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Volumn 6, Issue 4, 2015, Pages 476-480

Synthesis and biological activities of 5-thio-α-GALCERS

Author keywords

5 thio GalCer; antitumor activity; iNKT cells; KRN7000

Indexed keywords

1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; 5 THIO 1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; 5 THIO ALPHA GALACTOSYLCERAMIDE 566; ALPHA GALACTOSYLCERAMIDE; ANTINEOPLASTIC AGENT; CD1D ANTIGEN; GAMMA INTERFERON; IMMUNOSTIMULATING AGENT; INTERLEUKIN 4; UNCLASSIFIED DRUG;

EID: 84927621701     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.5b00046     Document Type: Article
Times cited : (17)

References (49)
  • 2
    • 38049065867 scopus 로고    scopus 로고
    • Application of natural killer T cells in antitumor immunotherapy
    • Hong, C.; Park, S.-H. Application of natural killer T cells in antitumor immunotherapy Crit. Rev. Immun. 2007, 27, 511-525
    • (2007) Crit. Rev. Immun. , vol.27 , pp. 511-525
    • Hong, C.1    Park, S.-H.2
  • 3
    • 41349091445 scopus 로고    scopus 로고
    • Clinical applications of natural killer T cell-based immunotherapy for cancer
    • Motohashi, S.; Nakayama, T. Clinical applications of natural killer T cell-based immunotherapy for cancer Cancer Sci. 2008, 99, 638-645
    • (2008) Cancer Sci. , vol.99 , pp. 638-645
    • Motohashi, S.1    Nakayama, T.2
  • 4
    • 70350546309 scopus 로고    scopus 로고
    • The contrasting roles of NKT cells in tumor immunity
    • Berzofsky, J. A.; Terabe, M. The contrasting roles of NKT cells in tumor immunity Curr. Mol. Med. 2009, 9, 667-672
    • (2009) Curr. Mol. Med. , vol.9 , pp. 667-672
    • Berzofsky, J.A.1    Terabe, M.2
  • 5
    • 34447637431 scopus 로고    scopus 로고
    • CD1-restricted T cells in host defense to infectious diseases
    • Behar, S. M.; Porcelli, S. A. CD1-restricted T cells in host defense to infectious diseases Curr. Top. Microbiol. Immun. 2007, 314, 215-250
    • (2007) Curr. Top. Microbiol. Immun. , vol.314 , pp. 215-250
    • Behar, S.M.1    Porcelli, S.A.2
  • 6
    • 34249103661 scopus 로고    scopus 로고
    • The unique role of natural killer T cells in the response to microorganisms
    • Tupin, E.; Kinjo, Y.; Kronenberg, M. The unique role of natural killer T cells in the response to microorganisms Nat. Rev. Microbiol. 2007, 5, 405-417
    • (2007) Nat. Rev. Microbiol. , vol.5 , pp. 405-417
    • Tupin, E.1    Kinjo, Y.2    Kronenberg, M.3
  • 7
    • 0028204397 scopus 로고
    • Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus
    • Natori, T.; Morita, M.; Akimoto, K.; Koezuka, Y. Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus Tetrahedron 1994, 50, 2771-2784
    • (1994) Tetrahedron , vol.50 , pp. 2771-2784
    • Natori, T.1    Morita, M.2    Akimoto, K.3    Koezuka, Y.4
  • 9
    • 0032729476 scopus 로고    scopus 로고
    • Cutting edge: Cross-talk between cells of the innate immune system: NKT cells rapidly activate NK cells
    • Carnaud, C.; Lee, D.; Donnars, O.; Park, S.-H.; Beavis, A.; Koezuka, Y.; Bendelac, A. Cutting edge: cross-talk between cells of the innate immune system: NKT cells rapidly activate NK cells J. Immunol. 1999, 163, 4647-4650
    • (1999) J. Immunol. , vol.163 , pp. 4647-4650
    • Carnaud, C.1    Lee, D.2    Donnars, O.3    Park, S.-H.4    Beavis, A.5    Koezuka, Y.6    Bendelac, A.7
  • 12
    • 0035807302 scopus 로고    scopus 로고
    • A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing Th2 bias of natural killer T cells
