The twisted side chain of antillatoxin is important for potent toxicity: Total synthesis and biological evaluation of antillatoxin and analogues

Angewandte Chemie - International Edition

Volumn 49, Issue 2, 2010, Pages 329-332

  Okura, Ken ^a   Matsuoka, Shigeru ^a   Goto, Ryosuke ^a   Inoue, Masayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Biological activity; Conformation analysis; Natural products; Structure activity relationships; Total synthesis

Indexed keywords

BIOLOGICAL ACTIVITIES; BIOLOGICAL ACTIVITY CONFORMATION ANALYSIS; BIOLOGICAL EVALUATION; CHEMICAL EQUATIONS; CONFORMATIONAL ANALYSIS; CYCLIC PEPTIDES; NATURAL PRODUCTS; SIDE CHAINS; SIDE-CHAIN; SIDE-CHAIN ANALOGUES; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS;

BIOACTIVITY; PEPTIDES; SYNTHESIS (CHEMICAL);

CONFORMATIONS;

ANTILLATOXIN; CYCLOPEPTIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LIPOPEPTIDE; NEUROTOXIN; SODIUM CHANNEL;

ANIMAL; ARTICLE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYANOBACTERIUM; DRUG POTENTIATION; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; CYANOBACTERIA; INDICATORS AND REAGENTS; LIPOPEPTIDES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEUROTOXINS; PEPTIDES, CYCLIC; SODIUM CHANNELS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 73349100353     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200905892     Document Type: Article

References (29)

1. W. A. Catterall, Neuron 2000, 26, 13-25.
2. a) J. J. Clare, S. N. Tate, M. Nobbs, M. A. Romanos, Drug Discovery Today 2000, 5, 506-520;
3. b) A. Al-Sabi, J. McArthur, V. Ostroumov, R. J. French, Mar. Drugs 2006, 4, 157-192.
4. a) S.-Y. Wang, G. K. Wang, Cell. Signalling 2003, 15, 151-159;
5. b) W. A. Catterall, S. Cestele, V. Yarov-Yarovoy, F. H. Yu, K. Konoki, T. Scheuer, Toxicon 2007, 49, 124-141.
6. J. Orjala, D. G. Nagle, V. Hsu, W. H. Gerwick, J. Am. Chem. Soc. 1995, 117, 8281-8282.
7. The first proposed NMR-based structure (4S,5R)-1 was revised to be (4R,5R)-1 by Shioiri and co-workers through total syntheses of the isomers: a) F. Yokokawa, H. Fujiwara, T. Shioiri, Tetrahedron Lett. 1999, 40, 1915 -1916;
8. Total synthesis of (4S,5S)-, (4S,5R)-, (4R,5S)- and (4R,5R)-1: b) F. Yokokawa, H. Fujiwara, T. Shioiri, Tetrahedron 2000, 56, 1759-1775;
9. Total synthesis of (4S,5R)-1: c) F. Yokokawa, T. Shioiri, J. Org. Chem. 1998, 63, 8638-8639;
10. d) J. D. White, R. Hanselmann, D. J. Wardrop, J. Am. Chem. Soc. 1999, 121, 1106-1107;
11. Total synthesis of (4S,5S)- and (4R,5R)-1: e) K.-C. Lee, T.-P. Loh, Chem. Commun. 2006, 4209-4211.
12. Gerwick, Murray, and co-workers reported the extensive biological studies of antillatoxin as well as the SAR studies of (4S,5S)-, (4S,5R)-, (4R,5S)- and (4R,5R)-1; a) F. W. Berman, W. H. Gerwick, T. F. Murray, Toxicon 1999, 37, 1645-1648;
13. b) W. I. Li, F. W. Berman, T. Okino, F. Yokokawa, T. Shioiri, W. H. Gerwick, T. F. Murray, Proc. Natl. Acad. Sci. USA 2001, 95, 7599-7604;
14. c) W. I. Li, B. L. Marquez, T. Okino, F. Yokokawa, T. Shioiri, W. H. Gerwick, T. F. Murray, J. Nat. Prod. 2004, 67, 559-568;
15. d) Z. Cao, J. George, W. H. Gerwick, D. G. Baden, J. D. Rainier, T. F. Murray, J. Pharmacol. Exp. Ther. 2008, 326, 604-613.
16. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
17. a) H. Ishitani, Y. Yamashita, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 5403-5404;
18. b) S. Kobayashi, K. Mori, T. Wakabayashi, S. Yasuda, K. Hanada, J. Org. Chem. 2001, 66, 5580-5584.
19. R. Baker, J. L. Castro, J. Chem. Soc. Perkin Trans. 1 1990, 47-65.
20. A. Erkkilä, P. M. Pihko, J. Org. Chem. 2006, 71, 2538-2541.
21. K. Ogura, N. Yahata, M. Minoguchi, K. Ohtsuki, K. Takahashi, H. Iida, J. Org. Chem. 1986, 51, 508-512.
22. M. Hirama, H. Hioki, S. Itô, Tetrahedron Lett. 1988, 29, 3125-3128.
23. 3) resulted in lower yields.
24. C. E. Tucker, J. Davidson, P. Knochel, J. Org. Chem. 1992, 57, 3482-3485.
25. C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014-11015.
26. See the Supporting Information for details.
27. T. A. Halgren, J. Comput. Chem. 1999, 20, 730-748, and references therein.
28. H. Guo, M. Karplus, J. Mol. Struct. 1992, 260, 347-393.
29. Only one of the two twisted conformations could be important for the biological activity, and its determination necessitates additional SAR studies.