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Volumn 24, Issue 4, 2013, Pages 586-594

Design, synthesis, and functional activity of labeled CD1d glycolipid agonists

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; CELL MEMBRANES; CHAINS; CYTOLOGY; FATTY ACIDS; HYDROGEN; MOLECULES; T-CELLS;

EID: 84876467824     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300556e     Document Type: Article
Times cited : (13)

References (56)
  • 1
    • 0025238707 scopus 로고
    • Molecules related to class-I major histocompatibility complex antigens
    • Stroynowski, I. (1990) Molecules related to class-I major histocompatibility complex antigens Annu. Rev. Immunol. 8, 501-530
    • (1990) Annu. Rev. Immunol. , vol.8 , pp. 501-530
    • Stroynowski, I.1
  • 4
    • 77649234578 scopus 로고    scopus 로고
    • How invariant natural killer T cells respond to infection by recognizing microbial or endogenous lipid antigens
    • Brigl, M. and Brenner, M. B. (2010) How invariant natural killer T cells respond to infection by recognizing microbial or endogenous lipid antigens Semin. Immunol. 22, 79-86
    • (2010) Semin. Immunol. , vol.22 , pp. 79-86
    • Brigl, M.1    Brenner, M.B.2
  • 5
    • 34249103661 scopus 로고    scopus 로고
    • The unique role of natural killer T cells in the response to microorganisms
    • Tupin, E., Kinjo, Y., and Kronenberg, M. (2007) The unique role of natural killer T cells in the response to microorganisms Nat. Rev. Microbiol. 5, 405-417
    • (2007) Nat. Rev. Microbiol. , vol.5 , pp. 405-417
    • Tupin, E.1    Kinjo, Y.2    Kronenberg, M.3
  • 6
    • 70350546309 scopus 로고    scopus 로고
    • The contrasting roles of NKT cells in tumor immunity
    • Berzofsky, J. A. and Terabe, M. (2009) The contrasting roles of NKT cells in tumor immunity Curr. Mol. Med. 9, 667-672
    • (2009) Curr. Mol. Med. , vol.9 , pp. 667-672
    • Berzofsky, J.A.1    Terabe, M.2
  • 7
    • 36048995442 scopus 로고    scopus 로고
    • NKT cells in immunoregulation of tumor immunity: A new immunoregulatory axis
    • Terabe, M. and Berzofsky, J. A. (2007) NKT cells in immunoregulation of tumor immunity: A new immunoregulatory axis Trends Immunol. 28, 491-496
    • (2007) Trends Immunol. , vol.28 , pp. 491-496
    • Terabe, M.1    Berzofsky, J.A.2
  • 8
    • 62749198174 scopus 로고    scopus 로고
    • Natural killer T cells and autoimmune diseases
    • Wu, L. and Van Kaer, L. (2009) Natural killer T cells and autoimmune diseases Curr. Mol. Med. 9, 4-14
    • (2009) Curr. Mol. Med. , vol.9 , pp. 4-14
    • Wu, L.1    Van Kaer, L.2
  • 9
    • 77950683098 scopus 로고    scopus 로고
    • An α-galactosylceramide C20:2 N -acyl variant enhances anti-inflammatory and regulatory T-cell independent responses that prevent type 1 diabetes
    • Ly, D., Tohn, R., Rubin, B., Blumenfeld, H., Besra, G. S., Veerapen, N., Porcelli, S. A., and Delovitch, T. L. (2010) An α-galactosylceramide C20:2 N -acyl variant enhances anti-inflammatory and regulatory T-cell independent responses that prevent type 1 diabetes Clin. Exp. Immunol. 160, 185-198
    • (2010) Clin. Exp. Immunol. , vol.160 , pp. 185-198
    • Ly, D.1    Tohn, R.2    Rubin, B.3    Blumenfeld, H.4    Besra, G.S.5    Veerapen, N.6    Porcelli, S.A.7    Delovitch, T.L.8
  • 10
    • 2342650811 scopus 로고    scopus 로고
    • Interleukin-4 but not interleukin-10 protects against spontaneous and recurrent type 1 diabetes by activated CD1d-restricted invariant natural killer T-cells
    • Mi, Q. A., Ly, D., Zucker, P., McGarry, M., and Delovitch, T. L. (2004) Interleukin-4 but not interleukin-10 protects against spontaneous and recurrent type 1 diabetes by activated CD1d-restricted invariant natural killer T-cells Diabetes 53, 1303-1310
    • (2004) Diabetes , vol.53 , pp. 1303-1310
