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Xenobiotica
the fate of foreign compounds in biological systems
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Research Article

Molecular modelling of mammalian CYP2B isoforms and their interaction with substrates, inhibitors and redox partners

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Pages 443-478 | Published online: 22 Sep 2008

References

  • ALEXANDER, D. M., MATHEW, G. E. A. and WILSON, B. J., 1985, Metabolism of phenylbutazone in rats. Xenobiotka, 15, 123–128.
  • 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 P-45011BI catalytic activity. Journal of Biological Chemistry, 264, 21327–21333.
  • BERNHARDT, R., 1993, Chemical probes of cytochrome P450 structure. In Cytochrome P450, edited by J. B. Schenkman and H. Griem (Berlin: Springer), pp. 547–560.
  • BERNHARDT, R., 1995, Cytochrome P450: structure, function, and generation of reactive oxygen species. Reviews of Physiology, Biochemistry and Pharmacology, 127, 137–221.
  • BERNHARDT, R., KRAFT, R., OTTO, A. and RUCKPAUL, K. 1988, Electrostatic interactions between cytochrome P450 LM2 and NADPH-cytochrome P450 reductase. Biomedica et Biophysica Acta, 47, 581–592.
  • BERNHARDT, R., KRAFT, R. and RUCKPAUL, K., 1989a, Molecular mechanism of P-450/reductase interaction. In Cytochrome P-450: Biochemistry and Biophysics, edited by I. Schuster (London: Taylor & Francis), pp. 320–323.
  • BERNHARDT, R., MAKOWER, A., JÄNIG, G.-R. and RUCKPAUL, K., 1984, Selective chemical modification of a functionally linked lysine in cytochrome P-450 LM2. Biochimica et Biophyska Acta, 785, 186–190.
  • BERNHARDT, R., ST1EL, H. and RUCKPAUL, K., 1989b, Distance between lysine 384 and haem of cytochrome P-450 LM2 (P-450I1B4) studied by fluorescence energy transfer measurements. Biochemical and Biophysical Research Communications, 163, 1282–1289.
  • BERRY, D. J., WEDLEY, M., GRAHAME, R., GOULDING, R., GAETANI, M. and PARKE, D. V., 1993, Pharmacokinetics of single oral doses of feprazone in patients with rheumatoid arthritis or with impaired renal clearance. Xenobiotka, 23, 1231–1240.
  • BLANCK J., REIN, H., SOMMER, M., RISTAU, 0., SMETTAN, G. and RUCKPAUL, K., 1983, Correlations between spin equilibrium shift, reduction rate, and N-demethylation activity in liver microsomal cytochrome P-450 and a series of benzphetamine analogues as substrates, as Biochemical Pharmacology, 32, 1683–1688.
  • BORES, G. F. and CRAVEDI, J.-P., 1994, Metabolism of chloramphenicol: a story of nearly 50 years. Drug Metabolism Reviews, 26, 767–783.
  • BUENING, M. K. and FRANKLIN, M. R., 1976, SKF-525A inhibition, induction, and 452 nm complex formation. Drug Metabolism and Disposition, 4, 244–255.
  • BURKE, M. D., THOMPSON S ELCOMBE, C. R., HALPERT, J., HAAPARANTA, T. and MAYER, R. T., 1985, Ethoxy-, pentoxy- and benzyloxy phenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P450. Biochemical Pharmacology, 34, 3337–3345.
  • CLARK, M., CRAMER, R. D. and VAN OPDENBOSCH, N., 1989, Validation of the general purpose Tripos 5.2 force field. Journal of Computational Chemistry, 10, 982–1012.
  • CUPP -VICKERY, J. R. and PouLos, T. L., 1995, Structure of cytochrome P450„,„ involved in erythromycin biosynthesis. Structural Biology, 2, 144–155.
