Molecular modelling of CYP2B6, the human CYP2B isoform, by homology with the substrate-bound CYP102 crystal structure: Evaluation of CYP2B6 substrate characteristics, the cytochrome b5 binding site and comparisons with CYP2B1 and CYP2B4

Xenobiotica

Volumn 29, Issue 4, 1999, Pages 361-393

  Lewis, D F V ^a   Lake, B G ^b   Dickins, M ^c   Eddershaw, P J ^c   Tarbit, M H ^c   Goldfarb, P S ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b BIBRA INTERNATIONAL   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 2B4; CYTOCHROME P450 2B6; CYTOCHROME P450 BM3; PENTOXYRESORUFIN DEALKYLASE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; HUMAN; MOLECULAR MODEL; NONHUMAN; RABBIT; RAT;

AMINO ACID SEQUENCE; ANIMALS; ARYL HYDROCARBON HYDROXYLASES; BACTERIAL PROTEINS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 CYP2B1; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; L-LACTATE DEHYDROGENASE; L-LACTATE DEHYDROGENASE (CYTOCHROME); MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; OXIDOREDUCTASES, N-DEMETHYLATING; RABBITS; RATS; SEQUENCE HOMOLOGY, AMINO ACID; STEROID HYDROXYLASES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

ORYCTOLAGUS CUNICULUS;

EID: 0032910377     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982599238560     Document Type: Article

References (106)

1. AOYAMA, T., KORZEKWA, K., NAGATA, K., ADESNIK, M., REISS, A., LAPENSON, D. P., GILLETTE, J., GELBOIN, H. V., WAXMAN, D. J. and GONZALEZ, F. J., 1989, Sequence requirements for cytochrome P450IIB1 catalytic activity. Journal of Biological Chemistry, 264, 21327-21333.
2. ARCHAKOV, A. I. and BACHMANOVA, G. I., 1990, Cytochrome P450 and Active Oxygen (London: Taylor & Francis).
3. BAKER, M. T., OLSON, M. J., WANG, Y., RONNENBERG, W. C., JOHNSON, J. T. and BRADY, A. N., 1995, Isoflurane-chlorodifluoroethene interaction in human liver microsomes: role of cytochrome P4502B6 in potentiation of haloethene metabolism. Drug Metabolism and Disposition, 23, 60-64.
4. BAYLISS, M. K., BELL, J. A., WILSON, K. and PARK, G. R., 1994, 7-ethoxycoumarin O-deethylase kinetics in isolated rat, dog and human hepatocyte suspensions. Xenobiotica, 24, 231-241.
5. BERNHARDT, R., 1995, Cytochrome P450: structure, function and generation of reactive oxygen species. Reviews of Physiology, Biochemistry and Pharmacology, 127, 137-221.
6. BERNHARDT, R., KRAFT, R. and RUCKPAUL, K., 1989, Molecular mechanism of P450-reductase interaction. In I. Schuster (ed.), Cytochrome P450 - Biochemistry and Biophysics (London: Taylor & Francis), pp. 320-323.
7. BLANCK, J., REIN, H., SOMMER, M., RISTAU, O., SMETTAN, G. and RUCKPAUL, K., 1983, Correlations between spin equilibrium shift, reduction rate and N-demethylation activity in liver microsomal cytochrome P450 and a series of benzphetamine analogues as substrates. Biochemical Pharmacology, 32, 1683-1688.
8. BORN, S. L., JOHN, G. H., HARLOW, G. R. and HALPERT, J. R., 1995, Characterization of the progesterone 21-hydroxylase activity of canine cytochrome P450 PBD-2/P450 2B11 through reconstitution, heterologous expression and site-directed mutagenesis. Drug Metabolism and Disposition, 23, 702-707.