    • Mi, Q.A.1    Ly, D.2    Zucker, P.3    McGarry, M.4    Delovitch, T.L.5
  • 11
    • 23244447028 scopus 로고    scopus 로고
    • Expansion and hyperactivity of CD1d-restricted NKT cells during the progression of systemic lupus erythematosus in (New Zealand Black × New Zealand White) F1 mice
    • Forestier, C., Molano, A., Im, J. S., Dutronc, Y., Diamond, B., Davidson, A., Illarionov, P. A., Besra, G. S., and Porcelli, S. A. (2005) Expansion and hyperactivity of CD1d-restricted NKT cells during the progression of systemic lupus erythematosus in (New Zealand Black × New Zealand White) F1 mice J. Immunol. 175, 763-770
    • (2005) J. Immunol. , vol.175 , pp. 763-770
    • Forestier, C.1    Molano, A.2    Im, J.S.3    Dutronc, Y.4    Diamond, B.5    Davidson, A.6    Illarionov, P.A.7    Besra, G.S.8    Porcelli, S.A.9
  • 13
    • 0024586992 scopus 로고
    • Isolation and characterization of a cDNA and gene coding for a fourth CD1 molecule
    • Balk, S. P., Bleicher, P. A., and Terhorst, C. (1989) Isolation and characterization of a cDNA and gene coding for a fourth CD1 molecule Proc. Natl. Acad. Sci. U.S.A. 86, 252-256
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 252-256
    • Balk, S.P.1    Bleicher, P.A.2    Terhorst, C.3
  • 17
    • 28744453420 scopus 로고    scopus 로고
    • h2 polarization by OCH is supported by incompetent NKT cell induction of CD40L and following production inflammatory cytokines by bystander cells in vivo
    • h2 polarization by OCH is supported by incompetent NKT cell induction of CD40L and following production inflammatory cytokines by bystander cells in vivo Int. Immunol. 17, 1619-1629
    • (2005) Int. Immunol. , vol.17 , pp. 1619-1629
    • Oki, S.1    Tomi, C.2    Yamamura, T.3    Miyake, S.4
  • 18
    • 0345167831 scopus 로고    scopus 로고
    • Superior protection against malaria and melanoma metastases by a C -glycoside analogue of the natural killer T cell ligand α- galactosylceramide
    • Schmieg, J., Yang, G., Franck, R. W., and Tsuji, M. (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, 1631-1641
    • (2003) J. Exp. Med. , vol.198 , pp. 1631-1641
    • Schmieg, J.1    Yang, G.2    Franck, R.W.3    Tsuji, M.4
  • 19
    • 4444295929 scopus 로고    scopus 로고
    • The C-glycoside analogue of the immunostimulant α- galactosylceramide (KRN7000): Synthesis and striking enhancement of activity
    • Yang, G., Schmieg, J., Tsuji, M., and Franck, R. W. (2004) The C-glycoside analogue of the immunostimulant α-galactosylceramide (KRN7000): Synthesis and striking enhancement of activity Angew. Chem., Int. Ed. 43, 3818-3822
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3818-3822
    • Yang, G.1    Schmieg, J.2    Tsuji, M.3    Franck, R.W.4
  • 20
    • 55249084382 scopus 로고    scopus 로고
    • Synthetic glycolipid ligands for human iNKT cells as potential therapeutic agents for immunotherapy
    • Araki, M., Miyake, S., and Yamamura, T. (2008) Synthetic glycolipid ligands for human iNKT cells as potential therapeutic agents for immunotherapy Curr. Med. Chem. 15, 2337-2345
    • (2008) Curr. Med. Chem. , vol.15 , pp. 2337-2345
    • Araki, M.1    Miyake, S.2    Yamamura, T.3
  • 21
    • 68149168633 scopus 로고    scopus 로고
    • Incorporation of NKT cell-activating glycolipids enhances immunogenicity and vaccine efficacy of Mycobacterium bovis bacillus Calmette-Guerin
    • Venkataswamy, M. M., Baena, A., Goldberg, M. F., Bricard, G., Im, J. S., Chan, J., Reddington, F., Besra, G. S., Jacobs, W. R., and Porcelli, S. A. (2009) Incorporation of NKT cell-activating glycolipids enhances immunogenicity and vaccine efficacy of Mycobacterium bovis bacillus Calmette-Guerin J. Immunol. 183, 1644-1656
    • (2009) J. Immunol. , vol.183 , pp. 1644-1656
