Artificial ladder-shaped polyethers that inhibit maitotoxin-induced Ca 2+ influx in rat glioma C6 cells

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 11, 2012, Pages 3619-3622

  Oishi, Tohru ^a   Konoki, Keiichi ^b   Tamate, Rie ^c   Torikai, Kohei ^a   Hasegawa, Futoshi ^c   Matsumori, Nobuaki ^c   Murata, Michio ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

Artificial ladder shaped polyether; Calcium ion; Inhibitor; Maitotoxin; Natural product

Indexed keywords

ALP7B; BREVETOXIN; BREVETOXIN A; BREVETOXIN B; CALCIUM ION; GAMBIERIC ACID A; GAMBIEROL; MAITOTOXIN; MEMBRANE PROTEIN; POLYETHER; POLYETHER DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; GLIOMA CELL; NONHUMAN; PROTEIN INTERACTION; RAT;

ANIMALS; CALCIUM; DINOFLAGELLIDA; ETHERS, CYCLIC; GLIOMA; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; ION TRANSPORT; MARINE TOXINS; MEMBRANE PROTEINS; OXOCINS; RATS; TUMOR CELLS, CULTURED;

DINOPHYCEAE; GAMBIERDISCUS TOXICUS; MAMMALIA; RATTUS;

EID: 84861185478     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.04.053     Document Type: Article

References (41)

1. T. Yasumoto, R. Bagins, and J.P. Venoux Bull. Jpn. Soc. Sci. Fish. 42 1976 359
2. M. Murata, T. Iwashita, A. Yokoyama, M. Sasaki, and T. Yasumoto J. Am. Chem. Soc. 114 1992 6594
3. M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama, and T. Yasumoto J. Am. Chem. Soc. 115 1993 2060
4. M. Murata, H. Naoki, S. Matsunaga, M. Satake, and T. Yasumoto J. Am. Chem. Soc. 116 1994 7098
5. M. Satake, S. Ishida, T. Yasumoto, M. Murata, H. Utsumi, and T. Hinomoto J. Am. Chem. Soc. 117 1995 7019
6. M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, and T. Yasumoto Angew. Chem., Int. Ed. 35 1996 1672
7. T. Nonomura, M. Sasaki, N. Matsumori, M. Murata, K. Tachibana, and T. Yasumoto Angew. Chem., Int. Ed. 35 1996 1675
8. W. Zheng, J.A. DeMattei, J.-P. Wu, J.J.-W. Duan, L.R. Cook, H. Oinuma, and Y. Kishi J. Am. Chem. Soc. 118 1996 7946
9. L.R. Cook, H. Oinuma, M.A. Semones, and Y. Kishi J. Am. Chem. Soc. 119 1997 7928
10. Y. Kishi Pure Appl. Chem. 70 1998 339
11. K.C. Nicolaou, K.P. Cole, M.O. Frederick, R.J. Aversa, and R.M. Denton Angew. Chem., Int. Ed. 46 2007 8875
12. K.C. Nicolaou, and M.O. Frederick Angew. Chem., Int. Ed. 46 2007 5278
13. K.C. Nicolaou, M.H.D. Postema, E.W. Yue, and A. Nadin J. Am. Chem. Soc. 118 1996 10335
14. M. Satoh, H. Koshino, and T. Nakata Org. Lett. 10 2008 1683
15. M. Morita, T. Haketa, H. Koshino, and T. Nakata Org. Lett. 10 2008 1679
16. M. Morita, S. Ishiyama, H. Koshino, and T. Nakata Org. Lett. 10 2008 1675
17. Y. Sakamoto, G. Matsuo, H. Matsukura, and T. Nakata Org. Lett. 3 2001 2749
18. M. Murata, N. Matsumori, K. Konoki, and T. Oishi Bull. Chem. Soc. Jpn. 81 2008 307
19. T. Igarashi, S. Aritake, and T. Yasumoto Nat. Toxins 7 1999 71
20. K. Konoki, M. Hashimoto, T. Nonomura, M. Sasaki, M. Murata, and K. Tachibana J. Neurochem. 70 1998 409
21. For a review, see: F. Gusovsky, and J.W. Daly Biochem. Pharmacol. 39 1990 1633
22. M. Takahashi, Y. Ohizumi, and Y. Yasumoto J. Biol. Chem. 257 1982 7287
23. P. Dietl, and H. Voelkl Mol. Pharmacol. 45 1994 300
24. J.W. Daly, J. Lueders, W.L. Padgett, Y. Shin, and F. Gusovsky Biochem. Pharmacol. 50 1995 1187
25. A. Bielfeld-Ackermann, C. Range, and C. Korbmacher Pfluegers Arch. 436 1998 329
26. W.G. Sinkins, M. Estacion, V. Prasad, M. Goel, G.E. Shull, D.L. Kunze, and W.P. Schilling Am. J. Phisiol. Cell Phisiol. 297 2009 C1533
27. K. Konoki, M. Hashimoto, K. Honda, K. Tachibana, R. Tamate, F. Hasegawa, T. Oishi, and M. Murata Heterocycles 79 2009 1007
28. Y.-Y. Lin, M. Risk, S.M. Ray, D.V. Engen, J. Clardy, J. Golik, J.C. James, and K. Nakanishi J. Am. Chem. Soc. 103 1981 6773
29. Y. Shimizu, H.-N. Chou, H. Bando, G. Van Duyne, and J.C. Clardy J. Am. Chem. Soc. 108 1986 514
30. J. Pawlak, M.S. Tempesta, J. Golik, M.G. Zagorski, M.S. Lee, K. Nakanishi, T. Iwashita, M.L. Gross, and K.B. Tomer J. Am. Chem. Soc. 109 1987 1144
31. V.L. Trainer, D.G. Baden, and W.A. Catterall J. Biol. Chem. 269 1994 19904
32. M. Inoue, M. Hirama, M. Satake, K. Sugiyama, and T. Yasumoto Toxicon 41 2003 469
33. H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto, and H. Hirota J. Am. Chem. Soc. 114 1992 1102
34. H. Nagai, M. Murata, K. Torigoe, M. Satake, and T. Yasumoto J. Org. Chem. 57 1992 5448
35. A. Morohashi, M. Satake, H. Nagai, Y. Oshima, and T. Yasumoto Tetrahedron 56 2000 8995
36. M. Satake, M. Murata, and T. Yasumoto J. Am. Chem. Soc. 115 1993 361
37. A. Morohashi, M. Satake, and T. Yasumoto Tetrahedron Lett. 40 1999 97
38. T. Oishi, F. Hasegawa, K. Torikai, K. Konoki, N. Matsumori, and M. Murata Org. Lett. 10 2008 3599
39. K. Torikai, H. Yari, M. Mori, S. Ujihara, N. Matsumori, M. Murata, and T. Oishi Bioorg. Med. Chem. Lett. 16 2006 6355
40. K. Torikai, H. Yari, M. Murata, and T. Oishi Heterocycles 70 2006 161
41. K. Torikai, T. Oishi, S. Ujihara, N. Matsumori, K. Konoki, M. Murata, and S. Aimoto J. Am. Chem. Soc. 130 2008 10217