The C-glycoside analogue of the immunostimulant α-galactosylceramide (KRN7000): Synthesis and striking enhancement of activity

Angewandte Chemie - International Edition

Volumn 43, Issue 29, 2004, Pages 3818-3822

  Yang, Guangli ^a   Schmieg, John ^b   Tsuji, Moriya ^b   Franck, Richard W ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b NEW YORK UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Biological activity; C glycosides; Drug design; Immunostimulants; Ramberg B cklund reaction

Indexed keywords

DIAGNOSIS; DRUG THERAPY; LIVING SYSTEMS STUDIES; MALARIA CONTROL; SYNTHESIS (CHEMICAL);

BIOLOGICAL ASSAYS; C-GLYCOSIDE; THERAPEUTIC AGENTS;

NITROGEN COMPOUNDS;

1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; ALPHA GALACTOSYLCERAMIDE; GLYCOSIDE; IMMUNOSTIMULATING AGENT; NATURAL PRODUCT; ANTINEOPLASTIC AGENT; C GLYCOSIDE; C-GLYCOSIDE; GALACTOSYLCERAMIDE; IMMUNOLOGICAL ADJUVANT; MONOSACCHARIDE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; MALARIA; MELANOMA; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ANIMAL; CYTOTOXICITY; DOSE RESPONSE; DRUG EFFECT; EXPERIMENTAL MELANOMA; IMMUNOLOGY; LIVER TUMOR; LUNG; METABOLISM; SPOROZOITE; SYNTHESIS;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; ANTINEOPLASTIC AGENTS; CYTOTOXICITY, IMMUNOLOGIC; DOSE-RESPONSE RELATIONSHIP, DRUG; GALACTOSYLCERAMIDES; LIVER NEOPLASMS, EXPERIMENTAL; LUNG; MELANOMA, EXPERIMENTAL; MICE; MONOSACCHARIDES; SPOROZOITES;

EID: 4444295929     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454215     Document Type: Article

References (51)

