Anti-tumor promoting activity of canventol and its synthetic analogs through inhibition of protein isoprenylation

Japanese Journal of Cancer Research

Volumn 87, Issue 9, 1996, Pages 875-881

  Komori, Atsumasa ^a   Okabe, Sachiko ^a   Suganuma, Masami ^a   Kerr, Michael A ^b   Busch Petersen, Jakob ^b   Oh, Lynette M ^b   Zhuo, Jincong ^b   Kannangara, G S Kamali ^b   Zou, Xianglong ^b   Tius, Marcus A ^b   Fujiki, Hirota ^a  

^a SAITAMA CANCER CENTER   (Japan)

^b UNIVERSITY OF HAWAII   (United States)

Author keywords

Canventol; Mevalonate metabolism; Protein isoprenylation

Indexed keywords

ANTINEOPLASTIC AGENT; CANVENTOL; CHOLESTEROL; LATHOSTEROL; MEVALONIC ACID; OKADAIC ACID; TRITIUM; UBIQUINONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL STRAIN 3T3; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; FEMALE; ISOPRENYLATION; ISOTOPE LABELING; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROCESSING; SKIN CARCINOGENESIS; STEROL SYNTHESIS; TOPICAL DRUG ADMINISTRATION; TUMOR PROMOTION;

EID: 10144228406     PISSN: 09105050     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1349-7006.1996.tb02114.x     Document Type: Article

References (26)

1. Sharma, S., Stuzman, J. D., Kelloff, G. J. and Steele, V. E. Screening of potential chemopreventive agents using biochemical markers of carcinogenesis. Cancer Res., 54, 5848-5855 (1994).
2. Komori, A., Suganuma, M., Okabe, S., Zou, X., Tius, M. A. and Fujiki, H. Canventol inhibits tumor promotion in CD-1 mouse skin through inhibition of tumor necrosis factor a release and of protein isoprenylation. Cancer Res., 53, 3462-3464 (1993).
3. Gibbs, J. B., Oliff, A. and Kohl, N. E. Farnesyl transferase inhibitors: ras research yields a potential cancer therapeutic. Cell, 77, 175-178 (1994).
4. Barbacid, M. ras Genes. Annu. Rev. Biochem., 56, 779-827 (1987).
5. Hancock, J. F., Magee, A. I., Childs, J. E. and Marshall, C. J. All ras proteins are polyisoprenylated but only some are palmitoylated. Cell, 57, 1167-1177 (1989).
6. Gemal, A. L. and Luche, J.-L. Lanthanoids in organic synthesis. 6. The reduction of α-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects. J. Am. Chem. Soc., 103, 5455-5459 (1981).
7. Archer, R. A., Blanchard, W. B., Day, W. A., Johnson, D. W., Lavagino, E. R., Ryan, C. W. and Baldwin, J. E. Cannabinoids. 3. Synthetic approaches to 9-ketocannabinoids. Total synthesis of nabilone. J. Org. Chem., 42, 2277-2284 (1977).
8. Minami, I., Nisar, M., Yuhara, M., Shimizu, I. and Tsuji, J. New methods for the syntheses of alpha, beta-unsaturated ketones, aldehydes, and nitriles by the palladiumcatalyzed reactions of allyl beta-oxo esters, allyl 1-alkenyl carbonates, and allyl alpha-cyano esters. Synthesis, 11, 992-998 (1987).
9. Begbie, A. L. and Golding, B. T. A new synthesis of ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate/Hagemanns ester and its methyl and t-butyl analogues. J. Chem. Soc. Perkin Trans. 1, 4, 602-605 (1972).
10. McMurry, J. E., Fleming, M. P., Kees, K. L. and Krepski, L. R. Titanium-induced reductive coupling of carbonyls to olefins. J. Org. Chem., 43, 3255-3266 (1978).
11. Yamamoto, Y., Furuta, T., Matsuo, J. and Kurata, T. Cleavage of esters under nearly neutral conditions at high pressure. Chemo- and regioselective hydrolysis in organic solvents. J. Org. Chem., 56, 5737-5738 (1991).
12. Roberts, J. L., Borromeo, P. S. and Poulter, C. D. Addition of Eschenmoser's salt to ketone, ester, and lactone enolates. A convenient synthesis of alpha-methylene carbonyls via Mannich intermediates. Tetrahedron Lett., 19, 1621-1624 (1977).
13. Suganuma, M., Fujiki, H., Suguri, H., Yoshizawa, S., Hirota, M., Nakayasu, M., Ojika, M., Wakamatsu, K., Yamada, K. and Sugimura, T. Okadaic acid: an additional non-phorbol-12-tetradecanoate-13-acetate-type tumor promoter. Proc. Natl. Acad. Sci. USA, 85, 1768-1771 (1988).
14. Seabra, M. C., Reiss, Y., Casey, P. J., Brown, M. S. and Goldstein, J. L. Protein farnesyl transferase and geranyl-geranyl transferase share a common a subunit. Cell, 65, 429-434 (1991).
15. ras protein farnesyltransferase. Proc. Natl. Acad. Sci. USA, 88, 732-736 (1991).
16. Faust, J. R., Goldstein, J. L. and Brown, M. S. Synthesis of ubiquinone and cholesterol in human fibroblasts: regulation of a branched pathway. Arch. Biochem. Biophys., 192, 86-99 (1979).
17. Maltese, W. A. and Aprille, J. R. Relation of mevalonate synthesis to mitochondrial ubiquinone content and respiratory function in cultured neuroblastoma cells. J. Biol. Chem., 260, 11524-11529 (1989).
18. Fujiki, H., Suganuma, M., Suguri, H., Yoshizawa, S., Takagi, K. and Kobayashi, M. Sarcophytols A and B inhibit tumor promotion by teleocidin in two-stage carcinogenesis in mouse skin. J. Cancer Res. Clin. Oncol., 115, 25-28 (1989).
19. James, G. L., Goldstein, J. L., Brown, M. S., Rawson, T. E., Somers, T. C., McDowell, R. S., Growley, C. W., Lucas, B. K., Levinson, A. D. and Marsters, Jr. J. C. Benzodiazepine peptidomimetics: potent inhibitors of ras farnesylation in animal cells. Science, 260, 1937-1942 (1993).
20. Grünler, J., Ericsson, J. and Dallner, G. Branch-point reactions in the biosynthesis of cholesterol, dolichol, ubiquinone and prenylated proteins. Biochim. Biophys. Acta, 1212, 259-277 (1994).
21. 2-isopentenyl tRNA from mevalonate in cultured human fibroblasts. J. Biol. Chem., 255, 6546-6548 (1980).
22. Goldstein, J. L. and Brown, M. S. Regulation of the mevalonate pathway. Nature, 343, 427-430 (1990).
23. Ren, Z. and Gould, M. N. Inhibition of ubiquinone and cholesterol synthesis by the monoterpene perillyl alcohol. Cancer Lett., 76, 185-190 (1994).
24. Kohl, N. E., Mosser, S. D., deSolms, S. J., Giuliani, E. A., Pompliano, D. L., Graham, S. L., Smith, R. L., Scolnick, E. M., Oliff, A. and Gibbs, J. B. Selective inhibition of ras-dependent transformation by a farnesyltransferase inhibitor. Science, 260, 1934-1937 (1993).
25. Tamanoi, F. Inhibitors of Ras farnesyltransferases. Trends Biochem. Sci., 18, 349-353 (1993).
26. Hall, A. Small GTP-binding proteins and the regulation of the actin cytoskeleton. Annu. Rev. Cell Biol., 10, 31-54 (1994).