Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY α-Galactosylceramide

ChemBioChem

Volumn 4, Issue 1, 2003, Pages 27-33

  Vo Hoang, Yen ^a   Micouin, Laurent ^a   Ronet, Catherine ^b   Gachelin, Gabriel ^b   Bonin, Martine ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b INSERM   (France)

Author keywords

Asymmetric synthesis; Fluorescent probes; Glycolipids; Immunoregulation; Natural killer T cells

Indexed keywords

1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; ALPHA GALACTOSYLCERAMIDE; BORON DIPYRROMETHENE DIFLUORIDE; CARBOHYDRATE; FLUORESCENT DYE; FLUORIDE; GALACTOSYLCERAMIDE; GAMMA INTERFERON; GLYCOLIPID; INTERLEUKIN 4; T LYMPHOCYTE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ANTIGEN PRESENTING CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; AUTOIMMUNE DISEASE; ENANTIOSELECTIVITY; FLUORESCENCE; IMMUNOREGULATION; KUPFFER CELL; LIVER CELL; MACROPHAGE; MOUSE; NATURAL KILLER CELL; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS; T LYMPHOCYTE;

ANIMALS; CELL ADHESION; FLOW CYTOMETRY; FLUORESCENCE; FLUORESCENT DYES; GALACTOSYLCERAMIDES; GLYCOLIPIDS; IMAGE PROCESSING, COMPUTER-ASSISTED; INDICATORS AND REAGENTS; INJECTIONS, INTRAPERITONEAL; INJECTIONS, INTRAVENOUS; KILLER CELLS, NATURAL; LIVER; MICE; MICE, INBRED C57BL; MOLECULAR CONFORMATION; SPLEEN; STEREOISOMERISM;

ANIMALIA;

EID: 0037415043     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200390009     Document Type: Article

References (34)