1. a) T. Natori, M. Morita, K. Akimoto, Y. Koezuka, Tetrahedron 1994, 50, 2771-2784;
2. b) similar substances have been isolated from Agelas Clathrodes by the Mangoni research group: V. Costantino, E. Fattorusso, C. Imperatore, A. Mangoni, J. Org. Chem. 2004, 69, 1174-1179, and references therein.
3. a) M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, H. Fukushima, J. Med. Chem. 1995, 38, 2176-2187;
4. b) Y. Vo-Hoang, L. Micouin, C. Ronet, G. Gachelin, M. Bonin, ChemBioChem 2003, 4, 27-33;
5. c) T. Sakai, O. Naidenko, H. Iijima, M. Kronenberg, Y. Koezuka, J. Med. Chem. 1999, 42, 1836-1841;
6. d) T. Sakai, H. Ehara, Y. Koezuka, Org. Lett. 1999, 1, 359-361;
7. e) X. T. Zhou, C. Forestier, R. D. Goff, C. Li, L. Teyton, A. Bendelac, P. B. Savage, Org. Lett. 2002, 4, 1267-1270;
8. f) T. Sakai, M. Morita, N. Matsunaga, K. Akimoto, T. Yokoyama, H. Iijima, Y. Koezuka, Bioorg. Med. Chem. Lett. 1999, 9, 697-702.
9. A. Kikuchi, M. Nieda, C. Schmidt, Y. Koezuka, S. Ishihara, Y. Ishikawa, K. Tadokoro, S. Durrant, A. Boyd, T. Juji, A. Nicol, Br. J. Cancer 2001, 85, 741-746.
10. G. Matsumoto, S. Nagai, M. Toi, S. Ishiyama, K. Kuroi, K. Turuta, A. Okamoto, T. Takahashi, Nippon Geka Gakkai Zasshi 2001, 102, 421.
11. R. Nakagawa, K. Motoki, H. Ueno, H. Iijima, H. Nakamura, E. Kobayashi, A. Shimosaka, Y. Koezuka, Cancer Res. 1998, 58, 1202-1207.
12. Y. Hayakawa, S. Rovero, G. Forni, M. J. Smyth, Proc. Natl. Acad. Sci. USA 2003, 100, 9464-9469.
13. G. Gonzalez-Aseguinolaza, C. de Oliveira, M. Tomaska, S. Hong, O. Bruna-Romero, T. Nakayama, M. Taniguchi, A. Bendelac, L. Van Kaer, Y. Koezuka, M. Tsuji, Proc. Natl. Acad. Sci. USA 2000, 97, 8461-8466.
14. a) S. Hong, M. T. Wilson, I. Serizawa, L. Wu, N. Singh, O. V. Naidenko, T. Miura, T. Haba, D. C. Scherer, J. Wei, M. Kronenberg, Y. Koezuka, L. Van Kaer, Nat. Med. 2001, 7, 1052-1056;
15. b) S. Sharif, G. A. Arreaza, P. Zucker, Q. S. Mi, J. Sondhi, O. V. Naidenko, M. Kronenberg, Y. Koezuka, T. L. Delovitch, J. M. Gombert, M. Leite-De-Moraes, C. Gouarin, R. Zhu, A. Hameg, T. Nakayama, M. Taniguchi, F. Lepault, A. Lehuen, J. F. Bach, A. Herbelin, Nat. Med. 2001, 7, 1057-1062.
16. K. Kakimi, L. G. Guidotti, Y. Koezuka, F. V. Chisari, J. Exp. Med. 2000, 192, 921-930.
17. K. Miyamoto, S. Miyake, T. Yamamura, Nature 2001, 413, 531-534.
18. a) L. Brossay, O. Naidenko, N. Burdin, J. Matsuda, T. Sakai, M. Kronenberg, J. Immunol. 1998, 161, 5124-5128;
19. b) K. Benlagha, A. Weiss, A. Beavis, L. Teyton, A. Bendelac, J. Exp. Med. 2000, 191, 1895.
20. a) D. B. Moody, G. S. Besra, I. A. Wilson, S. A. Porcelli, Immunol. Rev. 1999, 172, 285-296;
21. b) M. T. Wilson, A. K. Singh, L. Van Kaer, Trends Mol. Med. 2002, 8, 225-231.
22. a) For an overview of current research on glycosphingolipids in medicine, see: "Glycolipids in cell biology and medicine": Philos. Trans. Biol. Sci. 2003, 358, 845-983, organized and edited by R. A. Dwek, T. D. Butters, F. M. Platt, T. M. Cox;
23. b) for a review of marine glycolipids, see: E. Fattorusso, A. Mangoni, Fortschr. Chem. Org. Naturst. 1997, 72, 215-301.
24. M. Crul, R. A. Mathot, G. Giaccone, C. A. Punt, H. Rosing, M. X. Hillebrand, Y. Ando, N. Nishi, H. Tanaka, J. M. Schellens, J. H. Beijnen, Cancer Chemother. Pharmacol. 2002, 49, 287-293.
25. "Synthesis of C-Glycosides: Stable Mimics of O-Glycosidic Linkages": a) C. R. Bertozzi, M. D. Bednarski in Modern Methods in Carbohydrate Synthesis, Harwood Academic Publishers, Reading, 1996, pp. 316-351;
26. b) Y. Du, R. J. Linhardt, I. R. Vlahov, Tetrahedron 1998, 54, 9913-9959;
27. "C-Oligosaccharide Synthesis": T. Skrydstrup, B. Vauzailles, J.-M. Beau in Glycoscience: Chemistry and Chemical Biology, Vol. 3 (Eds.: B. Fraser Reid, K. Tatsuta, J. Thiem), Springer, Heidelberg, 2001, p. 2679.