  • DE LEMOS -CHIARANDINI, C., FREY, A. B., SABATINI, D. D. and KREIBICH, G., 1987, Determination of the membrane topology of the phenobarbital-inducible rat liver cytochrome P-450 isoenzyme PB-4 using site-specific antibodies. Journal of Cell Biology, 104, 209–219.
  • DEGTYARENKO, K. N. and ARCHAKOV, A. I., 1993, Molecular evolution of P450 superfamily and P450-containing monoxygenase systems. FEBS Letters, 332, 1–8.
  • 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. ELDIRDIRI, N., 1992, Uptake and metabolic effects of some halogenoalkanes. PhD thesis, University of Surrey.
  • EPSTEIN, P. M., CURTI, M., JANSSON, I., HUANG, C.-K. and SCHENICMAN, J. B., 1989, Phosphorylation of cytochrome P450: regulation by cytochrome b5. Archives of Biochemistry and Biophysics, 271, 424–432.
  • FAWCETT, S. C ., KING, L. J., BUNYAN, P. J. and STANLEY, P. I., 1987, The metabolism of '4C-DDT, C-DDD, 14 C-DDE and 14 C-DDMU in rats and Japanese quail. Xenobiotka, 17, 525–538. GIBSON, G. G. and TAMBURINI, P. P., 1984, Cytochrome P-450 spin state: inorganic biochemistry of haem iron ligation and functional significance. Xenobiotka, 14, 27–47.
  • GONZALEZ, F. J. and GELBOIN, H. V., 1994, Roles of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. Drug Metabolism Reviews, 26, 165–183.
  • GOTOH, 0., 1992, Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analysis of amino acid and coding nucleotide sequences. Journal of Biological Chemistry, 267, 83–90.
  • GRAHAM -LORENCE, S. and PETERSON, J. A., 1996, P450s : structural similarities and functional differences. F ASEB Journal, 10, 206–214.
  • HALPERT, J. R., 1995, Structural basis of selective cytochrome P450 inhibition. Annual Reviews of Pharmacology and Toxicology, 25, 29–53.
  • HALPERT, J. R., GUENGERICH, F. P., BEND, J. R. and CORREIA, M. A. 1994, Selective inhibitors of cytochromes P450. Toxicology and Applied Pharmacology, 125, 163–175.
  • HALPERT, J. R. and HE, Y., 1993, Engineering of cytochrome P450 2B1 specificity. Journal of Biological Chemistry, 268, 4453–4457.
  • HALPERT, J. R., HE, Y., S ZKLARZ, G. D., HE, Y., HASLER, J. A., BURNETT, V. L., HARLOW, G. R., KLETOTKA, P. A. and JOHN, G. H., 1995, Alteration of cytochrome P450 substrate specificity by site-directed mutagenesis: application to drug metabolism studies. In Proceedings of the 4th ISSX Meeting, Seattle, Washington, 27–31 August 1995, p. 41.
  • HALPERT, J. R., MILLER, N. E. and GORSKY, L. D., 1985, On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. Journal of Biological Chemistry, 260, 8397–8403.
  • HAMMOND, D. K., BJERCKE, R. J., LANGONE, J. J. and STROBEL, H. W., 1991, Metabolism of nicotine by rat liver cytochromes P-450. Drug Metabolism and Disposition, 19, 804–808.
  • HASEMANN, C. A., KURUMBAIL, R. G., BODDUPALLI, S. S., PETERSON, J. A. and DEISENHOFER, J., 1995, Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure, 3, 41–62.
  • HASLER, J. A., HARLOW, G. R., SZKLARZ, G. F., JOHN, G. H., KEDZ1E, 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 cyothcrome P450 2B11: importance of amino acid residues 114, 290 and 363 for substrate specificity. Molecular Pharmacology, 46, 338–345.
  • HE, Y., BALFOUR, C. A., KEDZIE, K. M. and HALPERT, J. R., 1992, Role of residue 478 as a determinant of the substrate specificity of cytochrome P450 2B1. Biochemistry, 31, 9220–9226.
  • 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.