1. a) Y. Koezuka, K. Kabaya, K. Motoki (Kirin Beer Kabushiki Kaisha), US Patent 6071884, 2000,
2. b) O. Plettenburg, V. Bodmer-Narkevitch, C.-H. Wong, J. Org. Chem. 2002, 67, 4559-4564 and references cited therein.
3. D. I. Godfrey, K. J. Hammond, L. D. Poulton, M. J. Smyth, A. G. Baxter, Immunol. Today 2000, 21, 573-583.
4. Z. Illes, T. Kondo, J. Newcombe, N. Oka, T. Tabira, T. Yamamura, J. Immunol. 2000, 164, 4375-4381.
5. a) S. Sharif, G. A. Arreaza, P. Zucker, Q. S. Mi, J. Sondhi, O. V. Naidenko, M. Kronenberg, Y. Koezuka; T. L. Delovitch, J. M. Leite-de-Morales, C. Gouarin, R. Zhu, A. Hameg, T. Nakayama, M. Taniguchi, F. Lepault, A. Lehuen, J. F. Bach, A. Herbelin, Nat. Med. 2001, 1057-1062;
6. b) Y. N. Naumov, K. S. Bahjat, S. B. Wilson, Proc. Nat. Acad. Sci. USA 2001, 98, 13838-13843.
7. a) A. W. Jahng, I. Maricic, B. Pedersen, N. Burdin, O. Naidenko, M. Kronenberg Y. Koezuka, V. Kumar, J. Exp. Med. 2001, 194, 1789-1799;
8. b) K. Miyamoto, S. Miyake, T. Yamamura, Nature 2001, 413, 531-534.
9. a) M. J. Smyth, N. Y. Crowe, Y. Hayakawa, H. Takeda, H. Yagita, D. I. Godfrey, Curr. Opin. Immunol. 2002, 14, 165-171;
10. b) C. Stremmel, M. Exley, S. Balk, W. Hohenberger, V.K. Kuchroo, Eur. J. Immunol. 2001, 31, 2818-2828;
11. c) M. J. Smyth, D.I. Godfrey, Nat. Immunol. 2000, 1, 459-460;
12. d) T. Kawano, J. Cui, Y. Koezuka, Science 1997, 278, 1626-1629.
13. K. Seino, K. Fukao, K. Muramoto, K. Yanagisawa, Y. Takada, S. Kakuta, Y. Iwakura, L. Van Kaer, K. Takeda, T. Nakayama, M. Taniguchi, H. Bashuda, H. Yagita, K. Okumura, Proc. Natl. Acad. Sci. USA 2001, 98, 2577-2581.
14. M. A. Ostos, D. Recalde, M. M. Zakin, D. Scott-Algara, FEBS Lett. 2002, 519, 23-29.
15. T. Natori, Y. Koezuka, T. Higa, Tetrahedron Lett. 1993, 34, 5591-5592.
16. M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, H. Kukushima, J. Med. Chem. 1995, 38, 2176-2187.
17. In parallel with our studies, recent results report the synthesis of fluorophore and biotin-labelled C6" α-GalCer derivatives and the retention of NKT cell-stimulating properties these compounds achieve: X.-T. Zhou, C. Forestier, R. D. Goff, C. Li, L. Teyton, A. Bendelac, P. B. Savage, Org. Lett. 2002, 4, 1267-1270.
18. a) T. Sakai, O. V. Naidenko, H. Iijima, M. Kronenberg, Y. Koezuka, J. Med. Chem. 1999, 42, 1836-1841;
19. b) O. V. Naidenko, J. K. Maher, W. A. Ernst, T. Sakai, R. L. Modlin, M. Kronenberg, J. Exp. Med. 1999, 190, 1069-1079.
20. a) T. Sakai, H. Ehara, Y. Koezuka, Org. Lett. 1999, 1, 359-361;
21. b) L. J. Saubermann, P. Beck, Y. P. de Jong, R. S. Pitman, M. S. Ryan, H. S. Kim, M. Exley, S. Snapper, S. P. Balk, S. J. Hagen, O. Kanauchi, K. Motoki, T. Sakai, C. Terhorst, Y. Koezuka, D. K. Podolsky, R. S. Blumberg, Gastroenterology 2000, 119, 119-128.
22. R. E. Pagano, R. Watanabe, C. Wheatley, M. Dominguez, in Methods in Enzymology, Vol. 312 (Eds.: A. H. Merrill, Jr., Y. A. Hannun), Academic Press, San Diego, 2000, pp. 523-534.
23. a) T. Sakai, M. Morita, N. Matsunaga, K. Akimoto, T. Yokoyama, H. Iijima, Y. Koezuka, Bioorg. Med. Chem. Lett. 1999, 9, 697-702;
24. b) H. Iijima, K. Kimura, T. Sakai, A. Ichimura, T. Shimizu, H. Ueno, T. Natori, Y. Koezuka, Bioorg. Med. Chem. 1998, 6, 1905-1910;
25. c) A. Uchimura, T. Shimizu, M. Morita, H. Ueno, K. Motoki, H. Fukushima, T. Natori, Y. Koezuka, Bioorg. Med. Chem. 1997, 5, 2245-2249.
26. Y. Vo-Hoang, M. Bonin, L. Micouin, G. Gachelin, (Institut Pasteur, INSERM, CNRS) Fr Patent 0205557, 2002.
27. A. Solladie-Cavallo, J. L. Koessler, J. Org. Chem. 1994, 59, 3240-3242.
28. a) K. C. Nicolaou, T. Caulfield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 1988, 110, 7910-7912;
29. b) T. Mukaiyama, Y. Murai, S. Shoda, Chem. Lett. 1981, 431-432.
30. a) G. Eberl, H. R. MacDonald, Eur. J. Immunol. 2000, 30, 985-992;
31. b) M. C. Leite-de-Morales, A. Herbelin, C. Gouarin, Y. Koezuka, E. Schneider, M. Dy, J. Immunol. 2000, 165, 4367-4371;
32. c) Y. Osman, T. Kawamura, T. Naito, K. Takeda, L. van Kaer, K. Okumura, T. Abo, Eur. J. Immunol. 2000, 30, 1919-1928.
33. a) N. Burdin, L. Brossay, M. Kronenberg, Eur. J. Immunol. 1999, 29, 2014-2025;
34. b) N. Singh, S. Hong, D. C. Scherer, I. Serizawa, N. Burdin, M. Kronenberg, Y. Koezuka, L. Van Kaer, J. Immunol. 1999, 163, 2373-2377.