Mechanism-based inactivation of cytochrome P450 2B4 by aldehydes: Relationship to aldehyde deformylation via a peroxyhemiacetal intermediate

Biochemistry

Volumn 36, Issue 16, 1997, Pages 4895-4902

  Raner, Gregory M ^a   Chiang, Eric W ^a   Vaz, Alfin D N ^a   Coon, Minor J ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CYTOCHROME P450; HEME DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; BLEACHING; CHROMATOPHORE; DIALYSIS; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME INACTIVATION; PRIORITY JOURNAL; PROTEIN SECONDARY STRUCTURE; PROTEIN TERTIARY STRUCTURE;

ALDEHYDES; ARYL HYDROCARBON HYDROXYLASES; ASCORBIC ACID; CATALASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DEUTERIUM; ENZYME INHIBITORS; EPOXIDE HYDROLASES; FREE RADICALS; GLUTATHIONE; MODELS, CHEMICAL; MUTATION; NADP; STEROID HYDROXYLASES; SUPEROXIDE DISMUTASE;

EID: 0030995094     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9630568     Document Type: Article

References (36)

1. Akhtar, M., Calder, M. R., Corina, D. L., & Wright, J. N. (1982) Biochem. J. 201, 569-580.
2. Cole, P. A., & Robinson, C. H. (1990) J. Med. Chem. 33, 2933-2942.
3. Coon, M. J., van der Hoeven, T. A., Dahl, S. B., & Haugen, D. A. (1978) Methods Enzymol. 52, 109-117.
4. Davis, S. C., Sui, Z., Peterson, J. A., & Ortiz de Montellano, P. R. (1996) Arch. Biochem. Biophys. 328, 35-42.
5. DeMaster, E. G., Shirota, F. N., & Nagasawra, H. T. (1986) Biochem. Pharmacol. 35, 1481-1489.
6. French, J. S., & Coon, M. J. (1979) Arch. Biochem. Biophys. 195, 565-577.
7. Imai, M., Shimada, H., Watanabe, Y., Matsushima-Hibiya, Y., Makino, R., Koga, H., Horiuchi, T., & Ishimura, Y. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 7823-7827.
8. Ji, C., Mirvish, S. S., Nickols, J., Ishizaki, H., Lee, M. J., & Yang, C. S. (1989) Cancer Res. 49, 5299-5304.
9. Lindahl, R., & Peterson, D. R. (1991) Biochem. Pharmacol. 41, 1583-1587.
10. Marinello, A. J., Bansal, S. K., Paul, B., Koser, P. L., Love, J., Struck, R. F., & Gurtoo, H. L. (1984) Cancer Res. 44, 4165-4621.
11. Martinis, S. A., Atkins, W. M., Stayton, P. S., & Sugar, S. G. (1989) J. Am. Chem. Soc. 111, 9252-9253.
12. Oh, S. S., & Robinson, C. H. (1993) J. Steroid Biochem. Mol. Biol. 44, 389-397.
13. Ortiz de Montellano, P. R., & Mico, B. A. (1980) Mol. Pharmacol. 18, 128-135.
14. Ortiz de Montellano, P. R., & Kunze, K. L. (1981) Biochemistry 20, 7266-7271.
15. Ortiz de Montellano, P. R., Kunze, K. L., Beilan, H. S., & Wheeler, C. (1982) Biochemistry 21, 1331-1339.
16. Ortiz de Montellano, P. R., Mangold, B. L. K., Wheeler, C., Kunze, K. L., & Reich, N. O. (1983) J. Biol. Chem. 258, 4208-4213.
17. Osawa, Y., Martin, B. M., Griffin, P. R., Yates, J. R., III, Shabanowitz, J., Hunt, D. F., Murphy, A. C., Chen, L., Cotter, R. J., & Pohl, L. R. (1990) J. Biol. Chem. 265, 10340-10346.
18. Osawa, Y., Fellows, C. S., Meyer, C. A., Woods, A., Castoro, J. A., Cotter, R. J., Wilkins, C. L., & Highet, R. J. (1994) J. Biol. Chem. 269, 15481-15487.
19. Patel, J. M., Harper, C., & Drew, R. T. (1978) Drug Metab. Dispos. 6, 368-374.
20. Pernecky, S. J., Olken, N. M., Bestervelt, L. L., & Coon, M. J. (1995) Arch. Biochem. Biophys. 318, 446-456.
21. Raner, G. M., Vaz, A. D. N., & Coon, M. J. (1996) Mol. Pharmacol. 49, 515-522.
22. Roberts, E. S., Vaz, A. D. N., & Coon, M. J. (1991) Proc. Natl. Acad. Sci. U.S.A. 88, 8963-8966.
23. Roberts, E. S., Vaz, A. D. N., & Coon M. J. (1992) Mol. Pharmacol. 41, 427-433.
24. Skinner, S. J. M., & Akhtar, M. (1969) Biochem. J. 114, 75-81.
25. Stevenson, D. E., Wright, J. N., & Akhtar, M. (1988) J. Chem. Soc. Perkin Trans. 1 2043-2052.
26. Swinney, D. C., & Mak, A. Y. (1994) Biochemistry 33, 2185-2190.
27. Terelius, Y., Norsten-Hoog, C., Cronholm, T., & Ingelman-Sundberg, M. (1991) Biochem. Biophys. Res. Commun. 179, 689-694.
28. Vaz, A. D. N., & Coon, M. J. (1994) Biochemistry 33, 6442-6449.
29. Vaz, A. D. N., Roberts, E. S., & Coon, M. J. (1991) J. Am. Chem. Soc. 113, 5886-5887.
30. Vaz, A. D. N., Kessell, K. J., & Coon, M. J. (1994) Biochemistry 33, 13651-13661.
31. Vaz, A. D. N., Pernecky, S. J., Raner, G. M., & Coon, M. J. (1996) Proc. Natl. Acad. Sci. U.S.A. 93, 4644-4648.
32. Watanabe, K., Narimatsu, S., Yamamoto, I., & Yoshimura, H. (1990) Biochem. Biophys. Res. Commun. 166, 1308-1312.
33. Watanabe, K., Narimatsu, S., Yamamoto, I., & Yoshimura, H. (1991) J. Biol. Chem. 266, 2709-2711.
34. Watanabe, K., Matsunaga, T., Narimatsu, S., Yamamoto, I., & Yoshimura, H. (1992) Biochem. Biophys. Res. Commun. 188, 114-119.
35. Weiner, H. (1979) in Biochemistry and Pharmacology of Ethanol (Majchrowicz, E., Noble, E. P., Eds.), Vol. 1, pp 107-124, Plenum Press, New York.
36. White, I. N. H. (1982) Chem.-Biol. Interact. 39, 231-243.