Identification of the heme adduct and an active site peptide modified during mechanism-based inactivation of rat liver cytochrome P450 2B1 by secobarbital

Chemical Research in Toxicology

Volumn 9, Issue 3, 1996, Pages 614-622

  He, Kan ^d   Falick, Arnold M ^a,b   Chen, Baili ^d   Nilsson, Fredrik ^a,c   Correia, Maria Almira ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b PerSeptive Biosystems   (United States)

^c KAROLINSKA INSTITUTE   (Sweden)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

BARBITURIC ACID DERIVATIVE; CYTOCHROME P450; HEME; PROTEINASE; PROTOPORPHYRIN; SECOBARBITAL;

ABSORPTION SPECTROSCOPY; ALKYLATION; ANIMAL TISSUE; ARTICLE; ENZYME ACTIVE SITE; ENZYME INACTIVATION; ENZYME RECONSTITUTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; NONHUMAN; RAT;

AMINO ACID SEQUENCE; ANIMALS; ARYL HYDROCARBON HYDROXYLASES; BINDING SITES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 CYP2B1; CYTOCHROME P-450 ENZYME SYSTEM; ELECTROPHORESIS; HEME; MALE; MASS SPECTROMETRY; MICROSOMES, LIVER; MOLECULAR SEQUENCE DATA; OXIDOREDUCTASES; PEPTIDE FRAGMENTS; PEPTIDE MAPPING; RATS; RATS, SPRAGUE-DAWLEY; SECOBARBITAL; STEROID HYDROXYLASES;

ANIMALIA;

EID: 0029862643     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950177k     Document Type: Article

References (34)

