Glycolipids as immunostimulating agents

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 3, 2008, Pages 1073-1083

  Wu, Douglass ^a   Fujio, Masakazu ^a   Wong, Chi Huey ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

Galactosyl ceramide analogs; CD1d; Glycolipid

Indexed keywords

AGELASPHIN DERIVATIVE; ALPHA C GALACTOSYLCERAMIDE; ALPHA GALACTOSYLCERAMIDE; ALPHA GALACTOSYLCERAMIDE DERIVATIVE; ALPHA GLUCOSYLCERAMIDE; ALPHA MANNOSYLCERAMIDE; BETA GALACTOSYLCERAMIDE; DISACCHARIDE; GALACTOFURANOSE BETA1 3 GALACTOSE ALPHA1 1' CEREMIDE; GALACTOSE; GALACTOSE ALPHA1 2 GALACTOSYLCERAMIDE; GALACTOSE ALPHA1 3 GALACTOSYLCERAMIDE; GALACTOSE ALPHA1 6 GALACTOSYLCERAMIDE; GALACTOSE APHA1 2 GALACTOSE ALPHA1 1' CERAMIDE; GALACTOSE APHA1 4 GLUCOSE BETA1 1' CERAMIDE; GALACTOSE APHA1 6 GALACTOSE ALPHA1 1' CERAMIDE; GALACTOSE APHA1 6 GLUCOSE ALPHA1 1' CERAMIDE; GLYCOLIPID; GLYCOSPHINGOLIPID; IMMUNOSTIMULATING AGENT; PHYTOSPHINGOSINE; T LYMPHOCYTE ANTIGEN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIGEN PRESENTING CELL; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; BACTERIAL INFECTION; BREAST CANCER; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; HEPATITIS B; HUMAN; IMMUNE RESPONSE; LUNG CANCER; MALARIA; MELANOMA; NATURAL KILLER T CELL; NEOPLASM; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; T LYMPHOCYTE ACTIVATION; TH1 CELL;

ANIMALS; ANTIGENS, CD1; GALACTOSYLCERAMIDES; GLYCOLIPIDS; HUMANS; IMMUNOASSAY; MODELS, IMMUNOLOGICAL;

EID: 38849154570     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.10.026     Document Type: Review

References (81)