28. For a C-trisaccharide with lectin-binding behavior similar to that of the parent O-trisaccharide, see: L. M. Mikkelsen, M. J. Hernaiz, M. Martin-Pastor, T. Skrydstrup, J. Jimenez-Barbero, J. Am. Chem. Soc. 2002, 124, 14940-14951.
29. a) For a C-glycoside with a tenfold loss of activity relative to phlorizin in an SGLT-inhibition assay, see: J. T. Link, B. K. Sorensen, Tetrahedron Lett. 2000, 41, 9213-9217;
30. b) for a C-glycoside with a 500-fold reduction in antileukemia activity relative to the parent daunomycin, see: E. M. Acton, K. J. Ryan, M. Tracy, S. K. Arora, Tetrahedron Lett. 1986, 27, 4245-4248.
31. C. R. Bertozzi, D. G. Cook, W. R. Kobertz, F. Gonzalez-Scarano, M. D. Bednarski, J. Am. Chem. Soc. 1992, 114, 10639-10641.
32. B. Waldscheck, M. Streiff, W. Notz, W. Kinzy, R. R. Schmidt, Angew. Chem. 2001, 113, 4120-4124; Angew. Chem. Int. Ed. 2001, 40, 4007-4011.
33. B. Waldscheck, M. Streiff, W. Notz, W. Kinzy, R. R. Schmidt, Angew. Chem. 2001, 113, 4120-4124; Angew. Chem. Int. Ed. 2001, 40, 4007-4011.
34. a) A. Dondoni, D. Perrone, E. Turturici, J. Org. Chem. 1999, 64, 5557-5564;
35. b) M. K. Gurjar, R. Reddy, Carbohydr. Lett. 1997, 2, 293-298.
36. For recent applications of the Ramberg-Bäcklund reaction to the synthesis of C-glycosides, see: a) D. E. Paterson, F. K. Griffin, M.-L. Alcaraz, R. J. K. Taylor, Eur. J. Org. Chem. 2002, 1323;
37. b) Y. Ohnishi, Y. Ichikawa, Bioorg. Med. Chem. Lett. 2002, 12, 997;
38. c) P. Pasetto, R. W. Franck, J. Org. Chem. 2003, 68, 8042-8060.
39. O. Shirota, K. Nakanishi, N. Berova, Tetrahedron 1999, 55, 13643-13658.
40. S. J. Spak, O. R. Martin, Tetrahedron 2000, 56, 217-224.
41. W. K. Park, S. S. J. Meunier, D. Zanini, R. Roy, Carbohydr. Lett. 1995, 1, 179-184.
42. R. Johansson, B. Samuelsson, J. Chem. Soc. Perkin Trans. 1 1984, 1, 2371-2374.
43. R. M. Burk, M. B. Roof, Tetrahedron Lett. 1993, 34, 395-398.
44. M. Yu, B. L. Pagenkopf, J. Org. Chem. 2002, 67, 4553-4558.
45. W. R. Roush, M. A. Adam, J. Org. Chem. 1985, 50, 3752-3757.
46. This synthesis of the C-glycoside 3 has been disclosed at ACS meetings and is the subject of a patent application: R. W. Franck, G. Yang, J. Schmeig, M. Tsuji, ACS Meeting, Boston, August 2002, ABS O-862; R. W. Franck, G. Yang, J. Schmeig, M. Tsuji, ACS Meeting, New Orleans, March 2003, ABS Carbo-26; "Synthetic C-glycolipid and its use for treating cancer, infectious diseases and autoimmune diseases": M. Tsuji, R. W. Franck, G. Yang, G. Chen, US Patent Provisional App. June, 2002, Full App. June 2003.
47. This synthesis of the C-glycoside 3 has been disclosed at ACS meetings and is the subject of a patent application: R. W. Franck, G. Yang, J. Schmeig, M. Tsuji, ACS Meeting, Boston, August 2002, ABS O-862; R. W. Franck, G. Yang, J. Schmeig, M. Tsuji, ACS Meeting, New Orleans, March 2003, ABS Carbo-26; "Synthetic C-glycolipid and its use for treating cancer, infectious diseases and autoimmune diseases": M. Tsuji, R. W. Franck, G. Yang, G. Chen, US Patent Provisional App. June, 2002, Full App. June 2003.
48. This synthesis of the C-glycoside 3 has been disclosed at ACS meetings and is the subject of a patent application: R. W. Franck, G. Yang, J. Schmeig, M. Tsuji, ACS Meeting, Boston, August 2002, ABS O-862; R. W. Franck, G. Yang, J. Schmeig, M. Tsuji, ACS Meeting, New Orleans, March 2003, ABS Carbo-26; "Synthetic C-glycolipid and its use for treating cancer, infectious diseases and autoimmune diseases": M. Tsuji, R. W. Franck, G. Yang, G. Chen, US Patent Provisional App. June, 2002, Full App. June 2003.
49. A. Jégou, C. Pacheco, A. Veyrières, Tetrahedron 1998, 54, 14 779-14 790.
50. G. Gonzalez-Aseguinolaza, C. de Oliveira, M. Tomaska, S. Hong, O. Bruan-Romero, T. Nakayama, M. Taniguchi, A. Bendela, L. Van Kaer, Y. Koezuka, M. Tsuji, Proc. Natl. Acad. Sci. USA 2000, 97, 8461-8466.
51. J. Schmieg, G. Yang, R. W. Franck, M. Tsuji, J. Exp. Med. 2003, 198, 1631-1641.