9. CAMOLLE, G. P., SHARKAWI, M., DUCHARME, J., MADAN, A., SANZGHIRI, U., PARKINSON, A. and WAINER, I. W., 1996, Role of CYP2B6 and CYP3A4 in the in vitro N-dechloroethylation of ifosfamide. In ISSX Proceedings, 7th North American ISSX Meeting, San Diego, 20-25 October, 1996, vol. 10, p. 361.
10. CHANG, T. K. H., GONZALEZ, F. J. and WAXMAN, D. J., 1994, Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Archives of Biochemistry and Biophysics, 311, 437-442.
11. CHANG, T. K. H., WEBER, G. F., CRESPI, C. L. and WAXMAN, D. J., 1993, Differential activation of cyclophosphamide and iphosphamide by cytochromes P450 2B and 3A in human liver miscosomes. Cancer Research, 53, 5629-5637.
12. CHANG, Y.-T., STIFFELMAN, P. B., VASKER, I. A., LOEW, G. H., BRIDGES, A. and WASKELL, L., 1997, Construction of a 3D model of cytochrome P4502B4. Protein Engineering, 10, 119-129.
13. CODE, E. L., CASPI, C. L., PENMAN, B. W., GONZALEZ, F. J., CHANG, T. K. H. and WAXMAN, D. J., 1997, Human cytochrome P4502B6: interindividual hepatic expression, substrate specificity and role in procarcinogen activation. Drug Metabolism and Disposition, 25, 985-993.
14. DE LEMOS-CHIARANDINI, C., FREY, A. B., SABATINI, D. D. and KREIBACH, G., 1987, Determination of the membrane topology of the phenobarbital-inducible rat liver cytochrome P450 isozyme PB-4 using site-specific antibodies. Journal of Cell Biology, 104, 209-219.
15. DEHAL, S. S. and KUPFER, D., 1994, Metabolism of the proestrogenic pesticide methoxychlor by hepatic P450 monooxygenases in rats and humans. Drug Metabolism and Disposition, 22, 937-946.
16. DELUCA, J. G., DYSART, G. R., RASNICK, D. and BRADLEY, M. O., 1988, A direct, highly sensitive assay for cytochrome P450 catalysed O-deethylation using a novel coumarin analog. Biochemical Pharmacology, 37, 1731-1739.
17. EKINS, S., VANDENBRANDEN, M., GILLESPIE, J. S., RING, B. J., WRIGHTON, S. A. and WIXEL, J. H., 1997, A preliminary substrate pharmacophore for CYP2B6. In Proceedings of the 8th ISSX North American Meeting, South Carolina, 6-30 October, 1997, vol. 12, p. 63.
18. EKINS, S., VANDENBRANDEN, M., RING, B. J. and WRIGHTON, S. A., 1996, Kinetic and inhibition characteristics on CYP2B6. In ISSX Proceedings, 7th North American ISSX Meeting, San Diego, 20-25 October, vol. 10, p. 232.
19. ELDIRDIRI, N., 1992, Uptake and metabolic effects of some halogenoalkanes, PhD thesis, University of Surrey, Guildford.
20. ENGEL, G., HOFMAN, U., HEIDEMAN, H., COSME, J. and EICHELBAUM, M., 1996, Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxyantipyrine and 4-norantipyrine. Clinical Pharmacology and Therapeutics, 59, 613-623.
21. 5. Archives of Biochemistry and Biophysics, 271, 424-432.
22. Funae, Y. and Imaoka, S., 1993, Cytochrome P450 in rodents. In J. B. Schenkman and H. Griem (eds) Cytochrome P450 (Berlin: Springer), pp. 221-238.
23. GIBSON, G. G. and SKETT, P., 1994, An Introduction to Drug Metabolism (London: Chapman & Hall).
24. GOLLY, I. and HLAVICA, P., 1992, Chemical modification of lysine residues in cytochrome P450LM2 (P450IIB4): influence on heme liganding of arylamines. Archives of Biochemistry and Biophysics, 292, 287-294.