1. Brigl M., and Brenner M.B. Annu. Rev. Immunol. 22 (2004) 817-890
2. Porcelli S.A., and Modlin R.L. Annu. Rev. Immunol. 17 (1999) 297-329
3. Savage P.B., Teyton L., and Bendelac A. Chem. Soc. Rev. 35 (2007) 771-779
4. Calabi F., Jarvis J.M., Martin L., and Milstein C. Eur. J. Immunol. 19 (1989) 285-292
5. Porcelli S. Adv. Immunol. 59 (1995) 1-98
6. Zajonc D.M., Elsliger M.A., Teyton L., and Wilson I.A. Nat. Immunol. 4 (2003) 808-815
7. Zajonc D.M., Crispin M.D.M., Bowden T.A., Young D.C., Cheng T.Y., Hu J.D., Costello C.E., Rudd P.M., Dwek R.A., Miller M.J., Brenner M.B., Moody D.B., and Wilson I.A. Immunity 22 (2005) 209-219
8. Batuwangala T., Shepherd D., Gadola S.D., Gibson K.J.C., Zaccai N.R., Fersht A.R., Besra G.S., Cerundolo V., and Jones E.Y. J. Immunol. 172 (2004) 2382-2388
9. Gadola S.D., Zaccai N.R., Harlos K., Shepherd D., Castro-Palomino J.C., Ritter G., Schmidt R.R., Jones E.Y., and Cerundolo V. Nat. Immunol. 3 (2002) 721-726
10. Koch M., Stronge V.S., Shepherd D., Gadola S.D., Mathew B., Ritter G., Fersht A.R., Besra G.S., Schmidt R.R., Jones E.Y., and Cerundolo V. Nat. Immunol. 6 (2005) 819-826
11. Zeng Z.-H., Castano A.R., Segelke B.W., Stura E.A., Peterson P.A., and Wilson I.A. Science 277 (1997) 339-345
12. Zajonc D.M., Maricic I., Wu D., Halder R., Roy K., Wong C.-H., Kumar V., and Wilson I.A. J. Exp. Med. 202 (2005) 1517-1526
13. Zajonc D.M., Cantu C., Mattner J., Zhou D., Savage P.B., Bendelac A., Wilson I.A., and Teyton L. Nat. Immunol. 6 (2005) 810-818
14. Giabbai B., Sidobre S., Crispin M.D.M., Sanchez-Ruiz Y., Bachi A., Kronenberg M., Wilson I.A., and Degano M. J. Immunol. 175 (2005) 977-984
15. Zajonc D.M., Ainge G.D., Painter G.F., Severn W.B., and Wilson I.A. J. Immunol. 177 (2006) 4577-4583
16. Borg N.A., Wun K.S., Kjer-Nielsen L., Wilce M.C.J., Pellicci D.G., Koh R., Besra G.S., Bharadwaj M., Godfrey D.I., McCluskey J., and Rossjohn J. Nature 448 (2007) 44-49
17. De Libero G., and Mori L. Nat. Rev. Immunol. 5 (2005) 485-496
18. Morita M., Motoki K., Akimoto K., Natori T., Sakai T., Sawa E., Yamaji K., Koezuka Y., Kobayashi E., and Fukushima H. J. Med. Chem. 38 (1995) 2176-2187
19. Natori T., Koezuka Y., and Higa T. Tetrahedron Lett. 34 (1993) 5591-5592
20. Natori T., Morita M., Akimoto K., and Koezuka Y. Tetrahedron 50 (1994) 2771-2784
21. Kawano T., Cui J., Koezuka Y., Toura I., Kaneko Y., Sato H., Kondo E., Harada M., Koseki H., Nakayama T., Tanaka Y., and Taniguchi M. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 5690-5693
22. Nicol A., Nieda M., Koezuka Y., Porcelli S., Suzuki K., Tadokoro K., Durrant S., and Juji T. Immunology 99 (2000) 229-234
23. Chang D.H., Osman K., Connolly J., Kukreja A., Krasovsky J., Pack M., Hutchinson A., Geller M., Liu N., Annable R., Shay J., Kirchhoff K., Nishi N., Ando Y., Hayashi K., Hassoun H., Steinman R.M., and Dhodapkar M.V. J. Exp. Med. 201 (2005) 1503-1517
24. Gonzalez-Aseguinolaza G., Van Kaer L., Bergmann C.C., Wilson J.M., Schmieg J., Kronenberg M., Nakayama T., Taniguchi M., Koezuka Y., and Tsuji M. J. Exp. Med. 195 (2002) 617-624
25. Takeda K., Hayakawa Y., Van Kaer L., Matsuda H., Yagita H., and Okumura K. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 5498-5503
26. Skold M., and Behar S.M. Infect. Immun. 71 (2003) 5447-5455
27. Skold M., and Behar S.M. Microbes Infect. 7 (2005) 544-551
28. Kaer L.V. Nat. Rev. Immunol. 5 (2005) 31-42
