919, 2011. ,
Preparation of liposomes of defined size distribution by extrusion through polycarbonate membranes, Biochimica et Biophysica Acta (BBA) - Biomembranes, vol.557, issue.1 ,
DOI : 10.1016/0005-2736(79)90085-3
Procedure for preparation of liposomes with large internal aqueous space and high capture by reverse-phase evaporation., Proceedings of the National Academy of Sciences of the United States of America, pp.75-4194, 1978. ,
DOI : 10.1073/pnas.75.9.4194
Consistent and fast inhibition of colon carcinogenesis by polyethylene glycol in mice and rats given various carcinogens, Cancer Research, vol.60, pp.3160-3164, 2000. ,
Surface modified superparamagnetic nanoparticles for drug delivery: Interaction studies with human fibroblasts in culture, Journal of Materials Science: Materials in Medicine, vol.15, issue.4, pp.493-496, 2004. ,
DOI : 10.1023/B:JMSM.0000021126.32934.20
Insertion of poly(ethylene glycol) derivatized phospholipid into pre-formed liposomes results in prolonged in vivo circulation time, FEBS Letters, vol.2, issue.2-3, pp.243-246, 1996. ,
DOI : 10.1016/0014-5793(96)00452-8
Sterically stabilized liposomes: improvements in pharmacokinetics and antitumor therapeutic efficacy., Proceedings of the National Academy of Sciences of the United States of America, pp.11460-11464, 1991. ,
DOI : 10.1073/pnas.88.24.11460
Influence of poly(ethylene glycol) grafting density and polymer length on liposomes: Relating plasma circulation lifetimes to protein binding, Biochimica et Biophysica Acta (BBA) - Biomembranes, vol.1768, issue.6, pp.1367-1377, 1768. ,
DOI : 10.1016/j.bbamem.2006.12.013
Influence of Ligand Valency on the Targeting of Immature Human Dendritic Cells by Mannosylated Liposomes, Bioconjugate Chemistry, vol.19, issue.12, pp.2385-2393, 2008. ,
DOI : 10.1021/bc8002524
The mannose receptor: linking homeostasis and immunity through sugar recognition, Trends in Immunology, vol.26, issue.2, pp.104-110, 2005. ,
DOI : 10.1016/j.it.2004.12.001
Collagen binding by the mannose receptor mediated through the fibronectin type II domain, Biochemical Journal, vol.395, issue.3, pp.579-586, 2006. ,
DOI : 10.1042/BJ20052027
Dendritic cells use macropinocytosis and the mannose receptor to concentrate macromolecules in the major histocompatibility complex class II compartment: downregulation by cytokines and bacterial products, Journal of Experimental Medicine, vol.182, issue.2, pp.389-400, 1995. ,
DOI : 10.1084/jem.182.2.389
The mannose receptor functions as a high capacity and broad specificity antigen receptor in human dendritic cells, European Journal of Immunology, vol.144, issue.9, pp.2417-2425, 1997. ,
DOI : 10.1002/eji.1830270941
CD11c/CD18, a transmembrane signaling receptor for lipopolysaccharide, Journal of Experimental Medicine, vol.181, issue.4, pp.1473-1479, 1995. ,
DOI : 10.1084/jem.181.4.1473
CD11c provides an effective immunotarget for the generation of both CD4 and CD8 T cell responses, European Journal of Immunology, vol.139, issue.8, pp.2263-2273, 2008. ,
DOI : 10.1002/eji.200838302
Red cell ICAM-4 is a ligand for the monocyte/macrophage integrin CD11c, CD18: characterization of the binding sites on ICAM-4. Blood, pp.802-810, 2007. ,
Targeting Dendritic Cells with Antigen-Containing Liposomes: A Highly Effective Procedure for Induction of Antitumor Immunity and for Tumor Immunotherapy, Cancer Research, vol.64, issue.12, pp.4357-4365, 2004. ,
DOI : 10.1158/0008-5472.CAN-04-0138
Approaching the Asymptote? Evolution and Revolution in Immunology, Cold Spring Harbor Symposia on Quantitative Biology, vol.54, issue.0, pp.1-13, 1989. ,
DOI : 10.1101/SQB.1989.054.01.003
Intracellular Toll-like Receptors, Immunity, vol.32, issue.3, pp.305-315, 2010. ,
