Penaramides, which inhibit binding of ω-conotoxin GVIA to N-type Ca2+ channels, from the marine sponge Penares aff. Incruston s

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 225-228

  Ushio Sata, Noriko ^a   Matsunaga, Shigeki ^a   Fusetani, Nobuhiro ^a   Honda, Kazuo ^b   Yasumuro, Kenichi ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PENARES; ANIMALIA;

CALCIUM CHANNEL; OMEGA CONOTOXIN GVIA; PENARAMIDE; PENARAMIDE A; POLYAMINE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BRAIN; CONTROLLED STUDY; DRUG BINDING; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NEUROTOXICITY; NONHUMAN; RAT; SPONGE;

EID: 0030053379     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02134-5     Document Type: Article

References (18)

1. Bioactive marine metabolites. 73. Part 72: Li, H.; Matsunaga, S.; Fusetani, N., J. Nat. Prod., in press.
2. (a) Bean, B. P. Ann. Rev. Physiol. 1989, 51, 367-384.
3. (b) Llinás, R.; Sugimori, M.; Lin, J. W.; Chersksey, B. Proc. Natl. Acad. Sci. USA, 1989, 86, 1689-1693.
4. (a) MaCleskey, E. W.; Fox, A. P.; Feldman, D. H.; Cruz, L. J.; Olivera, B. M.; Tsien, R. W.; Yoshikami, D. Proc. Natl. Acad. Sci. USA, 1987, 84, 4327-4331.
5. (b) Gray, W. R.; Olivera, B. M.; Cruz, L. Ann. Rev. Biochem. 1988, 57, 665-700.
6. (a) Barhanin, J.; Schmid, A.; Lazdunski, M. Biochem. Biophys. Res. Commun. 1988, 150, 1051-1062.
7. (b) Feigenbaum, P.; Garcia, M. L.; Kaczorowski, G. J. Biochem. Biophys. Res. Commun. 1988, 154, 298-305.
8. Further purification was hampered due to the presence of numerous closely related compounds, leading to a broad peak in HPLC.
9. 11 fatty acids were identified on the basis of fragment ions in the EIMS: n-undecanoic acid [m/z (rel intensity): 200 (26%), 157 (17), 143 (15), 87 (69)], 9-methyldecanoic acid [200 (12), 157 (31), 143 (22), 87 (62)], 8-methyldecanoic acid [200 (29), 143 (63), 87 (64)], 4-methyldecanoic acid [200 (9), 143 (26), 87 (100)], and 3-methyldecanoic acid [200 (10), 101 (48)].
10. 2 and C3/C5 led to the connection of C3 and C5 through the ammonium nitrogen.
11. +. Found: 773.7121.
12. Gross, M. L. Acc. Chem. Res. 1994, 27, 361 -369.
13. (a) Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1988, 53, 3108-3111.
14. (b) Israel, M.; Rosenfield, J. S.; Modest, E. J.J. Med. Chem. 1964, 1, 710-717.
15. Yamamoto, H.; Maruoka, K. J. Am. Chem. Soc. 1981, 103, 6133-6136.
16. Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 154-158.
17. Chen, F. C. M.; Benoiton, N. L. Can. J. Chem. 1976, 54, 3310-3311.
18. +. Found: 773.7103.