Pure and Applied Chemistry, 2012, Volume 84, No. 6, pp. 1341-1351, References

Pure Appl. Chem., 2012, Vol. 84, No. 6, pp. 1341-1351

http://dx.doi.org/10.1351/PAC-CON-11-08-22

Published online 2012-02-08

Synthesis and structure–activity studies of simplified analogues of aplysiatoxin with antiproliferative activity like bryostatin-1

Kazuhiro Irie^1,2*, Masayuki Kikumori¹, Hiroaki Kamachi¹, Keisuke Tanaka¹, Akira Murakami¹, Ryo C. Yanagita^3,1, Harukuni Tokuda⁴, Nobutaka Suzuki⁴, Hiroshi Nagai⁵, Kiyotake Suenaga⁶ and Yu Nakagawa^1,7

¹ Division of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan
² Research Unit for Physiological Chemistry, the Center for the Promotion of Interdisciplinary Education and Research, Kyoto University, Kyoto 606-8502, Japan
³ Department of Applied Biological Science, Faculty of Agriculture, Kagawa University, Kagawa 761-0195, Japan
⁴ Department of Complementary and Alternative Medicine, Clinical R&D, Graduate School of Medical Science, Kanazawa University, Kanazawa 920-8640, Japan
⁵ Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan
⁶ Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan
⁷ Synthetic Cellular Chemistry Laboratory, Advanced Science Institute, RIKEN, Saitama 351‑0198, Japan

