Synthesis and tumor-promoting activities of 12-Epi-phorbol-12,13-dibutyrate

Bioscience, Biotechnology and Biochemistry

Volumn 64, Issue 11, 2000, Pages 2429-2436

  Irie, Kazuhiro ^a   Nakahara, Akifumi ^a   Ikawa, Yasuyuki ^a   Tanaka, Minoru ^a   Nakagavva, Yu ^a   Nakamura, Yoshimasa ^a   Ohigashi, Hajime ^a   Wender, Paul A ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b STANFORD UNIVERSITY   (United States)

Author keywords

12 epi phorbol 12,13 dibutyrate; Epstein Barr virus; Phorbol ester; Protein kinase C; Tumor promoter

Indexed keywords

CARCINOGEN; EPSTEIN BARR VIRUS EARLY ANTIGEN; EPSTEIN-BARR VIRUS EARLY ANTIGEN; PHORBOL DIBUTYRATE; PROTEIN KINASE C; SUPEROXIDE; VIRUS ANTIGEN;

ARTICLE; CHEMISTRY; DRUG EFFECT; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIGENS, VIRAL; CARCINOGENS; PHORBOL 12,13-DIBUTYRATE; PROTEIN KINASE C; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES;

EID: 0034330917     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.64.2429     Document Type: Article

References (32)