25. GONZALEZ, F. J., 1992, Human cytochromes P450: problems and prospects. Trends in Biochemical Sciences, 13, 346-352.
26. GONZALEZ, F. J. and GELBOIN, H. V., 1994, Role of human cytochromes P450 in the metabolism activation of chemical carcinogens and toxins. Drug Metabolism Reviews, 26, 165-183.
27. GONZALEZ, F. J. and LEE, Y. H., 1996, Constitutive expression of hepatic cytochrome P450 genes. FASEB Journal, 10, 1112-1117.
28. GOTOH, O., 1992, Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. Journal of Biological Chemistry, 267, 83-90.
29. GRIMM, S. W., DYROFF, M. C., PHILPOT, R. M. and HALPERT, J. R., 1994, Catalytic selectivity and mechanism-based inactivation of stably expressed and hepatic cytochromes P450 2B4 and 2B5: implications of the cytochrome P450 2B5 polymorphism. Molecular Pharmacoogy, 46, 1090-1099.
30. GUENGERICH, F. P., 1995, Human cytochrome P450 enzymes. In P. R. Ortiz de Montellano (ed.), Cytochrome P450 (New York: Plenum), pp. 473-535.
31. HALPERT, J. R., 1995, Structural basis of selective cytochrome P450 inhibition. Annual Review of Pharmacology and Toxicology, 35, 29-53.
32. HALPERT, J. R. and HE, Y., 1993, Engineering of cytochrome P450 2B1 specificity. Journal of Biological Chemistry, 268, 4453-4457.
33. HARLOW, G. R. and HALPERT, J. R., 1996, Mutagenesis study of Asp-290 in cytochrome P4502B11 using a fusion protein with rat NADPH-cytochrome P450 reductase. Archives of Biochemistry and Biophysics, 326, 85-92.
34. HARLOW, G. R., HE, Y. A. and HALPERT, J. R., 1997, Functional interaction between amino acid residues 242 and 290 in cytochromes P450 2B1 and 2B11. Biochimica et Biophysica Acta, 1338, 259-266.
35. HASLER, J. A., HARLOW, G. R., SZKLARZ, G. D., JOHN, G. H., KEDZIE, K. M., BURNETT, V. L., HE, Y.-A., KAMINSKY, L. S. and HALPERT, J. R., 1994, Site-directed mutagenesis of putative substrate recognition sites in cytochrome P450 2B11: importance of amino acid residues 114, 290 and 363 for substrate specificity. Molecular Pharmacology, 46, 338-345.
36. HE, Y., LUO, Z., KLEKOTKA, P. A., BURNETT, V. L. and HALPERT, J. R., 1994, Structural determinants of cytochrome P450 2B1 specificity: evidence for five substrate recognition sites. Biochemistry, 33, 4419-4424.
37. HE, Y.-A., BALFOUR, C.A., KEDZIE, K. M. and HALPERT, J. R., 1992, Role of residue 478 as a determinant of the substrate specificity of cytochrome P4502B1. Biochemistry, 31, 9220-9226.
38. HE, Y. Q., HE, Y.-A. and HALPERT, J. R., 1995, Escherichia coli expression of site-directed mutants of cytochrome P4502B1 from six substrate recognition sites: substrate specificity and inhibitor selectivity studies. Chemical Research in Toxicology, 8, 574-579.
39. HEYN, H., WHITE, R. B. and STEVENS, J. C., 1996, Catalytic role of cytochrome P4502B6 in N-demethylation of S-mephenytoin. Drug Metabolism and Disposition, 24, 948-954.
40. INGELMAN-SUNDBERG, M., 1986, Cytochrome P-450 organization and membrane interactions. In P. R. Ortiz de Montellano (ed.), Cytochrome P450 (New York: Plenum), pp. 119-160.
