Stereoselective epoxidation and hydration at the K-region of polycyclic aromatic hydrocarbons by cDNA-expressed cytochromes P450 1A1, 1A2, and epoxide hydrolase

Biochemistry

Volumn 35, Issue 49, 1996, Pages 15807-15813

  Shou, M ^a   Gonzalez, F J ^a   Gelboin, H V ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7,12 DIMETHYLBENZ[A]ANTHRACENE; BENZ[A]ANTHRACENE; BENZO[A]PYRENE; BENZO[C]PHENANTHRIDINE DERIVATIVE; CHRYSENE; COMPLEMENTARY DNA; CYTOCHROME P450; DIBENZ[A,H]ANTHRACENE; EPOXIDE HYDROLASE; POLYCYCLIC AROMATIC HYDROCARBON; TRICHLOROPROPYLENE OXIDE;

ANIMAL CELL; ARTICLE; CARCINOGENICITY; CONTROLLED STUDY; ENANTIOMER; ENZYME MECHANISM; EPOXIDATION; HEP 2 CELL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDRATION; INSECT; MOUSE; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

ANIMALS; ANTHRACENES; BACULOVIRIDAE; CHRYSENES; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; DIHYDROXYDIHYDROBENZOPYRENES; ENZYME INHIBITORS; EPOXIDE HYDROLASES; EPOXY COMPOUNDS; GENE EXPRESSION; HUMANS; MICE; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; RECOMBINANT PROTEINS; TRICHLOROEPOXYPROPANE; VACCINIA VIRUS;

ANIMALIA; INSECTA; VACCINIA; VACCINIA VIRUS;

EID: 0029758268     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi962042z     Document Type: Article

References (43)

