Synthesis and evaluation of an α-C-galactosylceramide analogue that induces Th1-biased responses in human natural killer T cells

ChemBioChem

Volumn 7, Issue 11, 2006, Pages 1750-1756

  Lu, Xuequan ^a   Song, Liping ^b   Metelitsa, Leonid S ^b   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

Cytokines; Glycolipids; Immune agents; Immunology; Lipids

Indexed keywords

ALPHA GALACTOSYLCERAMIDE; GAMMA INTERFERON; GLYCOSIDE; INTERLEUKIN 13; INTERLEUKIN 4;

ANTIGEN PRESENTING CELL; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DENDRITIC CELL; HUMAN; HUMAN CELL; IMMUNE RESPONSE; IMMUNOSTIMULATION; IN VITRO STUDY; NATURAL KILLER T CELL; PRIORITY JOURNAL; T LYMPHOCYTE ACTIVATION;

CELLS, CULTURED; CYTOKINES; DENDRITIC CELLS; GALACTOSYLCERAMIDES; GLYCOSYLATION; HUMANS; MOLECULAR STRUCTURE; T-LYMPHOCYTES, REGULATORY; TH1 CELLS;

EID: 33751011895     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200600197     Document Type: Article

References (48)

1. D. I. Godfrey, M. Kronenberg, J. Clin. Invest. 2004, 114, 1379-1388.
2. L. Van Kaer, S. Joyce, Curr. Biol. 2005, 15, R429-R431.
3. T. Kawano, J. Cui, Y. Koezuka, I. Toura, Y. Kaneko, K. Motoki, H. Ueno, R. Nakagawa, H. Sato, E. Kondo, H. Koseki, M. Taniguchi, Science 1997, 278, 1626-1629.
4. L. Brossay, M. Chioda, N. Burdin, Y. Koezuka, G. Casorati, P. Dellabona, M. Kronenberg, J. Exp. Med. 1998, 188, 1521-1528.
5. S. Porcelli, C. E. Yockey, M. B. Brenner, S. P. Balk, J. Exp. Med. 1993, 178, 1-16.
6. O. Lantz, A. Bendelac, J. Exp. Med. 1994, 180, 1097-1106.
7. A. Bendelac, O. Lantz, M. E. Quimby, J. W. Yewdell, J. R. Bennink, R. R. Brutkiewicz, Science 1995, 268, 863-865.
8. A. Bendelac, M. N. Rivera, S. H. Park, J. H. Roark, Annu. Rev. Immunol. 1997, 15, 535-562.
9. D. I. Godfrey, K. J. Hammond, L. D. Poulton, M. J. Smyth, A. G. Baxter, Immunol. Today 2000, 21, 573-583.
10. M. Kronenberg, Annu. Rev. Immunol. 2005, 23, 877-900.
11. L. Van Kaer, Nat. Rev. Immunol. 2005, 5, 31-42.
12. R. Nakagawa, K. Motoki, H. Ueno, R. Iijima, H. Nakamura, E. Kobayashi, A. Shimosaka, Y. Koezuka, Cancer Res. 1998, 58, 1202-1207.
13. I. Toura, T. Kawano, Y. Akutsu, T. Nakayama, T. Ochiai, M. Taniguchi, J. Immunol. 1999, 163, 2387-2391.
14. R. Nakagawa, I. Serizawa, K. Motoki, M. Sato, H. Ueno, R. Iijima, H. Nakamura, A. Shimosaka, Y. Koezuka, Oncol. Res. 2000, 12, 51-58.
15. M. J. Smyth, E. Cretney, K. Takeda, R. H. Wiltrout, L. M. Sedger, N. Kayagaki, H. Yagita, K. Okumura, J. Exp. Med. 2001, 193, 661-670.
16. M. Koch, V. S. Stronge, D. Shepherd, S. D. Gadola, B. Mathew, G. Ritter, A. R. Fersht, G. S. Besra, R. R. Schmidt, E. Y. Jones, V. Cerundolo, Nat. Immunol. 2005, 6, 819-826.
17. D. M. Zajonc, C. Cantu, III, J. Mattner, D. Zhou, P. B. Savage, A. Bendelac, I. A. Wilson, L. Teyton, Nat. Immunol. 2005, 6, 810-818.
18. J. Schmieg, G. Yang, R. W. Franck, M. Tsuji, J. Exp. Med. 2003, 198, 1631-1641.