41. JANSSON, I., CURTI, M., EPSTEIN, P. M., PETERSON, J. A. and SCHENKMAN, J. B., 1990, Relationship between phosphorylation and cytochrome P450 destruction. Archives of Biochemistry and Biophysics, 283, 285-292.
42. JOHNSON, E. F., 1992, Mapping determinants of the substrate selectivities of P450 enzymes by site-directed mutagenesis. Trends in Pharmaceutical Sciences, 13, 122-126.
43. JONES, B. C., HAWKSWORTH, G., HORNE, V. A., NEWLANDS, A., MORSMAN, J., TUTE, M. S. and SMITH, D. A., 1996, Putative active site template model for cytochrome P4502C9 (tolubtamide hydroxylase). Drug Metabolism and Disposition, 24, 260-266.
44. KAMATAKI, T., 1993, Metabolism of xenobiotics. In T. Omura, Y. Ishimura and Y. Fujii-Kuriyama (eds), Cytochrome P450 (Tokyo: Kodansha), pp. 141-158.
45. KEDZIE, K. M., BALFOUR, C. A., ESCOBAR, G. Y., GRIMM, S. W., HE, Y., PEPPERL, D. J., REGAN, J. W., STEVENS, J. C. and HALPERT, J. R., 1991, Molecular basis for a functionally unique cytochrome P450IIB1 variant. Journal of Biological Chemistry, 266, 22515-22521.
46. KOLESANOVA, E. F., KOZIN, S. A., LEMESHKO, A. O. and ARCHAKOV, A. I., 1994, Epitope mapping of cytochrome P450 2B4 by peptide scanning. Biochemistry and Molecular Biology International, 32, 465-473.
47. LAKE, B. G., 1987, Preparation and characterisation of microsomal fractions for studies of xenobiotic metabolism. In K. Snell and B. Mullock (eds), Biochemical Toxicology: A Practical Approach (Oxford: IRL), pp. 183-215.
48. bm3). Xenobiotica, 25, 333-366.
49. LEWIS, D. F. V., 1996, Cytochromes P450: Structure, Function and Mechanism (London: Taylor & Francis).
50. LEWIS, D. F. V. and LAKE, B. G., 1997, Molecular modelling of mammalian CYP2B isoforms and their interaction with substrates, inhibitors and redox partners. Xenobiotica, 27, 443-478.
51. LEWIS, D. F. V., EDDERSHAW, P. J., DICKINS, M., TARBIT, M. H. and GOLDFARB, P. S., 1998a, Structural determinants of cytochrome P450 substrate specificity, binding affinity and catalytic rate. Chemico-Biological Interactions 115, 175-199.
52. LEWIS, D. F. V., IOANNIDES, C. and PARKS, D. V., 1998b, An improved and updated version of the COMPACT procedure for the evaluation of P450-mediated chemical activation. Drug Metabolism Reviews, 30, 709-737.
53. LEWIS, D. F. V., IOANNIDES, C. and PARKE, D. V., 1995b, A quantitative structure-activity relationship study on a series of 10 para-substituted toluenes binding to cytochrome P4502B4 (CYP2B4) and also their hydroxylation rates. Biochemical Pharmacology, 50, 619-625.
54. LEWIS, D. F. V., LAKE, B. G. and PARKE, D. V., 1995a, Molecular orbital-generated QSARs in an homologous series of alkoxy resorufins and studies of their interactive docking with cytochromes P450. Xenobiotica, 25, 1355-1369.
55. LI, H. and POULOS, T. L., 1997, The structure of the cytochrome P450BM-3 haem domain complexed with the fatty acid substrate, palmitoleic acid. Nature Structural Biology, 4, 140-146.
56. MILLER, J. P., HERBETTE, L. G. and WHITE, R. E., 1996, X-ray diffraction analysis of cytochrome P450 2B4 reconstituted into liposomes. Biochemistry, 35, 1466-1474.
