Dual stimulatory and inhibitory effects of fluorine-substitution on mutagenicity: An extension of the enamine epoxide theory for activation of the quinoline nucleus

Biological and Pharmaceutical Bulletin

Volumn 20, Issue 6, 1997, Pages 646-650

  Saeki, Ken Ichi ^a   Kawai, Hiroshi ^a   Kawazoe, Yutaka ^a   Hakura, Atsushi ^b  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b EISAI CO LTD   (Japan)

Author keywords

Benzoquinoline; Fluroquinoline; Metabolism; Mutagenicity; phenanthrolin e; Quinoline

Indexed keywords

EPOXIDE; FLUORINE; QUINOLINE DERIVATIVE;

ARTICLE; CELL STIMULATION; CELL TRANSFORMATION; DETOXIFICATION; DNA ADDUCT; DRUG EFFECT; ENZYME METABOLISM; FLUORINATION; GENE MUTATION; GENOTOXICITY; METABOLIC ACTIVATION; MITOSIS INHIBITION; MUTAGENICITY; NONHUMAN; PROTEIN MODIFICATION;

EID: 0030793136     PISSN: 09186158     EISSN: None     Source Type: Journal    
DOI: 10.1248/bpb.20.646     Document Type: Article

References (23)

1. Jerina D. M., Yagi H., Lehr R. E., Thakker D. R., Schaefer-Ridder M., Karle J. M., Levin W., Wood A. W., Chang R. L., Conney A. H., "Polycyclic Hydrocarbons Cancer," Vol. 1, ed. by Gelboin H. V., Ts'o Paul O. P. Academic, New York, 1978, pp. 173-188.
2. Tada M., Takahashi K., Kawazoe Y., Chem. Pharm. Bull., 30, 3834-3837 (1982); idem. Chem.-Biol. Interact., 29, 257-266 (1980); Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 19, 541-546 (1996).
3. Tada M., Takahashi K., Kawazoe Y., Chem. Pharm. Bull., 30, 3834-3837 (1982); idem. Chem.-Biol. Interact., 29, 257-266 (1980); Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 19, 541-546 (1996).
4. Tada M., Takahashi K., Kawazoe Y., Chem. Pharm. Bull., 30, 3834-3837 (1982); idem. Chem.-Biol. Interact., 29, 257-266 (1980); Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 19, 541-546 (1996).
5. The term of K-region of polycyclic aromatic hydrocarbons is widely used to designate the site which is the most electron-rich, hence the most susceptible to oxidative metabolism in the molecule. Since epoxidation at this region was used to be suspected to serve as an activation to ultimate carcinogenic structure, the initial K of Krebs in German was given.
6. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
7. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
8. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
9. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
10. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
11. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
12. LaVoie E. J., Tulley-Freiler L., Bedenko V., Hoffmann D., Mutat. Res., 116, 91-102 (1983); Hecht S. S., LaVoie E. J., Bedenko V., Pingaro L., Katayama S., Hoffmann D., Sardella D. J., Boger E., Lehr R. E., Cancer Res., 41, 4341-4345 (1981); Hubenman E., Slaga T. J., ibid., 39, 411-414 (1979); Diamond L., Cherian K., Harvey R. G., DiGiovanni J., Mutat. Res., 136, 65-72 (1984); Miller E. C., Miler J. A., Cancer Res., 20, 133-137 (1960); Miller J. A., Miller E. C., Finger G. C., ibid., 13, 93-97 (1953); idem, ibid., 17, 387-398 (1957).
13. Takahashi K., Kamiya M., Sengoku Y., Kohda K., Kawazoe Y., Chem. Pharm. Bull., 36, 4630-4633 (1988); Kamiya M., Sengoku Y., Takahashi K., Kohda K., Kawazoe Y., "Antimutagenesis and Anticarcinogenesis," II, ed. by Kuroda Y., Shankel D. M., Waters M. D., Plenum Publishing Corp., New York, 1990, pp. 441-446; Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 16, 232-234 (1993).
14. Takahashi K., Kamiya M., Sengoku Y., Kohda K., Kawazoe Y., Chem. Pharm. Bull., 36, 4630-4633 (1988); Kamiya M., Sengoku Y., Takahashi K., Kohda K., Kawazoe Y., "Antimutagenesis and Anticarcinogenesis," II, ed. by Kuroda Y., Shankel D. M., Waters M. D., Plenum Publishing Corp., New York, 1990, pp. 441-446; Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 16, 232-234 (1993).
15. Takahashi K., Kamiya M., Sengoku Y., Kohda K., Kawazoe Y., Chem. Pharm. Bull., 36, 4630-4633 (1988); Kamiya M., Sengoku Y., Takahashi K., Kohda K., Kawazoe Y., "Antimutagenesis and Anticarcinogenesis," II, ed. by Kuroda Y., Shankel D. M., Waters M. D., Plenum Publishing Corp., New York, 1990, pp. 441-446; Saeki K., Takahashi K., Kawazoe Y., Biol. Pharm. Bull., 16, 232-234 (1993).
16. Saeki K., Tomomitsu M., Kawazoe Y., Momota K., Kimoto H., Biol. Pharm. Bull., 44, 2254-2258 (1996).
17. Kumar S., Sikka H. C., Dubey S. K., Czech A., Geddie N., Wang C.-X., La Voie E. J., Cancer Res., 49, 20-24 (1989).
18. Agarwal S. K., Boyd D. R., Porter H. P., Jennings W. B., Grossman S. J., Jerina D. M., Tetrahedron Lett., 27, 4253-4256 (1986).
19. Saeki K., Kadoi M., Kawazoe Y., Futakuchi M., Tiwawech D., Shirai T., Biol. Pharm. Bull., 20, 40-43 (1997).
20. Araki M., Saneyoshi M., Harada H., Kawazoe Y., Chem. Pharm. Bull., 16, 1742-1746 (1968).
21. Takeuchi I., Hamada Y., Hirota M., Chem. Pharm. Bull., 41, 747-751 (1993).
22. Ames B. N., McCann J., Yamazaki E., Mutat. Res., 31, 347-363 (1975).
23. Takahashi K., Kaiya T., Kawazoe Y., Mutat. Res., 187, 191-197 (1987).