19. G. Yang, J. Schmieg, M. Tsuji, R. W. Franck, Angew. Chem. 2004, 116, 3906-3910;
20. Angew. Chem. Int. Ed. 2004, 43, 3818-3822.
21. M. Tsuji, Cell. Mol. Life Sci. 2006, 1, 1-10.
22. G. Chen, M. Chien, M. Tsuji, R. W. Franck, ChemBioChem 2006, 7, 1017-1022.
23. G. Chen, J. Schmieg, M. Tsuji, R. W. Franck, Org. Lett. 2004, 6, 4077-4080.
24. H. Tomiyama, T. Yanagisawa, M. Nimura, A. Noda, T. Tomiyama, Ger. Offen. DE 10128250, 2001 [Chem. Abstr. 2001, 136, 37901];
25. H. Tomiyama, T. Yanagisawa, M. Nimura, A. Noda, T. Tomiyama, US Patent 6 635 622, 2001.
26. T. Toba, K. Murata, T. Yamamura, S. Miyake, H. Annoura, Tetrahedron Lett. 2005, 46, 5043-5047.
27. V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 6237-6240.
28. M. D. Lewis, J. K. Cha, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 4976-4978.
29. A. Giannis, K. Sandhoff, Tetrahedron Lett. 1985, 26, 1479-1482.
30. K. C. Nicolaou, C. K. Hwang, M. E. Duggan, J. Am. Chem. Soc. 1989, 111, 6682-6690.
31. J. S. Panek, M. A. Sparks, J. Org. Chem. 1989, 54, 2034-2038.
32. E. G. Nolen, M. M. Watts, D. J. Fowler, Org. Lett. 2002, 4, 3963-3965.
33. H. Tohma, Y. Kita, Adv. Synth. Catal. 2004, 346, 111-124.
34. T. Katsuki, V. S. Martin, Org. React. 1996, 48, 1-299.
35. C. H. Behrens, K. B. Sharpless, J. Org. Chem. 1985, 50, 5696-5704.
36. A. O. King, I. Shinkai in Encyclopedia of Reagents for Organic Synthesis (Ed.: L. A. Raquette), Wiley, Chichester, 1995, pp. 3888-3889.
37. K. Pihlaja, E. Kleinpeter, Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis, 1994, Wiley-VCH, New York, pp. 55-56.
38. M. J. Smyth, N. Y. Crowe, D. G. Pellicci, K. Kyparissoudis, J. M. Kelly, K. Takeda, H. Yagita, D. I. Godfrey, Blood 2002, 99, 1259-1266.
39. T. Takahashi, M. Nieda, Y. Koezuka, A. Nicol, S. A. Porcelli, Y. Ishikawa, K. Tadokoro, H. Hirai, T. Juji, J. Immunol. 2000, 164, 4458-4464.
40. L. S. Metelitsa, O. V. Naidenko, A. Kant, H. W. Wu, M. J. Loza, B. Perussia, M. Kronenberg, R. C. Seeger, J. Immunol. 2001, 167, 3114-3122.
41. J. Schmieg, G. Yang, R. W. Franck, N. Van Rooijen, M. Tsuji, Proc. Natl. Acad. Sci. USA 2005, 102, 1127-1132.
42. J. Chun, G. Li, H. S. Byun, R. Bittman, J. Org. Chem. 2002, 67, 2600-2605.
43. L. S. Metelitsa, Clin. Immunol. 2004, 110, 267-276.
44. D. H. Chang, K. Osman, J. Connolly, A. Kukreja, J. Krasovsky, M. Pack, A. Hutchinson, M. Geller, N. Liu, R. Annable, J. Shay, K. Kirchhoff, N. Nishi, Y. Ando, K. Hayashi, H. Hassoun, R. M. Steinman, M. V. Dhodapkar, J. Exp. Med. 2005, 201, 1503-1517.
45. N. L. Allinger, J. Am. Chem. Soc. 1977, 99, 8127-8134.
46. W. J. Hehre, A Guide to Molecular Mechanics and Quantum Chemical Calculations, 2003, Wavefunction, Irvine, CA.
47. W. J. Pietro, M. M. Francl, W. J. Hehre, D. J. Defrees, J. A. Pople, J. S. Binkley, J. Am. Chem. Soc. 1982, 104, 5039-5048.
48. P. J. Pulay, J. Comput. Chem. 1982, 3, 556-560.