57. MIMURA, M., BABA, T., YAMAZAKI, Y., OHMORI, S., INUI, Y., GONZALEZ, F. J., GUENGERICH, F. P. and SHIMADA, T., 1993, Characterization of cytochrome P450 2B6 in human liver microsomes. Drug Metabolism and Disposition, 21, 1046-1056.
58. MODI, S., SUTCLIFFE, M. J., PRIMROSE, W. U., LIAN, L.-Y. and ROBERTS, G. C. K., 1996, The catalytic mechanism of cytochrome P450 BM3 involves a 6 Å movement of the bound substrate on reduction. Nature Structural Biology, 3, 414-417.
59. NEDECHEVA, V. and GUT, I., 1994, P450 in the rat and man: methods of investigation, substrate specificities and relevance to cancer. Xenobiotica, 24, 1151-1175.
60. NELSON, D. R., KOYMANS, L., KAMATAKI, T., STEGEMAN, J. J., FEYEREISEN, R., WAXMAN, D. J., WATERMAN, M. R., GOTOH, O., COON, M. J., ESTABROOK, R. W., GUNSALUS, I. C. and NEBERT, D. W., 1996, P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics, 6, 1-42.
61. NIMS, R. W. and LUBET, R. A., 1996, The Cyp2b subfamily. In C. Ioannides (ed.), Cytochromes P450 - Metabolic and Toxicological Aspects (Boca Raton: CRC Press), pp. 135-160.
62. b(e). Archives of Biochemistry and Biophysics, 287, 105-111.
63. OKEY, A. B., 1990, Enzyme induction in the cytochrome P450 system. Pharmacology and Therapeutics, 45, 241-298.
64. 5. Biochemical and Biophysical Research Communications, 201, 1090-1095.
65. ONO, S., HATANAKA, T., MIYZAWA, S., TSUTSUI, M., AOYAMA, T., GONZALEZ, F. J. and SATO, T., 1996, Human liver microsomal diazepam metabolism using cDNA-expressed cytochrome P450s: role of CYP2B6, 2C 19 and 3A subfamily. Xenobiotica, 26, 1155-1166.
66. PETZOLD, D. R., REIN, H., SCHWARZ, D., SOMMER, M. and RUCKPAUL, K., 1985, Relation between the structure of benzphetamine analogues and their binding properties to cytochrome P450LM2. Biochimica et Biophysica Acta, 829, 253-261.
67. RAVICHANDRAN, K. G., BODDUPALLI, S. S., HASEMANN, C. A., PETERSON, J. A. and DEISENHOFER, J., 1993, Crystal structure of the hemoprotein domain of cytochrome P450BM-3, a prototype for microsomal P450s. Science, 261, 731-736.
68. REIDY, G. F., MEHTA, I. and MURRAY, M., 1993, Inhibition of oxidative drug metabolism by orphenadrine: in vitro and in vivo evidence for isozyme-specific complexation of cytochrome P450 and inhibition kinetics. Molecular Pharmacology, 35, 736-743.
69. RENDIC, S. and DI CARLO, F. J., 1997, Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers and inhibitors. Drug Metabolism Reviews, 29, 413-580.
70. ROFFEY, S. J., 1993, Structure-activity relationships in the metabolism of a series of tertiary amines by cytochrome P450. PhD thesis, University of Surrey, Guildford.
71. ROSSI, M., MARKOVITZ, S. and CALLAHAN, T., 1987, Defining the active site of cytochrome P450: the crystal and molecular structure of an inhibitor, SKF-525A. Carcinogenesis, 8, 881-887.
72. RUCKPAUL, K., REIN, H. and BLANCK, J., 1989, Regulation mechanisms of the activity of the hepatic endoplasmic cytochrome P450. Frontiers in Biotransformation, 1, 1-65.
73. RUZICKA, J. A. and RUENITZ, P.C., 1992, Cytochrome P450-mediated N-dechloroethylation of cyclophosphamide and ifosfamide in the rat. Drug Metabolism and Disposition, 20, 770-772.