29. Silk J.D., Hermans I.F., Gileadi U., Chong T.W., Shepherd D., Salio M., Mathew B., Schmidt R.R., Lunt S.J., Williams K.J., Stratford I.J., Harris A.L., and Cerundolo V. J. Clin. Invest. 114 (2004) 1800-1811
30. Kawano T., Cui J., Koezuka Y., Toura I., Kaneko Y., Motoki K., Ueno H., Nakagawa R., Sato H., Kondo E., Koseki H., and Taniguchi M. Science 278 (1997) 1626-1629
31. Chen H., and Paul W. J. Immunol. 159 (1997) 2240-2249
32. Stetson D.B., Mohrs M., Reinhardt R.L., Baron J.L., Wang Z.-E., Gapin L., Kronenberg M., and Locksley R.M. J. Exp. Med. 198 (2003) 1069-1076
33. Carnaud C., Lee D., Donnars O., Park S.-H., Beavis A., Koezuka Y., and Bendelac A. J. Immunol. 163 (1999) 4647-4650
34. Eberl G., Brawand P., and MacDonald H.R. J. Immunol. 165 (2000) 4305-4311
35. Eberl G., and MacDonald H.R. Eur. J. Immunol. 30 (2000) 985-992
36. Smyth M.J., Crowe N.Y., Pellicci D.G., Kyparissoudis K., Kelly J.M., Takeda K., Yagita H., and Godfrey D.I. Blood 99 (2002) 1259-1266
37. Hayakawa Y., Godfrey D.I., and Smyth M.J. Curr. Med. Chem. 11 (2004) 241-252
38. Van Kaer L. Immunol. Cell Biol. 82 (2004) 315-322
39. Mosmann T.R., and Sad S. Immunol. Today 17 (1996) 138-146
40. Romagnani S. Immunol. Today 18 (1997) 263-266
41. Steinman L. Neuron 24 (1999) 511-514
42. Muhammad Ali Tahir S., Cheng O., Shaulov A., Koezuka Y., Bubley G.J., Wilson S.B., Balk S.P., and Exley M.A. J. Immunol. 167 (2001) 4046-4050
43. Wilson S.B., and Delovitch T.L. Nat. Rev. Immunol. 3 (2003) 211-222
44. Giaccone G., Punt C.J.A., Ando Y., Ruijter R., Nishi N., Peters M., von Blomberg B.M.E., Scheper R.J., van der Vliet H.J.J., van den Eertwegh A.J.M., Roelvink M., Beijnen J., Zwierzina H., and Pinedo H.M. Clin. Cancer Res. 8 (2002) 3702-3709
45. Goff R.D., Gao Y., Mattner J., Zhou D., Yin N., Cantu C., Teyton L., Bendelac A., and Savage P.B. J. Am. Chem. Soc. 126 (2004) 13602-13603
46. Miyamoto K., Miyake S., and Yamamura T. Nature 413 (2001) 531-534
47. Singh A.K., Wilson M.T., Hong S., Olivares-Villagomez D., Du C., Stanic A.K., Joyce S., Sriram S., Koezuka Y., and Van Kaer L. J. Exp. Med. 194 (2001) 1801-1811
48. Yu K.O.A., Im J.S., Molano A., Dutronc Y., Illarionov P.A., Forestier C., Fujiwara N., Arias I., Miyake S., Yamamura T., Chang Y.-T., Besra G.S., and Porcelli S.A. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 3383-3388
49. Yang G., Schmieg J., Tsuji M., and Franck R.W. Angew. Chem. Int. Ed. Engl. 43 (2004) 3818-3822
50. Schmieg J., Yang G., Franck R.W., and Tsuji M. J. Exp. Med. 198 (2003) 1631-1641
51. Prigozy T.I., Naidenko O., Qasba P., Elewaut D., Brossay L., Khurana A., Natori T., Koezuka Y., Kulkarni A., and Kronenberg M. Science 291 (2001) 664-667
52. Wu D., Xing G.W., Poles M.A., Horowitz A., Kinjo Y., Sullivan B., Bodmer-Narkevitch V., Plettenburg O., Kronenberg M., Tsuji M., Ho D.D., and Wong C.H. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 1531-1536
53. Xing G.W., Wu D., Poles M.A., Horowitz A., Tsuji M., Ho D.D., and Wong C.H. Bioorg. Med. Chem. 13 (2005) 2907-2916
54. Liu Y., Goff R.D., Zhou D., Mattner J., Sullivan B.A., Khurana A., Cantu III C., Ravkov E.V., Ibegbu C.C., Altman J.D., Teyton L., Bendelac A., and Savage P.B. J. Immunol. Methods 312 (2006) 34-39
55. Zhou X.T., Forestier C., Goff R.D., Li C., Teyton L., Bendelac A., and Savage P.B. Org. Lett. 4 (2002) 1267-1270
56. Kinjo Y., Wu D., Kim G., Xing G.W., Poles M.A., Ho D.D., Tsuji M., Kawahara K., Wong C.H., and Kronenberg M. Nature 434 (2005) 520-525