References

1. Y. Nishizuka. FASEB J. 9, 484 (1995).
2. M. Castagna, Y. Takai, K. Kaibuchi, K. Sano, U. Kikkawa, Y. Nishizuka. J. Biol. Chem. 257, 7847 (1982).
3. H. Fujiki, T. Sugimura. Adv. Cancer Res. 49, 223 (1987). (http://dx.doi.org/10.1016/S0065-230X(08)60799-X)
4. G. R. Pettit, C. L. Herald, D. L. Doubek, D. L. Herald, E. Arnold, J. Clardy. J. Am. Chem. Soc. 104, 6846 (1982). (http://dx.doi.org/10.1021/ja00388a092)
5. H. Hennings, P. M. Blumberg, G. R. Pettit, C. L. Herald, R. Shores, S. H. Yuspa. Carcinogenesis 8, 1343 (1987). (http://dx.doi.org/10.1093/carcin/8.9.1343)
6. Z. Szállási, M. F. Denning, C. B. Smith, A. A. Dlugosz, S. H. Yuspa, G. R. Pettit, P. M. Blumberg. Mol. Pharmacol. 46, 840 (1994).
7. M. Fährmann. Curr. Med. Chem. 15, 1175 (2008). (http://dx.doi.org/10.2174/092986708784310413)
8. H. J. Mackay, C. J. Twelves. Nat. Rev. Cancer 7, 554 (2007). (http://dx.doi.org/10.1038/nrc2168)
9. G. K. Schwartz, M. A. Shah. J. Clin. Oncol. 23, 9408 (2005). (http://dx.doi.org/10.1200/JCO.2005.01.5594)
10. P. M. Barr, H. M. Lazarus, B. W. Cooper, M. D. Schluchter, A. Panneerselvam, J. W. Jacobberger, J. W. Hsu, N. Janakiraman, A. Simic, A. Dowlati, S. C. Remick. Am. J. Hematol. 84, 484 (2009). (http://dx.doi.org/10.1002/ajh.21449)
11. M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune. J. Am. Chem. Soc. 112, 7407 (1990). (http://dx.doi.org/10.1021/ja00176a058)
12. D. A. Evans, P. H. Carter, E. M. Carreira, A. B. Charette, J. A. Prunet, M. Lautens. J. Am. Chem. Soc. 121, 7540 (1999). (http://dx.doi.org/10.1021/ja990860j)
13. K. Ohmori, Y. Ogawa, T. Obitsu, Y. Ishikawa, S. Nishiyama, S. Yamamura. Angew. Chem., Int. Ed. 39, 2290 (2000). (http://dx.doi.org/10.1002/1521-3773(20000703)39:13<2290::AID-ANIE2290>3.0.CO;2-6)
14. 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. S. Lippa, P. G. Nell, T. M. Turner. J. Am. Chem. Soc. 124, 13648 (2002). (http://dx.doi.org/10.1021/ja027509+)
15. P. A. Wender, J. L. Baryza, S. E. Brenner, B. A. Dechristopher, B. A. Loy, A. J. Schrier, V. A. Verma. Proc. Natl. Acad. Sci. USA 108, 6721 (2011). (http://dx.doi.org/10.1073/pnas.1015270108)
16. G. E. Keck, M. B. Kraft, A. P. Truong, W. Li, C. C. Sanchez, N. Kedei, N. E. Lewin, P. M. Blumberg. J. Am. Chem. Soc. 130, 6660 (2008). (http://dx.doi.org/10.1021/ja8022169)
17. G. E. Keck, W. Li, M. B. Kraft, N. Kedei, N. E. Lewin, P. M. Blumberg. Org. Lett. 11, 2277 (2009). (http://dx.doi.org/10.1021/ol900585t)
18. B. M. Trost, G. Dong. Nature 456, 485 (2008). (http://dx.doi.org/10.1038/nature07543)
19. B. M. Trost, G. J. Dong. J. Am. Chem. Soc. 132, 16403 (2010). (http://dx.doi.org/10.1021/ja105129p)
20. P. A. Wender, A. J. Schrier. J. Am. Chem. Soc. 133, 9228 (2011). (http://dx.doi.org/10.1021/ja203034k)
21. G. E. Keck, Y. B. Poudel, T. J. Cummins, A. Rudra, J. A. Covel. J. Am. Chem. Soc. 133, 744 (2011). (http://dx.doi.org/10.1021/ja110198y)
22. S. Manaviazar, M. Frigerio, G. S. Bhatia, M. G. Hummersone, A. E. Aliev, K. J. Hale. Org. Lett. 8, 4477 (2006). (http://dx.doi.org/10.1021/ol061626i)
23. Y. Lu, S. K. Woo, M. J. Krische. J. Am. Chem. Soc. 133, 13876 (2011). (http://dx.doi.org/10.1021/ja205673e)
24. Y. Nakagawa, R. C. Yanagita, N. Hamada, A. Murakami, H. Takahashi, N. Saito, H. Nagai, K. Irie. J. Am. Chem. Soc. 131, 7573 (2009). (http://dx.doi.org/10.1021/ja808447r)
25. Z. Lu, A. Hornia, Y.-W. Jiang, Q. Zang, S. Ohno, D. A. Foster. Mol. Cell Biol. 17, 3418 (1997).
26. P. J. Reddig, N. E. Dreckschmidt, H. Ahrens, R. Simsiman, C. Tseng, J. Zou, T. D. Oberley, A. K. Verma. Cancer Res. 59, 5710 (1999).
27. Y. Ono, T. Fujii, K. Igarashi, T. Kuno, C. Tanaka, U. Kikkawa, Y. Nishizuka. Proc. Natl. Acad. Sci. USA 86, 4868 (1989). (http://dx.doi.org/10.1073/pnas.86.13.4868)
28. Z. Szállási, K. Bögi, S. Gohari, T. Biro, P. Ács, P. M. Blumberg. J. Biol. Chem. 271, 18299 (1996).
29. K. Bögi, P. S. Lorenzo, Z. Szállási, P. Ács, G. S. Wagner, P. M. Blumberg. Cancer Res. 58, 1423 (1998).
30. K. Irie, Y. Nakagawa, H. Ohigashi. Curr. Pharm. Design 10, 1371 (2004). (http://dx.doi.org/10.2174/1381612043384907)