    • Miyamoto, K.; Miyake, S.; Yamamura, T. A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing Th2 bias of natural killer T cells Nature 2001, 413, 531-534
    • (2001) Nature , vol.413 , pp. 531-534
    • Miyamoto, K.1    Miyake, S.2    Yamamura, T.3
  • 15
    • 0041422186 scopus 로고    scopus 로고
    • α-galactosylceramide (KRN7000) suppression of chemical- and oncogene-dependent carcinogenesis
    • Hayakawa, Y.; Rovero, S.; Forni, G.; Smyth, M. J. α-galactosylceramide (KRN7000) suppression of chemical- and oncogene-dependent carcinogenesis Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9464-9469
    • (2003) Proc. Natl. Acad. Sci. U.S.A. , vol.100 , pp. 9464-9469
    • Hayakawa, Y.1    Rovero, S.2    Forni, G.3    Smyth, M.J.4
  • 17
    • 37349014075 scopus 로고    scopus 로고
    • Phase i study of α-galactosylceramide-pulsed antigen presenting cells administration to the nasal submucosa in unresectable or recurrent head and neck cancer
    • Uchida, T.; Horiguchi, S.; Tanaka, Y.; Yamamoto, H.; Kunii, N.; Motohashi, S.; Taniguchi, M.; Nakayama, T.; Okamoto, Y. Phase I study of α-galactosylceramide-pulsed antigen presenting cells administration to the nasal submucosa in unresectable or recurrent head and neck cancer Cancer Immunol. Immun. 2008, 57, 337-345
    • (2008) Cancer Immunol. Immun. , vol.57 , pp. 337-345
    • Uchida, T.1    Horiguchi, S.2    Tanaka, Y.3    Yamamoto, H.4    Kunii, N.5    Motohashi, S.6    Taniguchi, M.7    Nakayama, T.8    Okamoto, Y.9
  • 18
    • 23844523426 scopus 로고    scopus 로고
    • α-Galactosylceramide can act as a nasal vaccine adjuvant inducing protective immune responses against viral infection and tumor
    • Ko, S. Y.; Ko, H. J.; Chang, W. S.; Park, S. H.; Kweon, M. N.; Kang, C. Y. α-Galactosylceramide can act as a nasal vaccine adjuvant inducing protective immune responses against viral infection and tumor J. Immunol. 2005, 175, 3309-3317
    • (2005) J. Immunol. , vol.175 , pp. 3309-3317
    • Ko, S.Y.1    Ko, H.J.2    Chang, W.S.3    Park, S.H.4    Kweon, M.N.5    Kang, C.Y.6
  • 19
    • 11244304412 scopus 로고    scopus 로고
    • α-Galactosylceramide therapy for autoimmune diseases: Prospects and obstacles
    • Kaer, L. V. α-Galactosylceramide therapy for autoimmune diseases: prospects and obstacles Nat. Rev. Immunol. 2005, 5, 31-42
    • (2005) Nat. Rev. Immunol. , vol.5 , pp. 31-42
    • Kaer, L.V.1
  • 21
    • 0033022704 scopus 로고    scopus 로고
    • Immunization with α-galactosylceramide polarizes CD1-reactive NK T cells towards Th2 cytokine synthesis
    • Burdin, N.; Brossay, L.; Kronenberg, M. Immunization with α-galactosylceramide polarizes CD1-reactive NK T cells towards Th2 cytokine synthesis Eur. J. Immunol. 1999, 29, 2014-2025
    • (1999) Eur. J. Immunol. , vol.29 , pp. 2014-2025
    • Burdin, N.1    Brossay, L.2    Kronenberg, M.3
  • 22
    • 18044392378 scopus 로고    scopus 로고
    • Immunotherapeutic potential for ceramide-based activators of iNKT cells
    • Berkers, C. R.; Ovaa, H. Immunotherapeutic potential for ceramide-based activators of iNKT cells Trends Pharmacol. Sci. 2005, 26, 252-257
    • (2005) Trends Pharmacol. Sci. , vol.26 , pp. 252-257
    • Berkers, C.R.1    Ovaa, H.2
  • 24
    • 84862751941 scopus 로고    scopus 로고
    • Structure-activity relationship studies of novel glycosphingolipids that stimulate natural killer T-cells
    • Tashiro, T. Structure-activity relationship studies of novel glycosphingolipids that stimulate natural killer T-cells Biosci. Biotechnol. Biochem. 2012, 76, 1055-1067