57. Sidobre S., Hammond K.J.L., Bénazet-Sidobre L., Maltsev S.D., Richardson S.K., Ndonye R.M., Howell A.R., Sakai T., Besra G.S., Porcelli S.A., and Kronenberg M. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 12254-12259
58. Lee T., Cho M., Ko S.Y., Youn H.J., Baek D.J., Cho W.J., Kang C.Y., and Kim S. J. Med. Chem. 50 (2007) 585-589
59. Wu D., Zajonc D.M., Fujio M., Sullivan B.A., Kinjo Y., Kronenberg M., Wilson I.A., and Wong C.H. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 3972-3977
60. Franchini L., Matto P., Ronchetti F., Panza L., Barbieri L., Costantino V., Mangoni A., Cavallari M., Mori L., and De Libero G. Bioorg. Med. Chem. 15 (2007) 2236-5529
61. Fan G.T., Pan Y.S., Lu K.C., Cheng Y.P., Lin W.C., Lin S., Lin C.H., Wong C.H., Fang J.M., and Lin C.C. Tetrahedron 61 (2005) 1855-1862
62. Fischer K., Scotet E., Niemeyer M., Koebernick H., Zerrahn J., Maillet S., Hurwitz R., Kursar M., Bonneville M., Kaufmann S.H.E., and Schaible U.E. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 10685-10690
63. Rauch J., Gumperz J., Robinson C., Skold M., Roy C., Young D.C., Lafleur M., Moody D.B., Brenner M.B., Costello C.E., and Behar S.M. J. Biol. Chem. 278 (2003) 47508-47515
64. Tsuji M. Cell. Mol. Life Sci. 63 (2006) 1889-1898
65. Kinjo Y., Tupin E., Wu D., Fujio M., Garcia-Navarro R., Benhnia M.R.-E.-I., Zajonc D.M., Ben-Menachem G., Ainge G.D., Painter G.F., Khurana A., Hoebe K., Behar S.M., Beutler B., Wilson I.A., Tsuji M., Sellati T.J., Wong C.-H., and Kronenberg M. Nat. Immunol. 7 (2006) 978-986
66. Berkers C.R., and Ovaa H. Trends Pharmacol. Sci. 26 (2005) 252-257
67. Fujio M., Wu D., Garcia-Navarro R., Ho D.D., Tsuji M., and Wong C.H. J. Am. Chem. Soc. 128 (2006) 9022-9023
68. Chang Y.-J., Huang J.-R., Tsai Y.-C., Hung J.-T., Wu D., Fujio M., Wong C.-H., and Yu A.L. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 10299-10304
69. Cantu III C., Benlagha K., Savage P.B., Bendelac A., and Teyton L. J. Immunol. 170 (2003) 4673-4682
70. Zhou D., Mattner J., Cantu III C., Schrantz N., Yin N., Gao Y., Sagiv Y., Hudspeth K., Wu Y.-P., Yamashita T., Teneberg S., Wang D., Proia R.L., Levery S.B., Savage P.B., Teyton L., and Bendelac A. Science 306 (2004) 1786-1789
71. Neef A., Witzenberger R., and Kampfer P. J. Ind. Microbiol. Biotechnol. 23 (1999) 261-267
72. Kawahara K., Moll H., Knirel Y.A., Seydel U., and Zahringer U. Eur. J. Biochem. 267 (2000) 1837-1846
73. Kawahara K., Seydel U., Matsuura M., Danbara H., Rietschel E.T., and Zahringer U. FEBS Lett. 292 (1991) 107-110
74. Kawasaki S., Moriguchi R., Sekiya K., Nakai T., Ono E., Kume K., and Kawahara K. J. Bacteriol. 176 (1994) 284-290
75. Steere A.C. N. Engl. J. Med. 345 (2001) 115-125
76. Orlosk i.K., Hayes E., Campbell G., and Dennis D. Mor. Mortal. Wkly. Rep. CDC Surveill. Summ. 49 (2000) 1-11
77. Kumar H., Belperron A., Barthold S.W., and Bockenstedt L.K. J. Immunol. 165 (2000) 4797-4801
78. Belperron A.A., Dailey C.M., and Bockenstedt L.K. J. Immunol. 174 (2005) 5681-5686
79. Ben-Menachem G., Kubler-Kielb J., Coxon B., Yergey A., and Schneerson R. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 7913-7918
80. Agea E., Russano A., Bistoni O., Mannucci R., Nicoletti I., Corazzi L., Postle A.D., De Libero G., Porcelli S.A., and Spinozzi F. J. Exp. Med. 202 (2005) 295-308
81. Takayama K., Rothenberg R., and Barbour A. Infect. Immun. 55 (1987) 2311-2313