Syntheses of fluorescence-labeled sphingosine 1-phosphate methylene and sulfur analogues as possible visible ligands to the receptor

Chemistry Letters

Volumn 37, Issue 2, 2008, Pages 188-189

  Yamamoto, Tetsuya ^a   Hasegawa, Hiroko ^a   Hakogi, Toshikazu ^a   Katsumura, Shigeo ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 40449111334     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.188     Document Type: Article

References (23)

1. For recent reviews on signal transduction mediated by sphingolipids, see: a) J. Liao, J. Tao, G. Lin, D. Liu, Tetrahedron 2005, 61, 4715.
2. b) A. Delgado, J. Casas, A. Llebaria, J. L. Abad, ChemMedChem 2007, 2, 580.
3. c) T. Baumruker, A. Billich, Curr. Immun. Rev. 2006, 2, 101, and references cited therein.
4. H. Zhang, N. N. Desai, A. Olivera, T. Seki, G. Brooker, S. Spiegel, J. Cell Biol. 1991, 114, 155.
5. M. J. Lee, S. Thangada, K. P. Claffey, N. Ancellin, C. H. Liu, M. Kluk, M. Volpi, R. I. Sha'afi, T. Hla, Cell 1999, 99, 301.
6. Y. Yatomi, F. Ruan, S. Hakomori, Y. Igarashi, Blood 1995, 86, 193.
7. We reported the syntheses of the following various sphingomyelin analogues: a) Carbon analogues: T. Hakogi, Y. Monden, M. Taichi, S. Iwama, S. Fujii, K. Ikeda, S. Katsumura, J. Org. Chem. 2002, 67, 4839.
8. b) Nitrogen analogue: T. Hakogi, M. Taichi, S. Katsumura, Org. Lett. 2003, 5, 2801.
9. c) Sulfur analogue: T. Hakogi, S. Fujii, M. Morita, K. Ikeda, S. Katsumura, Bioorg. Med. Chem. Lett. 2005, 15, 2141.
10. d) Difluoromethylene analogue: T. Hakogi, T. Yamamoto, S. Fujii, K. Ikeda, S. Katsumura, Tetrahedron Lett. 2006, 47, 2627.
11. T. Hakogi, T. Shigenari, S. Katsumura, T. Sano, T. Kohno, Y. Igarashi, Bioorg. Med. Chem. Lett. 2003, 13, 661.
12. a) H. Hasegawa, T. Yamamoto, S. Hatano, T. Hakogi, S. Katsumura, Chem. Lett. 2004, 33, 1592.
13. b) T. Yamamoto, H. Hasegawa, T. Hakogi, S. Katsumura, Org. Lett. 2006, 8, 5569.
14. a) R. H. Grubbs, Handbook of Metathesis, Wiley-VCH, Germany, 2003.
15. b) S. Connon, S. Blechert, Angew. Chem., Int. Ed. 2003, 42, 1900, and references cited therein.
16. For other reports on functionalized sphingolipids: a) P. Nussbaumer, P. Ettmayer, C. Peters, D. Rosenbeiger, K. Hoegenauer, Chem. Commun. 2005, 5086.
17. b) C. Peters, A. Billich, M. Ghobrial, K. Hoegenauer, T. Ullrich, P. Nussbaumer, J. Org. Chem. 2007, 72, 1842, and references cited therein.
18. D. B. Berkowitz, G. Maiti, B. D. Charette, C. D. Dreis, R. G. MacDonald, Org. Lett. 2004, 6, 4921.
19. The alkylation of the triflate 9 with a dimethyl phosphonate anion resulted in a low yield when 9 was added to the lithium anion of a dimethyl methylphosphonate solution at -78 °C in Ref. 10.
20. C. E. McKenna, J. Schmidhauser, J. Chem. Soc., Chem. Commun. 1979, 739.
21. C-P = 13.9Hz), 23.2.
22. C-P = 11.4Hz), 28.0.
23. In the preliminary qualitative tests, the synthesized 3 and 4 showed a moderate ability as ligands toward the sphingosine 1-phosphate receptor, S1P1, based on the results that the synthesized 3 and 4 reasonably expelled the radiolabeled S1P similarly to NBD-S1P in S1P1-expressing Chinese hamster ovary cells. We are grateful to Prof. Igarashi and co-workers of Hokkaido University for their biological testing.