Oxidation of butadiene monoxide to meso- and (±)-diepoxybutane by cDNA- expressed human cytochrome P450s and by mouse, rat, and human liver microsomes: Evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes

Archives of Biochemistry and Biophysics

Volumn 337, Issue 2, 1997, Pages 176-184

  Krause, Renee J ^a   Elfarra, Adnan A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

1,3 butadiene; butadiene monoxide; human liver microsomes; meso and ( ) diepoxybutane; P450 reactions

Indexed keywords

1,3 BUTADIENE; BUTADIENE DIEPOXIDE; CHLORZOXAZONE; COMPLEMENTARY DNA; CYTOCHROME P450; EPOXIDE HYDROLASE;

ANIMAL CELL; ARTICLE; CARCINOGENICITY; CONTROLLED STUDY; DIASTEREOISOMER; GAS CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDRATION; HYDROLYSIS; LIVER MICROSOME; MALE; MASS SPECTROMETRY; MICHAELIS MENTEN KINETICS; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; RISK ASSESSMENT; STEREOCHEMISTRY;

ANIMALIA;

EID: 0031568224     PISSN: 00039861     EISSN: None     Source Type: Journal    
DOI: 10.1006/abbi.1996.9781     Document Type: Article

References (43)

1. 1. Stump, F. D., and Dropkin, D. L. (1985) Anal. Chem. 57, 2629-2634.
2. 2. Brunneman, K. D., Kagan, M. R., Cox, J. E., and Hoffman, D. (1990) Carcinogenesis 11, 1863-1868.
3. 3. (1990) Fed. Reg. 55, 32736-32826.
4. 4. Santos-Burgoa, C., Matanoski, G. M., Zeger, S., and Schwartz, L. (1992) Am. J. Epidemiol. 136, 843-854.
5. 5. Ward, J. B., Ammenheuser, M. M., Bechtold, W. E., Whorton, E. B., and Legator, M. S. (1994) Environ. Health Perspect. 102(Suppl. 9), 79-85.
6. 6. Melnick, R. L., Huff, J., Chou, B. J., and Miller, R. A. (1990) Cancer Res. 50, 6592-6599.
7. 7. Owen, P. E., Glaister, J. R., Gaunt, I. F., and Pullinger, D. H. (1987) Ind. Hyg. Assoc. J. 48, 407-413.
8. 8. Elfarra, A. A., Duescher, R. J., and Pasch, C. M. (1991) Arch. Biochem. Biophys. 286, 244-251.
9. 9. Sharer, J. E., Duescher, R. J., and Elfarra, A. A. (1992) Drug Metab. Dispos. 20, 658-664.
10. 10. Duescher, R. J., and Elfarra, A. A. (1994) Arch. Biochem. Biophys. 311, 342-349.
11. 11. Duescher, R. J., and Elfarra, A.A. (1992) J. Biol. Chem. 267, 19859-19865.
12. 12. Citti, L., Gervasi, P. G., Turchi, G., Bellucci, G., and Bianchini, R. (1984) Carcinogenesis 5, 47-52.
13. 13. Selzer, R. R., and Elfarra, A. A. (1996) Chem. Res. Toxicol. 9, 126-132.
14. 14. Selzer, R. R., and Elfarra, A. A. (1996) Chem. Res. Toxicol. 9, 875-881.
15. 15. Sharer, J. E., and Elfarra, A.A. (1992) Chem. Res. Toxicol. 5, 787-790.
16. 16. Sharer, J. E., Duescher, R. J., and Elfarra, A. A. (1991) Chem. Res. Toxicol. 4, 430-436.
17. 17. Elfarra, A. A., Sharer, J. E., and Duescher, R. J. (1995) Chem. Res. Toxicol. 8, 68-76.
18. 18. Duescher, R. J., Sharer, J. E., and Elfarra, A. A. (1993) Pharmacologist 35, 202.
19. 19. Elfarra, A. A., Krause, R. J., and Selzer, R. R. (1996) Toxicology 113, 23-30.
20. 20. Thornton-Manning, J., Dahl, A. R., Bechtold, W. E., Griffith, W. C., Jr., and Henderson, R. F. (1995) Carcinogenesis 16, 1723-1731.
21. 21. Csanàdy, G. A., Guengerich, F. P., and Bond, J. A. (1992) Carcinogenesis 13, 1143-1153.
22. 22. Cochrane, J. E., and Skopek, T. R. (1994) Carcinogenesis 15, 713-717.
23. 23. Van Duren, B. L., Orris, L., and Nelson, N. (1965) J. Natl. Cancer Inst. 35, 707-717.
24. 24. Ötvös, L., and Elekes, I. (1975) Tetrahedron Lett. 29, 2481-2484.
25. 25. Elfarra, A. A., and Duescher, R. J. (1995) Toxicologist 15, 61.
26. 26. Buckingham, J. (Ed.) (1982) Dictionary of Organic Compounds, 5th ed., p. 671, Chapman & Hill, New York.
27. 27. Van Duuren, B. L., Nelson, N., Orris, L., Palmes, E. D., and Schmit, F. L. (1963) J. Natl. Cancer Inst. 31, 41-55.
28. 28. Waxman, D. J., Lapenson, D. P., Aoyama, T., Gelboin, H. V., Gonzalez, F. J., and Korzekwa, K. (1991) Arch. Biochem. Biophys. 290, 160-166.
29. 29. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) J. Biol. Chem., 193, 265-275.
30. 30. Yamazaki, H., Guo, Z., and Guengerich, F. P. (1995) Drug Metab. Dispos. 23, 438-440.
31. 31. Clarke, S., Baldwin, S., Bloomer, J., Ayrton, A., Sozio, R., and Chenery, R. J. (1994) Chem Res. Toxicol. 7, 836-842.
32. 32. Malvoisin, E., and Roberfroid, M. (1982) Xenobiotica 12, 137-144.
33. 33. Malvoisin, E., Evrard, E., Roberfroid, M., and Mercier, M. (1979) J. Chromatogr. 186, 81-87.
34. 34. Seaton, M. J., Follansbee, M. H., and Bond, J. A. (1995) Carcinogenesis 16, 2287-2293.
35. 35. Wrighton, S. A., and Stevens, J. C. (1992) Crit. Rev. Toxicol. 22, 1-21.
36. 36. Gonzalez, F. J., and Gelboin, H. V. (1994) Drug Metab. Rev. 26, 165-183.
37. 37. Guengerich, F. P. (1992) Life Sci 50, 1471-1478.
38. 38. Shimada, T., Yamazaki, H., Mimura, M., Inui, Y., and Guengerich, F. P. (1994) J. Pharmacol. Exp. Ther. 270, 414-423.
39. 39. Yamazaki, H., Nakano, Y., Imai, Y., Ueng, Y., Guengerich, F. P., and Shimada, T. (1996) Arch. Biochem. Biophys. 325, 174-182.
40. 40. Delaforge, M., Jaouen, M., and Mansuy, D. (1984) Chem. Biol. Interact. 51, 371-376.
41. 41. Chang, T. K., Gonzalez, F. J., and Waxman, D. J. (1994) Arch. Biochem. Biophys. 311, 437-442.
42. 42. Newton, D. J., Wang, R. W., and Lu, A. Y. (1995) Drug Metab. Dispos. 23, 154-158.
43. 43. Yang, C. S., Brady, J. F., and Hong, J. (1992) FASEB J. 6, 737-744.