74. SCHENKMAN, J. B., 1992, Steroid metabolism by constitutive cytochromes P450. Journal of Steroid Biochemistry and Molecular Biology, 43, 1023-1030.
75. SCHULZE, J., LEHNERER, M., LEWIS, D. F. V. and HLAVICA, P., 1998, Amino acid residue Glu-250 has a functional role in the assembly of rabbit liver microsomal cytochrome P450 2B4 (CYP2B4). Biochemistry and Molecular Biology International, 44, 1147-1155.
76. SCHWARZE, W., BLANCK, J., RISTAU, O., JANIG, G. R., POMMERENING, K., REIN, H. and RUCKPAUL, K., 1985, Spin state control of cytochrome P450 reduction and catalytic activity in a reconstituted P450LM2 system as induced by a series of benzphetamine analogues. Chemico-Biological Interactions, 54, 127-141.
77. SHIMADA, T., MIMURA, M., INOUE, K., NAKAMURA, S.-I., ODA, H., OHMORI, S. and YAMAZAKI, H., 1997, Cytochrome P450-dependent drug oxidation activities in liver microsomes of various animal species including rats, guinea pigs, dogs, monkeys and humans. Archives of Toxicology, 71, 401-408.
78. 5. Methods in Enzymology, 206, 31-49.
79. SMITH, D. A., ACKLAND, M. J. and JONES, B. C., 1997, Properties of cytochrome P450 isoenzymes and their substrates. Part 1: Active site characteristics. Drug Discovery Today, 2, 406-414.
80. SOUCEK, P. and GUT, I., 1992, Cytochromes P450 in rats: structures, functions, properties and relevant human forms. Xenobiotica, 22, 83-103.
81. cam binding surface as defined by site-directed mutagenesis and electrostatic modeling. Biochemistry, 29, 7381-7386.
82. cam electron transfer complex. Biochemistry, 28, 8201-8205.
83. 3H] methoxychlor as a probe for liver microsomal CYP2B activity. A potential assay for CYP2B in vivo. ISSX Proceedings, 4th International Meeting, Seattle, 27-31 August, vol. 8, p. 66.
84. SWANSON, B. A., DUTTON, D. R., LUNETTA, J. M., YANG, C. S. and ORTIZ DE MONTELLANO, P. R., 1991, The active sites of cytochromes P450IA1, and IIB1, IIB2 and IIE1. Journal of Biological Chemistry, 266, 19258-19264.
85. SWANSON, B. A., HALPERT, J. R., BORNHEIM, L. M. and ORTIZ DE MONTELLANO, P. R., 1992, Topological analysis of the active sites of cytochrome P450IIB4 (rabbit), P450IIB10 (mouse) and P450IIB11 (dog) by in situ rearrangement of phenyl-iron complexes. Archives of Biochemistry and Biophysics, 292, 42-46.
86. SZCZESNA-SKORUPA, E. and KEMPER, B., 1993, An N-terminal glycosylation signal on cytochrome P450 is restricted to the endoplasmic reticulum in a luminal orientation. Journal of Biological Chemistry, 268, 1757-1762.
87. SZKLARZ, G. D., HE, Y. Q., KEDZIE, K. M., HALPERT, J. R. and BURNETT, V. L., 1996, Elucidation of amino acid residues critical for unique activities of rabbit cytochrome P450 2B5 using hybrid enzymes and reciprocal site-directed mutagenesis with rabbit cytochrome P450 2B4. Archives of Biochemistry and Biophysics, 327, 308-318.
88. SZKLARZ, G. D., HE, Y. A. and HALPERT, J. R., 1995, Site-directed mutagenesis as a tool for molecular modeling of cytochrome P450 2B1. Biochemistry, 34, 14312-14322.
89. TESTA, B., 1988, Substrate and product stereoselectivity in monooxygenase-mediated drug activation and inactivation. Biochemical Pharmacology, 37, 85-92.