31. Q. J. Wang, D. Bhattacharyya, S. Garfield, K. Nacro, V. E. Marquez, P. M. Blumberg. J. Biol. Chem. 274, 37233 (1999). (http://dx.doi.org/10.1074/jbc.274.52.37233)
32. Q. J. Wang, T.-W. Fang, D. Fenick, S. Garfield, B. Bienfait, V. E. Marquez, P. M. Blumberg. J. Biol. Chem. 275, 12136 (2000). (http://dx.doi.org/10.1074/jbc.275.16.12136)
33. P. A. Wender, K. Irie, B. L. Miller. Proc. Natl. Acad. Sci. USA 92, 239 (1995). (http://dx.doi.org/10.1073/pnas.92.1.239)
34. K. Irie, K. Oie, A. Nakahara, Y. Yanai, H. Ohigashi, P. A. Wender, H. Fukuda, H. Konishi, U. Kikkawa. J. Am. Chem. Soc. 120, 9159 (1998). (http://dx.doi.org/10.1021/ja981087f)
35. M. Shindo, K. Irie, A. Nakahara, H. Ohigashi, H. Konishi, U. Kikkawa, H. Fukuda, P. A. Wender. Bioorg. Med. Chem. 9, 2073 (2001). (http://dx.doi.org/10.1016/S0968-0896(01)00100-6)
36. K. Irie, R. C. Yanagita, Y. Nakagawa. Med. Res. Rev. In press.
37. Y. Kato, P. J. Scheuer. J. Am. Chem. Soc. 96, 2245 (1974). (http://dx.doi.org/10.1021/ja00814a041)
38. Y. Kato. J. Syn. Org. Chem. Japan 68, 757 (2010). (http://dx.doi.org/10.5059/yukigoseikyokaishi.68.757)
39. M. Shimomura, M. G. Mullinix, T. Kakunaga, H. Fujiki, T. Sugimura. Science 222, 1242 (1983). (http://dx.doi.org/10.1126/science.6316505)
40. M. Suganuma, H. Fujiki, T. Tahira, C. Cheuk, R. E. Moore, T. Sugimura. Carcinogenesis 5, 315 (1984). (http://dx.doi.org/10.1093/carcin/5.3.315)
41. H. Nakamura, Y. Kishi, M. A. Pajares, R. R. Rando. Proc. Natl. Acad. Sci. USA 86, 9672 (1989). (http://dx.doi.org/10.1073/pnas.86.24.9672)
42. R. R. Rando, Y. Kishi. Biochemistry 31, 2211 (1992). (http://dx.doi.org/10.1021/bi00123a001)
43. R. C. Yanagita, H. Kamachi, K. Tanaka, A. Murakami, Y. Nakagawa, H. Tokuda, H. Nagai, K. Irie. Bioorg. Med. Chem. Lett. 20, 6064 (2010). (http://dx.doi.org/10.1016/j.bmcl.2010.08.051)
44. P. Park, C. A. Broka, B. F. Johnson, Y. Kishi. J. Am. Chem. Soc. 109, 6205 (1987). (http://dx.doi.org/10.1021/ja00254a062)
45. H. Okamura, S. Kuroda, S. Ikegami, Y. Ito, T. Katsuki, M. Yamaguchi. Tetrahedron Lett. 32, 5141 (1991). (http://dx.doi.org/10.1016/S0040-4039(00)93449-X)
46. H. Toshima, T. Suzuki, S. Nishiyama, S. Yamamura. Tetrahedron Lett. 30, 6725 (1989). (http://dx.doi.org/10.1016/S0040-4039(00)70661-7)
47. G. E. Keck, D. Krishnamurthy. Org. Synth. 75, 12 (1998).
48. J. J.-W. Duan, A. B. Smith III. J. Org. Chem. 58, 3703 (1993). (http://dx.doi.org/10.1021/jo00066a024)
49. M. Ide, M. Nakata. Bull. Chem. Soc. Jpn. 72, 2491 (1999). (http://dx.doi.org/10.1246/bcsj.72.2491)
50. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, Y. Yamaguchi. Bull. Chem. Soc. Jpn. 52, 1989 (1979). (http://dx.doi.org/10.1246/bcsj.52.1989)
51. H. zur Hausen, G. W. Bornkamm, R. Schmidt, E. Hecker. Proc. Natl. Acad. Sci. USA 76, 782 (1979). (http://dx.doi.org/10.1073/pnas.76.2.782)
52. Y. Ito, S. Yanase, J. Fujita, T. Harayama, M. Takashima, H. Imanaka. Cancer Lett. 13, 29 (1981). (http://dx.doi.org/10.1016/0304-3835(81)90083-5)
53. T. Yamori. Cancer Chemother. Pharmacol. 52, 574 (2003). (http://dx.doi.org/10.1007/s00280-003-0649-1)
54. Y. Nakagawa, M. Kikumori, R. C. Yanagita, A. Murakami, H. Tokuda, H. Nagai, K. Irie. Biosci. Biotechnol. Biochem. 75, 1167 (2011). (http://dx.doi.org/10.1271/bbb.110130)
55. M. Hunn, A. F. G. Quest. FEBS Lett. 400, 226 (1997). (http://dx.doi.org/10.1016/S0014-5793(96)01395-6)
56. SciBX 2, 11 (2009).
57. N. Kedei, E. Lubart, N. E. Lewin, A. Telek, L. Lim, P. Mannan, S. H. Garfield, M. B. Kraft, G. E. Keck, S. Kousheva, R. Jelinek, P. M. Blumberg. ChemBioChem 12, 1242 (2011). (http://dx.doi.org/10.1002/cbic.201100064)

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Synthesis and structure–activity studies of simplified analogues of aplysiatoxin with antiproliferative activity like bryostatin-1

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Synthesis and structure–activity studies of simplified analogues of aplysiatoxin with antiproliferative activity like bryostatin-1

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