    • (2012) Biosci. Biotechnol. Biochem. , vol.76 , pp. 1055-1067
    • Tashiro, T.1
  • 25
    • 79960422121 scopus 로고    scopus 로고
    • The 3-deoxy analogue of α-GalCer: Disclosing the role of the 4-hydroxyl group for CD1d-mediated NKT cell activation
    • Baek, D. J.; Seo, J. H.; Lim, C.; Kim, J. H.; Chung, D. H.; Cho, W. J.; Kang, C. Y.; Kim, S. The 3-deoxy analogue of α-GalCer: disclosing the role of the 4-hydroxyl group for CD1d-mediated NKT cell activation ACS Med. Chem. Lett. 2011, 2, 544-548
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 544-548
    • Baek, D.J.1    Seo, J.H.2    Lim, C.3    Kim, J.H.4    Chung, D.H.5    Cho, W.J.6    Kang, C.Y.7    Kim, S.8
  • 26
    • 84863136172 scopus 로고    scopus 로고
    • Heteroaromatic moieties in the sphingosine backbone of α-galactosylceramides for noncovalent interactions with CD1d
    • Kim, Y.; Kim, J.; Oh, K.; Lee, D. S.; Park, S. B. Heteroaromatic moieties in the sphingosine backbone of α-galactosylceramides for noncovalent interactions with CD1d ACS Med. Chem. Lett. 2012, 3, 151-154
    • (2012) ACS Med. Chem. Lett. , vol.3 , pp. 151-154
    • Kim, Y.1    Kim, J.2    Oh, K.3    Lee, D.S.4    Park, S.B.5
  • 27
    • 84898025489 scopus 로고    scopus 로고
    • Design and evaluation of ω-hydroxy fatty acids containing α-GalCer analogues for CD1d-mediated NKT cell activation
    • Lim, C.; Kim, J. H.; Baek, D. J.; Lee, J. Y.; Cho, M.; Lee, Y. S.; Kang, C. Y.; Chung, D. H.; Cho, W. J.; Kim, S. Design and evaluation of ω-hydroxy fatty acids containing α-GalCer analogues for CD1d-mediated NKT cell activation ACS Med. Chem. Lett. 2014, 5, 331-335
    • (2014) ACS Med. Chem. Lett. , vol.5 , pp. 331-335
    • Lim, C.1    Kim, J.H.2    Baek, D.J.3    Lee, J.Y.4    Cho, M.5    Lee, Y.S.6    Kang, C.Y.7    Chung, D.H.8    Cho, W.J.9    Kim, S.10
  • 29
    • 0032533447 scopus 로고    scopus 로고
    • Cutting edge: Structural requirements for galactosylceramide recognition by CD1-restricted NK T cells
    • Brossay, L.; Naidenko, O.; Burdin, N.; Matsuda, J.; Sakai, T.; Kronenberg, M. Cutting edge: structural requirements for galactosylceramide recognition by CD1-restricted NK T cells J. Immunol. 1998, 161, 5124-5128
    • (1998) J. Immunol. , vol.161 , pp. 5124-5128
    • Brossay, L.1    Naidenko, O.2    Burdin, N.3    Matsuda, J.4    Sakai, T.5    Kronenberg, M.6
  • 30
    • 6444240050 scopus 로고    scopus 로고
    • Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells
    • Goff, R. D.; Gao, Y.; Mattner, J.; Zhou, D.; Yin, N.; Cantu, C., III; Teyton, L.; Bendelac, A.; Savage, P. B. Effects of lipid chain lengths in α-galactosylceramides on cytokine release by natural killer T cells J. Am. Chem. Soc. 2004, 126, 13602-13603
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13602-13603
    • Goff, R.D.1    Gao, Y.2    Mattner, J.3    Zhou, D.4    Yin, N.5    Teyton, L.6    Bendelac, A.7    Savage, P.B.8
  • 31
    • 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.; Franck, R. W. The C-glycoside analogue of the immunostimulant α-galactosylceramide (KRN7000): synthesis and striking enhancement of activity Angew. Chem., Int. Ed. 2004, 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
  • 32
    • 33750608425 scopus 로고    scopus 로고
    • α-C-galactosylceramides: Synthesis and immunology
    • Franck, R. W.; Tsuji, M. α-C-galactosylceramides: synthesis and immunology Acc. Chem. Res. 2006, 39, 692-701
    • (2006) Acc. Chem. Res. , vol.39 , pp. 692-701