90. TESTA, B. and JENNER, P., 1981, Inhibitors of cytochrome P-450s and their mechanism of action. Drug Metabolism Reviews, 12, 1-117.
91. 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 aryl-iron complexes. Biochemistry, 31, 6911-6916.
92. BMS). Journal of Biological Chemistry, 267, 5614-5620.
93. UVAROV, V. U., SOTNICHENKO, A. I., VODOVOZOVA, E. L., MOLOTKOVSKY, J. G., KOLESANOVA, E. F., LYULIKIN, Y. A., STIER, A., KRUEGER, V. and ARCHAKOV, A.I., 1994, Determination of membrane-bound fragments of cytochrome P4502B4. European Journal of Biochemistry, 222, 483-489.
94. VAZ, A. D. N., PERNECKY, S. J., RANER, G. M. and COON, M. J., 1996, Peroxo-iron and oxenoid-iron species as alternative oxygenating agents in cytochrome P450-catalyzed reactions: switching by threonine-302 to alanine mutagenesis of cytochrome P450 2B4. Proceedings of the National Academy of Sciences, USA, 93, 4644-4648.
95. 2 and their partitioning into liposomal membranes. Biochemical Journal, 284, 483-490.
96. VON WACHENFELDT, C. and JOHNSON, E. F., 1995, Structures of eukaryotic cytochrome P450 enzymes. In P. R. Ortiz de Montellano (ed.), Cytochrome P450 (New York: Plenum), pp. 183-223.
97. WANG, M., ROBERTS, D. L., PASCHKE, R., SHEA, T. M., MASTERS, B. S. S. and KIM, J.-J. P., 1997, Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes. Proceedings of the National Academy of Sciences, USA, 94, 8411-8416.
98. WAXMAN, D. J., 1988, Interactions of hepatic cytochromes P450 with steroid hormones. Biochemical Pharmacology, 37, 71-84.
99. WAXMAN, D. J. and AZAROFF, L., 1992, Phenobarbital induction of cytochrome P450 gene expression. Biochemical Journal, 281, 577-592.
100. WAXMAN, D. J., DANNAN, G. A. and GUENGERICH, F. P., 1985, Regulation of rat hepatic cytochrome P450: age-dependent expression, hormonal imprinting and xenobiotic inducibility of sex-specific isoenzymes. Biochemistry, 24, 4409-4417.
101. WELCH, R. M., LAI, A. A. and SCHROEDER, D. M., 1987, Pharmacological significance of the species differences in bupropion metabolism. Xenobiotica, 17, 287-298.
102. WHITE, R. E. and MCCARTHY, M. B., 1986, Active site mechanics of liver microsomal cytochrome P450. Archives of Biochemistry and Biophysics, 246, 19-32.
103. WHITLOCK, J. P. and DENISON, M. S., 1995, Induction of cytochrome P450 enzymes that metabolize xenobiotics. In P. R. Ortiz de Montellano (ed.), Cytochrome P450 (New York: Plenum), pp. 367-390.
104. WURM, R. M., DUNN, J. A., SILVER, I. S. and PATEL, D. K., 1996, In vitro metabolism of bupropion by human liver microsomes and cDNA expressed human cytochrome P450s. In ISSX Proceedings, 7th North American Meeting, San Diego, 20-25 October, vol. 10, p. 371.
105. YAO, K., FALICK, A. M., PATEL, N. and CORREIA, M. A., 1993, Cumene hydroperoxide-mediated inactivation of cytochrome P4502B1. Journal of Biological Chemistry, 268, 59-65.
106. ZIMNIAK, P. and WAXMAN, D. J., 1993, Liver cytochrome P450 metabolism of endogenous steroid hormones, bile acids and fatty acids. In J. B. Schenkman and H. Griem (eds), Cytochrome P450 (Berlin: Springer), pp. 123-144.