1. Hoppe, W., Brandel, F., Strell, I., Rohrl, M., Gassmann, J., Hecker, E., Bartsch, H., Kreibich, G., and Szczepanski, C., Rontgenstrukturanalyse des Neophorbols. Angew. Chem., 19, 824 (1967).
2. Driedger, P. E. and Blumberg, P. M., Specific binding of phorbol ester tumor promoters. Proc. Natl. Acad. Sci. USA, 11, 567-571 (1980).
3. For a review, see: Wender, P. A. and Cribbs, C. M., Computer assisted molecular design related to the protein kinase C receptor. Adv. Med. Chem., 1, 1-53 (1992)
4. Wender, P. A., Koehler, K. F., Sharkey, N. A., DelPAquila, M. L., and Blumberg, P. M., Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogs. Proc. Natl. Acad. Sci. USA, 83, 4214-4220 (1986).
5. Yamasaki, H., Weinstein, I. B., and van Duuren B. L., Induction of erythroleukemia cell adhesion by plant diterpene tumour promoters: a quantitative study and correlation with in vivo activities. Carcinogenesis, 2, 537-543 (1981).
6. Nishizuka, Y., The role of protein kinase C in cell surface signal transduction and tumor promotion. Nature, 308, 693-698 (1984).
7. Irie, K., Ishii, T., Ohigashi, H., Wender, P. A., Miller, B. L., and Takeda, N., Synthesis and characterization of new photolabile phorbol esters for affinity labeling of protein kinase C. J. Org. Chem., 61, 2164-2173 (1996).
8. Uotsu, K., Sodeoka, M., and Shibasaki, M., Photoaffinity labeling of PKC isozymes by phorbol derivatives. Bioorg. Med. Chem., 6, 1117-1126 (1998).
9. Wang, S., Kazanietz, M. G., Blumberg, P. M., Marquez, V. E., and Milne, G. W. A., Molecular modeling and site-directed mutagenesis studies of a phorbol ester-binding site in protein kinase C. J. Med. Chem., 39, 2541-2553 (1996).
10. Ohigashi, H., Kaji, M., and Koshimizu, K., Mouse leukemia P388 cell proliferation inhibitor, membra-nin, from Maprounea membranacea. In “Search for useful plants in tropical rain forest Cameroon, and chemical studies on biologically active substances of the plants (part II)”, eds. Koshimizu, K., Report of the Field Investigation supported by a Grant-in-Aid for Overseas Scientific Survey from the Ministry of Education, Science and Culture of Japan, No. 60041040 (1985) and No. 61043036 (1986), pp. 86-97 (1987)
11. Koshimizu, K., Ohigashi, H., Kaji, M., Yanagi, Y., Japan Kokai Tokkyo Koho, S63-218678 (1988).
12. Kogiso, S., Wada, K., and Munakata, K., Odoracin, a nematicidal constituent from Daphne odora. Agric. Biol. Chem., 40, 2119-2120 (1976).
13. Gustafson, K. R., Cardellina, II J. H., McMahon, J. B., Gulakowski, R. J., Ishitoya, J., Szallasi, Z., Lewin, N. E., Blumberg, P. M., Weislow, O. S., Beutler, J. A., Buckheit, R. W., Cragg, G. M., Cox, P. A., Bader, J. P., and Boyd, M. R., A nonpromoting phorbol from the Samoan medicinal plant Homalanthus nutans inhibits cell killing by HIV-1. J. Med. Chem., 35, 1978-1986 (1992).
14. Sorg, B., Fürstenberger, G., Berry, D. L., Hecker, E., and Marks, F., Preparation of retinoic acid esters of phorbol derivatives. J. Lipid Res., 23, 443-447 (1982).
15. Lee, H. Y., Synthetic and pharmacological studies on tumor promoters: synthesis of phorbol and phorbol analogs. Ph. D. dissertation, Stanford University (1988).
16. Ito, Y., Yanase, S., Fujita, J., Harayama, T., Takashima, M., and Imanaka, H., A short-term in vitro assay for tumor promoter substances using human lymphoblastoid cells latently infected with Epstein-Barr virus. Cancer Lett., 13, 29-37 (1981).
17. zur Hausen, H., Bornkamm, G. W., Schmidt, R., and Hecker, E., Tumor initiators and promoters in the induction of Epstein-Barr virus. Proc. Natl. Acad. Sci. USA, 76, 782-785 (1979).
18. 2“production by human neutrophils. The preparation and assay of NADPH oxidase-containing particles from human neutrophils. Methods Enzy mo I., 105, 358-365 (1984).
19. Nakamura, Y., Murakami, A., Ohto, Y., Torikai, K., Tanaka, T., and Ohigashi, H., Suppression of tumor promoter-induced oxidative stress and inflammatory responses in mouse skin by a superoxide generation inhibitor l'-acetoxychavicol acetate. Cancer Res., 58, 4832-4839 (1998).
20. Irie, K., Oie, K., Nakahara, A., Yanai, Y., Ohigashi, H., Wender, P. A., Fukuda, H., Konishi, H., and Kikkawa, U., Molecular basis for protein kinase C isozyme-selective binding: the synthesis, folding, and phorbol ester binding of the cysteine-rich domains of all protein kinase C isozymes. J. Am. Chem. Soc., 120, 9159-9167 (1998)
21. Wender, P. A., Irie, K., and Miller, B. L., Identification, activity, and structural studies of peptides incorporating the phorbol ester binding domain of protein kinase C. Proc. Natl. Acad. Sci. USA, 92, 239-243 (1995).
22. 3H]phorbol 12,13-dibutyrate binding. Cancer Res., 45, 19-24 (1985).
23. Irie, K., Isaka, T., Iwata, Y., Yanai, Y., Nakamura, Y., Koizumi, F., Ohigashi, H., Wender, P. A., Satomi, Y., and Nishino, H., Synthesis and biological activities of new conformationally restricted analogues of (-)-indolactam-V: elucidation of the biologically active conformation of the tumor promoting teleocidins. J. Am. Chem. Soc., 118, 10733-10743 (1996).
24. Reiners, Jr., J. J., Pence, B. C., Barcus, M. C. S., and Cantu, A. R., 12-O-Tetradecanoylphorbol-13-acetate-dependent induction of xanthine dehydrogenase and conversion to xanthine oxidase in murine epidermis. Cancer Res., 47, 1775-1779 (1987).
25. Cross, A. R. and Jones, O. T. G., Enzymatic mechanisms of superoxide production. Biochim. Biophys. Acta, 1057, 1775-1779 (1987).
26. Ono, Y., Fujii, T., Igarashi, K., Kuno, T., Tanaka, C., Kikkawa, U., and Nishizuka, Y., Phorbol ester binding to protein kinase C requires a cysteine-rich zinc-finger-like sequence. Proc. Natl. Acad. Sci. USA, 86, 4868-4871 (1989).
27. Hurley, J. H., Newton, A. C., Parker, P. J., Blumberg, P. M., and Nishizuka, Y., Taxonomy and function of Cl protein kinase C homology domains. Protein Science, 6, 477-480 (1997).
28. Irie, K., Nakahara, A., Ohigashi, H., Fukuda, H., Wender, P. A., Konishi, H., and Kikkawa, U., Synthesis and phorbol ester-binding studies of the individual cysteine-rich motifs of protein kinase D. Bioorg. Med. Chem. Lett., 9, 2487-2490 (1999).
29. Bögi, K., Lorenzo, P. S., Ács, P., Szállási, Z., Wagner, G. S., and Blumberg, P. M., Comparison of the roles of the Cla and Clb domains of protein kinase C alpha in ligand induced translocation in NIH 3T3 cells. FEBS Lett., 456, 27-30 (1999).
30. Rose-John, S., Dietrich, A., and Marks, F., Molecular cloning of mouse protein kinase C (PKC) cDNA from Swiss 3T3 fibroblasts. Gene, 74, 465-471 (1988).
31. Tang, Y.-M. and Ashendel, C. L., Isolation of cloned mouse protein kinase C beta-II cDNA and its sequence. Nucleic Acids Res., 18, 5310 (1990).
32. Hecker, E., Szczepanski, C. V., Kubinyi, H., Bresch, H., Härle H, Schairer, H. U., and Bartsch, H., Über die Wirkstoffe des Crotonöls, VII, Phorbol. Z. Natur-forschg., 21b, 1204-1214 (1966).