Role of the phenolic hydroxyl group in the biological activities of simplified analogue of aplysiatoxin with antiproliferative activity

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 20, 2010, Pages 6064-6066

  Yanagita, Ryo C ^a   Kamachi, Hiroaki ^a   Tanaka, Keisuke ^a   Murakami, Akira ^a   Nakagawa, Yu ^b   Tokuda, Harukuni ^c   Nagai, Hiroshi ^d   Irie, Kazuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c KANAZAWA UNIVERSITY   (Japan)

^d TOKYO UNIVERSITY OF MARINE SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Antiproliferative; Aplysiatoxin; Bryostatin; Epstein Barr virus; Phorbol ester; Protein kinase C; Tumor promoter

Indexed keywords

ALKALOID DERIVATIVE; APLYSIATOXIN; PHENOL DERIVATIVE; PROTEIN KINASE C; PROTEIN KINASE C DELTA; TELEOCIDIN B4; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CELL PROLIFERATION; DRUG ACTIVITY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IN VITRO STUDY; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION; TUMOR;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; HYDROXYL RADICAL; LYNGBYA TOXINS; NEOPLASMS; PROTEIN KINASE C;

HUMAN HERPESVIRUS 4;

EID: 77956937206     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.051     Document Type: Article

References (29)

1. Y. Nishizuka Nature 308 1984 693
2. Y. Nishizuka FASEB J. 9 1995 484
3. A.C. Newton J. Biol. Chem. 270 1995 28495
4. E. Hecker Naturwissenschaften 54 1967 282
5. H. Nakata, H. Harada, and Y. Hirata Tetrahedron Lett. 23 1966 2515
6. H. Fujiki, and T. Sugimura Adv. Cancer Res. 49 1987 223
7. Y. Kato, and P.J. Scheuer J. Am. Chem. Soc. 96 1974 2245
8. G.R. Pettit, C.L. Herald, D.L. Doubek, D.L. Herald, E. Arnold, and J. Clardy J. Am. Chem. Soc. 104 1982 6846
9. H. Hennings, P.M. Blumberg, G.R. Pettit, C.L. Herald, R. Shores, and S.H. Yuspa Carcinogenesis 8 1987 1343
10. M. Gschwendt, G. Fürstenberger, S. Rose-John, M. Rogers, W. Kittstein, G.R. Pettit, C.L. Herald, and F. Marks Carcinogenesis 9 1988 555
11. K.J. Hale, M.G. Hummersone, S. Manaviazar, and M. Frigerio Nat. Prod. Rep. 19 2002 413
12. M.K. Sun, and D.L. Alkon CNS Drug Rev. 12 2006 1
13. Z. Szallasi, L. Krsmanovic, and P.M. Blumberg Cancer Res. 53 1993 2507
14. Z. Szallasi, and P.M. Blumberg Cancer Res. 51 1991 5355
15. B. Czerniecki, S.C. Gad, C. Reilly, A.C. Smith, and G. Witz Carcinogenesis 7 1986 1637
16. R.E. Moore H. Fujiki, E. Hecker, R.E. Moore, T. Sugimura, I.B. Weinstein, Cellular Interactions by Environmental Tumor Promoters 1984 Japan Scientific Society Press/VNU Science Press Tokyo/Utrecht 49 57
17. H. Fujiki, and T. Sugimura T.J. Slaga, R. Montesano, Cancer Survey Vol. 2 1984 Oxford University Press London 539 556
18. Y. Nakagawa, R.C. Yanagita, N. Hamada, A. Murakami, H. Takahashi, N. Saito, H. Nagai, and K. Irie J. Am. Chem. Soc. 131 2009 7573
19. 3, 22.7 °C).
20. K. Irie, K. Oie, A. Nakahara, Y. Yanai, H. Ohigashi, P.A. Wender, H. Fukuda, H. Konishi, and U. Kikkawa J. Am. Chem. Soc. 120 1998 9159
21. H. Nakamura, Y. Kishi, M.A. Pajares, and R.R. Rando Proc. Natl. Acad. Sci. U.S.A. 86 1989 9672
22. T. Yamori Cancer Chemother. Pharmacol. 52 2003 S74
23. P.A. Wender, J.L. Baryza, C.E. Bennett, F.C. Bi, S.E. Brenner, M.O. Clarke, J.C. Horan, C. Kan, E. Lacôte, B. Lippa, P.G. Nell, and T.M. Turner J. Am. Chem. Soc. 124 2002 13648
24. Y. Ito, S. Yanase, J. Fujita, T. Harayama, M. Takashima, and H. Imanaka Cancer Lett. 13 1981 29
25. K. Irie, A. Nakahara, Y. Ikawa, M. Tanaka, Y. Nakagawa, Y. Nakamura, H. Ohigashi, and P.A. Wender Biosci. Biotechnol. Biochem. 64 2000 2429
26. K. Irie, T. Isaka, Y. Iwata, Y. Yanai, Y. Nakamura, F. Koizumi, H. Ohigashi, P.A. Wender, Y. Satomi, and H. Nishino J. Am. Chem. Soc. 118 1996 10733
27. N. Setterblad, I. Onyango, U. Pihlgren, L. Rask, and G. Andersson J. Immunol. 161 1998 4819
28. K. Kamimura, H. Hojo, and M. Abe Pathol. Int. 54 2004 224
29. M. Shindo, K. Irie, A. Nakahara, H. Ohigashi, H. Konishi, U. Kikkawa, H. Fukuda, and P.A. Wender Bioorg. Med. Chem. 9 2001 2073