    • Franck, R.W.1    Tsuji, M.2
  • 34
    • 56249134249 scopus 로고    scopus 로고
    • The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000
    • Dere, R. T.; Zhu, X. The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000 Org. Lett. 2008, 10, 4641-4644
    • (2008) Org. Lett. , vol.10 , pp. 4641-4644
    • Dere, R.T.1    Zhu, X.2
  • 37
    • 79952438320 scopus 로고    scopus 로고
    • Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors
    • Xie, W.; Tanabe, G.; Akaki, J.; Morikawa, T.; Ninomiya, K.; Minematsu, T.; Yoshikawa, M.; Wu, X.; Muraoka, O. Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors Bioorg. Med. Chem. 2011, 19, 2015-2022
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 2015-2022
    • Xie, W.1    Tanabe, G.2    Akaki, J.3    Morikawa, T.4    Ninomiya, K.5    Minematsu, T.6    Yoshikawa, M.7    Wu, X.8    Muraoka, O.9
  • 38
    • 2042546805 scopus 로고
    • 5-Thio-D-mannose from the marine sponge Clathria pyramida (Lendenfeld) the first example of a naturally occurring 5-thiosugar
    • Capon, R. J.; MacLeod, J. K. 5-Thio-D-mannose from the marine sponge Clathria pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar J. Chem. Soc., Chem. Commun. 1987, 15, 1200-1201
    • (1987) J. Chem. Soc., Chem. Commun. , vol.15 , pp. 1200-1201
    • Capon, R.J.1    Macleod, J.K.2
  • 39
    • 0037463799 scopus 로고    scopus 로고
    • α-Selective glycosylation with 5-thioglucopyranosyl donors; Synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units
    • Matsuda, H.; Ohara, K.; Morii, Y.; Hashimoto, M.; Miyairi, K.; Okuno, T. α-Selective glycosylation with 5-thioglucopyranosyl donors; synthesis of an IsoMaltotetraoside mimic composed of 5-thioglucopyranose units Bioorg. Med. Chem. Lett. 2003, 13, 1063-1066
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1063-1066
    • Matsuda, H.1    Ohara, K.2    Morii, Y.3    Hashimoto, M.4    Miyairi, K.5    Okuno, T.6
  • 40
    • 0000553472 scopus 로고    scopus 로고
    • Design and synthesis of potential inhibitors of Golgi endo-α-mannosidase: 5-thio-D-glucopyranosyl-α(1→3)-1-deoxymannojirimycin and methyl 5-thio-D-glucopyranosyl-α(1→3)-5-thio-α-D-mannopyranoside
    • Izumi, M.; Suhara, Y.; Ichikawa, Y. Design and synthesis of potential inhibitors of Golgi endo-α-mannosidase: 5-thio-D-glucopyranosyl-α(1→3)-1-deoxymannojirimycin and methyl 5-thio-D-glucopyranosyl-α(1→3)-5-thio-α-D-mannopyranoside J. Org. Chem. 1998, 63, 4811-4816
    • (1998) J. Org. Chem. , vol.63 , pp. 4811-4816
    • Izumi, M.1    Suhara, Y.2    Ichikawa, Y.3
  • 41
    • 0001472917 scopus 로고
    • Chemical-enzymic synthesis of 5′-thio-N-acetyllactosamine: The first disaccharide with sulfur in the ring of the non-reducing sugar
    • Yuasa, H.; Hindsgaul, O.; Palcic, M. Chemical-enzymic synthesis of 5′-thio-N-acetyllactosamine: the first disaccharide with sulfur in the ring of the non-reducing sugar J. Am. Chem. Soc. 1992, 114, 5891-5892
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5891-5892
    • Yuasa, H.1    Hindsgaul, O.2    Palcic, M.3
  • 42
    • 0027973188 scopus 로고
    • Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides
    • Mehta, S.; Jordan, K. L.; Weimar, T.; Kreis, U. C.; Batchelor, R. J.; Einstein, F. W. B.; Pinto, B. M. Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides Tetrahedron: Asymmetry 1994, 5, 2367-2396
    • (1994) Tetrahedron: Asymmetry , vol.5 , pp. 2367-2396
    • Mehta, S.1    Jordan, K.L.2    Weimar, T.3    Kreis, U.C.4    Batchelor, R.J.5    Einstein, F.W.B.6    Pinto, B.M.7