    • Venkataswamy, M.M.1    Baena, A.2    Goldberg, M.F.3    Bricard, G.4    Im, J.S.5    Chan, J.6    Reddington, F.7    Besra, G.S.8    Jacobs, W.R.9    Porcelli, S.A.10
  • 25
    • 65549083745 scopus 로고    scopus 로고
    • 14C]threitol ceramide, non-glycosidic analogues of the potent CD1d antigen α-galactosyl ceramide
    • 14C]threitol ceramide, non-glycosidic analogues of the potent CD1d antigen α-galactosyl ceramide Tetrahedron: Asymmetry 20, 747-753
    • (2009) Tetrahedron: Asymmetry , vol.20 , pp. 747-753
    • Garcia-Diaz, Y.R.1    Wojno, J.2    Cox, L.R.3    Besra, G.S.4
  • 28
    • 2942739333 scopus 로고    scopus 로고
    • The clinical implication and molecular mechanism of preferential IL-4 production by modified glycolipid-stimulated NKT cells
    • Oki, S., Chiba, A., Yamamura, Y., and Miyake, S. (2004) The clinical implication and molecular mechanism of preferential IL-4 production by modified glycolipid-stimulated NKT cells J. Clin. Invest. 113, 1631-1640
    • (2004) J. Clin. Invest. , vol.113 , pp. 1631-1640
    • Oki, S.1    Chiba, A.2    Yamamura, Y.3    Miyake, S.4
  • 30
    • 77649231838 scopus 로고    scopus 로고
    • Lipid and glycolipid antigens of CD1d-restricted natural killer T cells
    • Venkataswamy, M. M. and Porcelli, S. A. (2010) Lipid and glycolipid antigens of CD1d-restricted natural killer T cells Semin. Immunol. 22, 68-78
    • (2010) Semin. Immunol. , vol.22 , pp. 68-78
    • Venkataswamy, M.M.1    Porcelli, S.A.2
  • 35
    • 67649620059 scopus 로고    scopus 로고
    • Facile synthesis of biotin labelled α-galactosylceramide as antigen for invariant natural killer T cells
    • Xia, C., Zhang, W., Zhang, Y., Woodward, R. L., Wang, J., and Wang, P. G. (2009) Facile synthesis of biotin labelled α-galactosylceramide as antigen for invariant natural killer T cells Tetrahedron 65, 6390-6395
    • (2009) Tetrahedron , vol.65 , pp. 6390-6395
    • Xia, C.1    Zhang, W.2    Zhang, Y.3    Woodward, R.L.4    Wang, J.5    Wang, P.G.6
  • 36
    • 0037129390 scopus 로고    scopus 로고
    • Synthesis and NKT cell stimulating properties of fluorophore-and biotin-appended 6″-amino-6″-deoxy-galactosylceramides
    • Zhou, X.-T., Forestier, C., Goff, R. D., Li, C., Teyton, L., Bendelac, A., and Savage, P. B. (2002) Synthesis and NKT cell stimulating properties of fluorophore-and biotin-appended 6″-amino-6″-deoxy- galactosylceramides Org. Lett. 4, 1267-1270
    • (2002) Org. Lett. , vol.4 , pp. 1267-1270
    • Zhou, X.-T.1    Forestier, C.2    Goff, R.D.3    Li, C.4    Teyton, L.5    Bendelac, A.6    Savage, P.B.7
  • 38
    • 57549108830 scopus 로고    scopus 로고
    • 6′-Derivatised α-GalCer analogues capable of inducing strong CD1d-mediated Th1-biased NKT cell responses in mice
    • Trappeniers, M., Van Beneden, K., Decruy, T., Hillaert, U., Linclau, B., Elewaut, D., and Van Calenbergh, S. (2008) 6′-Derivatised α-GalCer analogues capable of inducing strong CD1d-mediated Th1-biased NKT cell responses in mice J. Am. Chem. Soc. 130, 16468-16469
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 16468-16469
    • Trappeniers, M.1    Van Beneden, K.2    Decruy, T.3    Hillaert, U.4    Linclau, B.5    Elewaut, D.6    Van Calenbergh, S.7
  • 39
    • 0033549676 scopus 로고    scopus 로고
    • Synthesis of NBD-α-galactosylceramide and its immunologic properties
    • Sakai, T., Ehara, H., and Koezuka, Y. (1999) Synthesis of NBD-α-galactosylceramide and its immunologic properties Org. Lett. 1, 359-361
    • (1999) Org. Lett. , vol.1 , pp. 359-361
    • Sakai, T.1    Ehara, H.2    Koezuka, Y.3
  • 40
    • 0033587102 scopus 로고    scopus 로고
    • Syntheses of biotinylated α-galactosylceramides and their effects on the immune system and CD1 molecules
    • Sakai, T., Naidenko, O. V., Iijima, H., Kronenberg, M., and Koezuka, Y. (1999) Syntheses of biotinylated α-galactosylceramides and their effects on the immune system and CD1 molecules J. Med. Chem. 42, 1836-1841