DOI : 10.1016/j.immuni.2010.03.012
Pathogen Recognition and Innate Immunity, Cell, vol.124, issue.4, pp.783-801, 2006. ,
DOI : 10.1016/j.cell.2006.02.015
Synthesis of Thiol-Reactive Lipopeptide Adjuvants. Incorporation into Liposomes and Study of Their Mitogenic Effect on Mouse Splenocytes, Bioconjugate Chemistry, vol.15, issue.3, pp.541-553, 2004. ,
DOI : 10.1021/bc034184t
T cell receptor antagonist peptides induce positive selection, Cell, vol.76, issue.1, pp.17-27, 1994. ,
DOI : 10.1016/0092-8674(94)90169-4
Influence of poly(ethylene glycol) grafting density and polymer length on liposomes: Relating plasma circulation lifetimes to protein binding, Biochimica et Biophysica Acta (BBA) - Biomembranes, vol.1768, issue.6, pp.1367-1377, 1768. ,
DOI : 10.1016/j.bbamem.2006.12.013
The Biology of NKT Cells, Annual Review of Immunology, vol.25, issue.1, pp.297-336, 2007. ,
DOI : 10.1146/annurev.immunol.25.022106.141711
Antitumor activity of liposomal ErbB2/HER2 epitope peptide-based vaccine constructs incorporating TLR agonists and mannose receptor targeting, Biomaterials, vol.32, issue.20, pp.4574-4783, 2011. ,
DOI : 10.1016/j.biomaterials.2011.03.015
URL : https://hal.archives-ouvertes.fr/hal-00596925
Targeting lymph nodes with liposomes bearing anti-HLA-DR Fab??? fragments, Biochimica et Biophysica Acta (BBA) - Biomembranes, vol.1421, issue.2, pp.284-294, 1421. ,
DOI : 10.1016/S0005-2736(99)00137-6
URL : http://doi.org/10.1016/s0005-2736(99)00137-6
Targeting Dendritic Cells with Antigen-Containing Liposomes: A Highly Effective Procedure for Induction of Antitumor Immunity and for Tumor Immunotherapy, Cancer Research, vol.64, issue.12, pp.4357-4365, 2004. ,
DOI : 10.1158/0008-5472.CAN-04-0138
A Novel Toll-Like Receptor that Recognizes Bacterial DNA, Nature, vol.408, pp.740-745, 2000. ,
DOI : 10.1385/1-59259-305-4:039
Design of a Liposomal Candidate Vaccine Against Pseudomonas aeruginosa and its Evaluation in Triggering Systemic and Lung Mucosal Immunity, Pharmaceutical Research, vol.26, issue.2, pp.276-285, 2009. ,
DOI : 10.1007/s11095-008-9724-y
Presentation of proteins encapsulated in sterically stabilized liposomes by dendritic cells initiates CD8(+) T-cell responses in vivo, Blood, issue.96, pp.3505-3513, 2000. ,
Liposome-Coupled Peptides Induce Long-Lived Memory CD8+ T Cells Without CD4+ T Cells, PLoS ONE, vol.12, issue.2, p.15091, 2010. ,
DOI : 10.1371/journal.pone.0015091.g005
Activation of invariant Natural Killer T lymphocytes in response to the alpha-galactosylceramide analogue KRN7000 encapsulated in PLGA-based nanoparticles and microparticles, International Journal of Pharmaceutics, issue.423, pp.45-54, 2011. ,
Sustained activation and tumor targeting of NKT cells using a CD1d???anti-HER2???scFv fusion protein induce antitumor effects in mice, Journal of Clinical Investigation, vol.118, pp.994-1005, 2008. ,
DOI : 10.1172/JCI33249
Invariant NKT cell anergy is induced by a strong TCR-mediated signal plus co-stimulation, International Immunology, vol.22, issue.11, pp.905-913, 2010. ,
DOI : 10.1093/intimm/dxq444
PD-1/PD-L Blockade Prevents Anergy Induction and Enhances the Anti-Tumor Activities of Glycolipid-Activated Invariant NKT Cells, The Journal of Immunology, vol.182, issue.5, pp.2816-2826, 2009. ,
DOI : 10.4049/jimmunol.0803648
Two dimensional thin layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots, Lipids, vol.1, issue.5, pp.494-496, 1970. ,
DOI : 10.1007/BF02531316
A new enzymatic method for determination of serum choline-containing phospholipids, Clinica Chimica Acta, vol.79, pp.93-98, 1977. ,
Fluorometric assay of proteins in the nanogram range, Archives of Biochemistry and Biophysics, vol.155, issue.1, pp.213-220, 1973. ,
DOI : 10.1016/S0003-9861(73)80023-2