  • 43
    • 0028972506 scopus 로고
    • Synthesis and enzymic activity of novel glycosidase inhibitors containing sulfur and selenium
    • Mehta, S.; Andrews, J. S.; Johnston, B. D.; Svensson, B.; Pinto, B. M. Synthesis and enzymic activity of novel glycosidase inhibitors containing sulfur and selenium J. Am. Chem. Soc. 1995, 117, 9783-9790
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9783-9790
    • Mehta, S.1    Andrews, J.S.2    Johnston, B.D.3    Svensson, B.4    Pinto, B.M.5
  • 44
    • 0030972056 scopus 로고    scopus 로고
    • Synthesis of 5-thio-L-fucose-containing disaccharides, as sequence-specific inhibitors, and 2′-fucosyllactose, as a substrate of α-L-fucosidases
    • Izumi, M.; Tsuruta, O.; Harayama, S.; Hashimoto, H. Synthesis of 5-thio-L-fucose-containing disaccharides, as sequence-specific inhibitors, and 2′-fucosyllactose, as a substrate of α-L-fucosidases J. Org. Chem. 1997, 62, 992-998
    • (1997) J. Org. Chem. , vol.62 , pp. 992-998
    • Izumi, M.1    Tsuruta, O.2    Harayama, S.3    Hashimoto, H.4
  • 45
    • 2342460209 scopus 로고    scopus 로고
    • Practical synthesis of KRN7000 from phytosphingosine
    • Song, S.; Lee, T.; Jung, S.; Kim, D. Practical synthesis of KRN7000 from phytosphingosine Synthesis 2004, 6, 847-850
    • (2004) Synthesis , vol.6 , pp. 847-850
    • Song, S.1    Lee, T.2    Jung, S.3    Kim, D.4
  • 46
    • 84880202712 scopus 로고    scopus 로고
    • Synthesis of 5-thio-D-galactopyranose
    • Wang, Y.; Du, Y. Synthesis of 5-thio-D-galactopyranose J. Carbohydr. Chem. 2013, 32, 240-248
    • (2013) J. Carbohydr. Chem. , vol.32 , pp. 240-248
    • Wang, Y.1    Du, Y.2
  • 47
    • 0009702305 scopus 로고
    • Synthesis of dibenzyl glycosyl phosphites using dibenzyl N,N-diethylphosphoramidite as phosphitylating reagent: An effective route to glycosyl phosphates, nucleotides, and glycosides
    • Sim, M. M.; Kondo, H.; Wong, C. H. Synthesis of dibenzyl glycosyl phosphites using dibenzyl N,N-diethylphosphoramidite as phosphitylating reagent: an effective route to glycosyl phosphates, nucleotides, and glycosides J. Am. Chem. Soc. 1993, 115, 2260-2267
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2260-2267
    • Sim, M.M.1    Kondo, H.2    Wong, C.H.3
  • 48
    • 0035159618 scopus 로고    scopus 로고
    • Costimulation-dependent modulation of experimental autoimmune encephalomyelitis by ligand stimulation of Vα14 NK T cells
    • Pál, E.; Tabira, T.; Kawano, T.; Taniguchi, M.; Miyake, S.; Yamamura, T. Costimulation-dependent modulation of experimental autoimmune encephalomyelitis by ligand stimulation of Vα14 NK T cells J. Immunol. 2001, 166, 662-668
    • (2001) J. Immunol. , vol.166 , pp. 662-668
    • Pál, E.1    Tabira, T.2    Kawano, T.3    Taniguchi, M.4    Miyake, S.5    Yamamura, T.6
  • 49
    • 0035445493 scopus 로고    scopus 로고
    • Quantitative and Qualitative Analysis of the Balance between Type 1 and Type 2 Cytokine-producing CD8- and CD8+ T Cells in Systemic Lupus Erythematosus
    • Amel-Kashipaz, M. R.; Huggins, M. L.; Lanyon, P.; Robins, A.; Todd, I.; Powell, R. J. Quantitative and Qualitative Analysis of the Balance Between Type 1 and Type 2 Cytokine-producing CD8- and CD8+ T Cells in Systemic Lupus Erythematosus J. Autoimmun. 2001, 17, 155-163
    • (2001) J. Autoimmun. , vol.17 , pp. 155-163
    • Amel-Kashipaz, M.R.1    Huggins, M.L.2    Lanyon, P.3    Robins, A.4    Todd, I.5    Powell, R.J.6


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