    • (1999) J. Med. Chem. , vol.42 , pp. 1836-1841
    • Sakai, T.1    Naidenko, O.V.2    Iijima, H.3    Kronenberg, M.4    Koezuka, Y.5
  • 41
    • 0037415043 scopus 로고    scopus 로고
    • Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY α-galactosylceramide
    • Vo-Hoang, Y., Micouin, L., Ronet, C., Gachelin, G., and Bonin, M. (2003) Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY α-galactosylceramide ChemBioChem 4, 27-33
    • (2003) ChemBioChem , vol.4 , pp. 27-33
    • Vo-Hoang, Y.1    Micouin, L.2    Ronet, C.3    Gachelin, G.4    Bonin, M.5
  • 43
    • 33846902068 scopus 로고    scopus 로고
    • Construction of Di-scFv through a trivalent alkyne-azide 1,3-dipolar cycloaddition
    • Poly(ethylene glycol) linkers are commonly used
    • Poly(ethylene glycol) linkers are commonly used. See, for example: Natarajan, A., Du, W., Xiong, C.-Y., DeNardo, G. L., DeNardo, S. J., and Gervay-Hague, J. (2007) Construction of Di-scFv through a trivalent alkyne-azide 1,3-dipolar cycloaddition Chem. Commun. 695-697
    • (2007) Chem. Commun. , pp. 695-697
    • Natarajan, A.1    Du, W.2    Xiong, C.-Y.3    Denardo, G.L.4    Denardo, S.J.5    Gervay-Hague, J.6
  • 44
    • 26944452043 scopus 로고    scopus 로고
    • PEGylation, successful approach to drug delivery
    • Veronese, F. M. and Pasut, G. (2005) PEGylation, successful approach to drug delivery Drug Discovery Today 10, 1451-1458
    • (2005) Drug Discovery Today , vol.10 , pp. 1451-1458
    • Veronese, F.M.1    Pasut, G.2
  • 46
    • 84985516415 scopus 로고
    • Enantioselective synthesis of (R)-amino acids using l -valine as a chiral agent
    • Schöllkopf, U., Groth, U., and Deng, C. (1981) Enantioselective synthesis of (R)-amino acids using l -valine as a chiral agent Angew. Chem., Int. Ed. 20, 798-799
    • (1981) Angew. Chem., Int. Ed. , vol.20 , pp. 798-799
    • Schöllkopf, U.1    Groth, U.2    Deng, C.3
  • 47
    • 84985580193 scopus 로고
    • Enantioselective synthesis of α-methyl-α-aminocarboxylic acids by alkylation of the lactim ether of cyclo -(l -Ala-l -Ala)
    • Schöllkopf, U., Hartwig, W., and Groth, U. (1979) Enantioselective synthesis of α-methyl-α-aminocarboxylic acids by alkylation of the lactim ether of cyclo -(l -Ala-l -Ala) Angew. Chem., Int. Ed. 18, 863-864
    • (1979) Angew. Chem., Int. Ed. , vol.18 , pp. 863-864
    • Schöllkopf, U.1    Hartwig, W.2    Groth, U.3
  • 50
    • 34848850746 scopus 로고    scopus 로고
    • An efficient, inexpensive and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride
    • Goddard-Borger, E. D. and Stick, R. V. (2007) An efficient, inexpensive and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride Org. Lett. 9, 3797-3800
    • (2007) Org. Lett. , vol.9 , pp. 3797-3800
    • Goddard-Borger, E.D.1    Stick, R.V.2
  • 51
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes
    • Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angew. Chem., Int. Ed. 41, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 52
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 40, 2004-2021
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 56
    • 78650867131 scopus 로고    scopus 로고
    • Synthesis of a versatile building block for the preparation of 6-N -derivatized α-galactosyl ceramides: Rapid access to biologically active glycolipids
    • Jervis, P. J., Cox, L. R., and Besra, G. S. (2011) Synthesis of a versatile building block for the preparation of 6-N -derivatized α-galactosyl ceramides: Rapid access to biologically active glycolipids J. Org. Chem. 76, 320-323
    • (2011) J. Org. Chem. , vol.76 , pp. 320-323
    • Jervis, P.J.1    Cox, L.R.2    Besra, G.S.3


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