1. Battula, N., Sagara, J., & Gelboin, H. V. (1987) Proc. Natl. Acad. Sci. U.S.A. 84, 4073.
2. Bauer, E., Guo, Z., Ueng, Y-F., Bell, L. C., Zeldin, D., & Guengerich, F. P. (1995) Chem. Res. Toxicol. 8, 136.
3. Buening, M. K., Wislocki, P. G., Levin, W., Yagi, D. R., Thakker, D. R., Akagi, H., Koreeda, M., Jerina, D. M., & Conney, A. H. (1978) Proc. Natl. Acad. Sci. U.S.A. 75, 5358.
4. Buters, J. T. M., Shou, M., Hardwick, J. P., Korzekwa, K. R., & Fonzalez, F. J. (1995) Drug Metab. Disp. 23, 696.
5. Chakrabarti, S., Brechling, K., & Moss, B. (1985) Mol. Cell. Biol. 5, 3403.
6. Chiu, P. L. Weems, H. B., Wong, T. K., Fu, P. P., & Yang, S. K. (1983) Chem.-Biol. Interact. 44, 155.
7. Conney, A. H. (1982) Cancer Res. 46, 5084.
8. Dipple, A. (1985) Polycyclic Hydrocarbons and Carcinogenesis (Harvey, R. G., Ed.) pp 1-17, American Chemical Society, Washington, DC.
9. Gelboin, H. V. (1980) Physiol. Rev. 60, 1107.
10. Gonzalez, F. J. (1989) Pharmacol. Rev. 40, 243.
11. Gonzalez, F. J., & Korzekwa, K. R. (1995) Annu. Rev. Pharmacol. Toxicol. 35, 369.
12. Gonzalez, F. J., Crespi, C. L., & Gelboin, H. V. (1991a) Mutat. Res. 247, 113.
13. Gonzalez, F. J. Aoyama, T., & Gelboin, H. V. (1991b) Methods Enzymol. 206, 85.
14. Grant, M. H., Duthie, S. J., Gray, A. G., & Burke, D. M. (1988) Biochem. Pharmacol. 37, 4111.
15. Guengerich, G. P., & Shimada, T. (1991) Chem. Res. Toxicol. 4, 391.
16. Guzelian, P. S. (1988), Microsomes and Drug Oxidations edited by Miners, J. O., Birkett, D. J., Drew, R., & McManus, M., Eds.) p 148, Taylor & Francis, London.
17. Jerina, D. M., & Daly, J. W. (1974) Science 185, 573.
18. Jerina, D. M., Yagi, H., Thakker, D. R., Karle, J. M., Man, H. D., Boyd, D. R., Gadaginamath, G., Wood, A. W., Buening, M., Chang, R. L., Levin, W., & Conney, A. H. (1978) in Advances in Pharmacology and Therapeutics (Cohen, Y., Ed.) Vol. 9, p 53, Oxford Pergamon Press, Oxford.
19. Jerina, D. M., Michaud, D. P., Feldmann, R. J., Armstrong, R. N., Vyas, K. P., Thakker, D. R., Yagi, H., Thomas, P. E., Ryan, D. E., & Levin, W. Microsomes, Drug Oxidations and Drug Toxicity (Sato, R., & Kato, R., Eds.) p 195, Japan Scientific Societies Press, Tokyo.
20. Jones, J. P., Shou, M., & Korzekwa, K. R. (1995) Biochemistry 34, 6956.
21. Levin, W., Buening, M. K., Wood, A. W., Chang, R. L., Kedzierski, B., Thakker, D. R., Boyd, D. R., Gadaginamath, G. S., Armstrong, R. N., Yagi, H., Karle, J. M., Slaga, T. J., Jerina, D. M., & Conney, A. H. (1980) J. Biol. Chem. 255, 9067.
22. Lu, A. Y. H., Jerina, D. M., & Levin, W. (1977) J. Biol. Chem. 252, 3715.
23. Mushtaq, M., Weems, H. B., & Yang, S. K. (1986) Arch. Biochem. Biophys. 246, 478.
24. Mushtaq, M., & Yang, S. K. (1987) Carcinogenesis 8, 705.
25. Mushtaq, M., Weems, H. B., & Yang, S. K. (1989) Chem. Res. Toxicol. 2, 84.
26. Oesch, F. (1972) Xenobiotica 3, 305.
27. Okey, A. B. (1990) Pharmac. Ther. 45, 241.
28. Omura, T., & Sato, R. (1964) J. Biol. Chem. 239, 2370.
29. Shou, M., Korzekwa, K. R., Crespi, C. L., Gonzalez, F. J., & Gelboin, H. V. (1994a) Mol. Carcinog. 10, 159.
30. Shou, M., Korzekwa, K. R., Krausz, K. W., Crespi, C. L., Gonzalez, F. J., & Gelboin, H. V. (1994b) Cancer Lett. 83, 305.
31. Thomas, P. E., Bandiera, S., Reik, L. M., Maines, S. L., Ryan, D. E., & Levin, W. (1987) Fed. Proc. 46, 2563.
32. Weems, H. B., Mushtaq, M., & Yang, S. K. (1985) Anal. Biochem. 148, 328.
33. Weems, H. B., Mushtaq, M., Fu, P. P., & Yang, S. K. (1986a) J. Chromatogr. 371, 211.
34. Weems, H. B., Fu, P. P., & Yang, S. K. (1986b) Carcinogenesis 7, 1221.
35. Yang, S. K. (1988) Biochem. Pharmacol. 37, 61.
36. Yang, S. K., & Fu, P. P. (1984) Biochem. J. 223, 775.
37. Yang, S. K., Mushtaq, M., & Chiu, P-L. (1985a) Polycyclic Hydrocarbons and Carcinogenesis (Harvey, R. G., Ed.) pp 2-34, American Chemical Society, Washington, DC.
38. Yang, S. K., & Chiu, P. L. (1985b) Arch. Biochem. Biophys. 240, 546.
39. Yang, S. K., Mushtaq, M., Weems, H. B., Miller, D. W., & Fu, P. P. (1987a) Biochem. J. 245, 191.
40. Yang, S. K., & Bao, Z.-P. (1987b) Mol. Pharmacol. 32, 73.
41. Yang, S. K., Mushtaq, M., & Weems, H. B. (1987c) Arch. Biochem. Biophys. 255, 48.
42. Yang, S. K., Mushtaq, M., Bao, Z., Weems, H. B., Shou, M., & Lu, X. L. (1989) J. Chromatogr. 461, 377.
43. Yang, S. K., Weems, H. B., & Mushtaq, M. (1990) Chirality and Biological Activity, p 81, Alan R. Liss, Inc., New York.