1. Ortiz de Montellano, P. R. (1995) Biotransformations of Drugs and Chemicals. In Encyclopedia of Molecular Biology and Biotechnology (Meyers, R. A., Ed.) VCH, New York, in press.
2. Halpert, J. R., Guengerich, F. P., Bend, J R., and Correia, M. A. (1994) Selective inhibitors of cytochromes P450. Toxicol Appl. Pharmacol. 125, 163-175.
3. Halpert, J. R. (1995) Structural basis of selective cytochrome P450 inhibition. Annu. Rev. Pharmacol. Toxicol. 35, 29-54 and references therein.
4. Ortiz de Montellano, P. R., and Correia, M. A. (1995) Inhibition of cytochrome P450 enzymes. In Cytochrome P450: Structure, Function, and Mechanism (Ortiz de Montellano, P. R., Ed.) 2nd ed., Plenum Press, New York, pp 305-363, and references therein.
5. Lunetta, J. M., Sugiyama, K., and Correia, M. A. (1989) Secobarbital-mediated inactivation of rat liver cytochrome P-450b: A mechanistic reappraisal. Mol. Pharmacol. 35, 10-17.
6. Waxman, D. J., and Walsh, C. T. (1982) Phenobarbital-induced rat liver cytochrome P-450. J. Biol. Chem. 257, 10446-10457.
7. Walsh, C. T. (1982) Suicide substrates, mechanism-based enzyme inactivators: Recent developments. Annu. Rev. Biochem. 53, 493-535.
8. Levin, W., Sernatinger, E., Jacobson, M., and Kuntzman, R. (1973) Breakdown of cytochrome P-450 by secobarbital and other allyl-containing barbiturates. Drug Metab. Dispos. 1, 275-285 and references therein.
9. De Matteis, F., and Cantoni, L. (1979) Alteration of the porphyrin nucleus of cytochrome P450 caused in the liver by treatment with allyl-containing drugs. Biochem. J. 183, 99-103.
10. Shephard, E. A., Pike, S. F., Rabin, B. R., and Phillips, I. R. (1983) A rapid one-step purification of NADPH-cytochrome c (P450) reductase from rat liver microsomes. Anal. Biochem. 129, 430-433.
11. Correia, M. A., Decker, C., Sugiyama, K., Underwood, M., Bornheim, L., Wrighton, S. A., Rettie, A. E., and Trager, W. F. (1987) Degradation of rat hepatic cytochrome P-450 heme by 3,5-dicarbethoxy-2,6-dimethyl-4-ethyl-1,4-dihydropyridine to irreversibly bound protein adducts. Arch. Biochem. Biophys. 258, 436-451.
12. Lubet, R. A., Mayer, R. T., Cameron, J. W., Nims, R. W., Burke, M. D., Wolff, T., and Guengerich, F. P. (1985) Dealkylation of pentoxyresorufin: A rapid and sensitive assay for measuring induction of cytochrome(s) P-450 by phenobarbital and other xenobiotics in the rat. Arch. Biochem. Biophys. 238, 43-48.
13. Underwood, M. C., Cashman, J. R., and Correia, M. A. (1992) Specifically designed thiosteroids as active site-directed probes for functional dissection of cytochrome P-450 3A isozymes. Chem. Res. Toxicol. 5, 42-53.
14. Sokoloff, R. L., and Frigon, R. P. (1981) Rapid spectrophotometric assay of dodecyl sulfate using acridine orange. Anal. Biochem. 118, 138-141.
15. Yao, K., Falick, A. M., Patel, N., and Correia, M. A. (1993) Cumene hydroperoxide-mediated inactivation of cytochrome P450 2B1: Identification of an active site heme-modified peptide. J. Biol. Chem. 268, 59-65.
16. Schagger, H., and van Jagow, G. (1987) Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range of 1 to 100 kDa. Anal. Biochem. 166, 368-379.
17. Medzihradszky, K. F., Maltby, D A., Hall, S. C., Settineri, C. A., and Burlingame, A. L. (1994) Characterization of protein N-glycosylation by reversed-phase microbore liquid chromatography/ electrospray mass spectrometry, complementary mobile phases, and sequential exoglycosidase digestion. J. Am Soc. Mass Spectrom. 5, 350-358.
18. 3H-labeled 2-ethynylnaphthalene-inactivated P450 2B1 and 2B4 using amino acid sequencing and mass spectrometry. Biochemistry 33, 3766-3771.
19. Ortiz de Montellano, P. R. (1992) Mechanism-based inactivation of cytochrome P450: Isolation and characterization of N-alkyl heme adducts. Methods Enzymol. 206, 533-540.
20. Fujii-Kuryama, Y., Mizukami, Y., Kawajiri, K., Sogawa, K., and Muramatsu, M. (1982) Primary structure of a cytochrome P-450: coding nucleotide sequence of phenobarbital-inducible cytochrome P-450 cDNA from rat liver. Proc. Natl. Acad. Sci U.S.A. 79, 2793-2797.
21. Frey, A. B., Waxman, D. J., and Kreibich, G. (1985) The structure of phenobarbital-inducible rat liver cytochrome P450 isoenzyme PB-4. J. Biol. Chem. 260, 15253-15265.
22. Roberts, E. S., Hopkins, N. E., Alworth, W. L., and Hollenberg, P F (1993) Mechanism-based inactivation of cytochrome P450 2B1 by 2-ethynylnaphthalene: Identification of an active-site peptide. Chem. Res. Toxicol. 6, 470-479.
23. Nelson, D. R., and Strobel, H. W. (1988) On the membrane topology of vertebrate cytochrome P-450 proteins. J. Biol. Chem. 263, 6038-6050.
24. Nelson, D R (1995) Cytochrome P450 nomenclatures and alignment of selected sequences. In Cytochrome P450: Structure, Function, and Mechanism (Ortiz de Montellano, P. R., Ed.) 2nd ed . Plenum Press, New York, pp 575-606.
25. Yun, C.-H., Martin, M. V., Hopkins, N. E., Alworth, W. L., Hammons, G. J., and Guengerich, F. P. (1992) Modification of cytochrome P4501A2 enzymes by the mechanism-based inactivator 2-ethynylnaphthalene. Biochemistry 31, 10556-10563.
26. cam. J. Mol. Biol. 195, 687-700.
27. Ortiz de Montellano, P. R., Yost, G. S., Mico, B. A., Dinizo, S. E., Correia, M. A., and Kumbara, H. (1979) Destruction of cytochrome P-450 by 2-isopropyl-4-pentenamide and methyl-2-isopropyl-4-pentenoate: mass spectrometric characterization of prosthetic heme adducts and non-participation of epoxide metabolites. Arch. Biochem. Biophys. 197, 524-533.
28. Kunze, K. L., Mangold, B. L. K., Wheeler, C., Beilan, H. S., and Ortiz de Montellano, P. R. (1983) The cytochrome P-450 active site. J. Biol. Chem. 258, 4202-4207.
29. Tuck, S. F., and Ortiz de Montellano, P. R. (1992) Topological mapping of the active sites of cytochromes P4502B1 and P4502B2 by in situ rearrangement of their aryl-iron complexes. Biochemistry 31, 6911-6916.
30. BM-3): In situ rearrangement of their phenyl-iron complexes. J. Biol. Chem. 267, 5614-5620.
31. Tuck, S. F., Hiroya, K., Shimizu, T., Hatano, M., and Ortiz de Montellano, P. R. (1993) The cytochrome P450 1A2 (CYP1A2) active site: Topology and perturbations caused by Glu-318 and Thr-319 mutations. Biochemistry 32, 2548-2553.
32. Swanson, B. A., Dutton, D. R., Yang, C. S., and Ortiz de Montellano, P. R. (1991) The active sites of cytochromes P450 IA1, IIB1, IIB2, and IIE1. Topological analysis by in situ rearrangement of phenyl-iron complexes. J. Biol. Chem. 266, 19258-19264.
33. Swanson, B. A., Halpert, J. R., Bornheim, L. M., and Ortiz de Montellano, P. R. (1992) Topological analysis of the active sites of cytochromes P450IIB4 (rabbit), P450IIB10 (mouse) and P450IIB11 (dog) by in situ rearrangement of phenyl-iron complexes. Arch. Biochem. Biophys. 292, 42-46.
34. Correia, M. A. (1993) Drug-mediated heme-modification of cytochrome P450 apoproteins: Structural characterization and physiological implications. Toxicologist 13, 15.