  • IBEANU, G. C., GHANAYEM, B. I., LINKO, P., LI, L., PEDERSEN, L. G. and GOLDSTEIN, J. A., 1996, Identification of residues 99, 220 and 221 of human cytochrome P4502C19 as key determinants of omeprazole hydroxylase activity. Journal of Biological Chemistry, 271, 12496–12501.
  • INOUYE, K. and CooN, M. J., 1985, Properties of the tryptophan residue in rabbit liver microsomal cytochrome P-450 isozyme 2 as determined by fluorescence. Biochemical and Biophysical Research Communications, 128, 676–682.
  • JANSSON, I., 1993, Post translational modification of cytochrome P450. In Cytochrome P450, edited by J. B. Schenkman and H. Grien (Berlin: Springer), pp. 561–580.
  • 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.
  • JEFCOME, C. R. E., GAYLOR, J. L. and CALABRESE, R. L. 1969, Ligand interactions with cytochrome P-450. I. Binding of primary amines. Biochemistry, 8, 3455–3463.
  • JOHNSON, E. F., 1992, Mapping determinants of the substrate selectivities of P450 enzymes by site-directed mutagenesis. Trends in Pharmaceutical Sciences, 13, 122–126.
  • KAMINSKY, L. S., KENNEDY, M. W., ADAMS, S. M. and GUENGERICH, F. P., 1981, Metabolism of dichlorobiphenyls by highly purified isozymes of rat liver cytochrome P-450. Biochemistry, 20, 7379–7384.
  • 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.
  • KENNEDY, M. W., CARPENTIER, N. K., DYMERSKI, P. P. and KAMINSKY, L. S., 1981, Metabolism of dichlorobiphenyls by hepatic microsomal cytochrome P-450. Biochemical Pharmacology, 30, 577–588.
  • KING, C. M., 1995, Tamoxifen and the induction of cancer. Carcinogenesis, 16, 1449-1454. KOLESANOVA, E. F., KOZIN, S. A., LEMESHKO, A. 0. and ARCHAKOV, A. I., 1994, Epitope mapping of cytochrome P450 2B4 by peptide scanning. Biochemistry and Molecular Biology International, 32, 465–473.
  • LAKE, B. G. and LEWIS, D. F. V., 1996, The CYP4 family. In Cytochromes P450: Metabolic and Toxicological Aspects, edited by C. Ioannides (Boca Raton: CRC Press) pp. 269–295.
  • LEVIN, S. S., VARS, H. M., SCHLEYER, H. and COOPER, D. Y., 1986. The metabolism and excretion of enzyme-inducing doses of phenobarbital by rats with bile fistulas. Xenobiotka, 16, 213-224. LEWIS, D. F. V., 1995, Three-dimensional models of human and other mammalian P450s constructed from an alignment with P450102 (P450b,n3). Xenobiotka, 25, 333–366.
  • LEWIS, D. F. V., 1996a, Cytochromes P450: Structure, Function and Mechanism. (London: Taylor and Francis).
  • LEWIS, D. F. V., 1996b, Quantitative structure-activity relationships in substrates, inducers and inhibitors of cytochrome P4501 (CYP1). Drug Metabolism Reviews (in press).
  • LEWIS, D. F. V., 1996c, Molecular orbital calculations on primary aliphatic amines: Correlations with binding to cytochrome P4502B4 (CYP2B4) and quantitative structure—activity relationships. Biochemical Pharmacology (submitted).
  • LEWIS, D. F. V., EDDERSHAW, P. J., GooLFARB, P. S. and TARBIT, M. H., 1996, Molecular modelling of CYP3A4 from an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotka, 26, 1067–1086.
  • LEWIS, D. F. V., IOANNIDES, C. and PARKE, D. V., 1987, Structural requirements for substrates of cytochromes P-450 and P-448. Chemko-Biological Interactions, 64, 39–60.
  • 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 their hydroxylation rates. Biochemical Pharmacology, 50, 619–625.
  • LEWIS, D. F. V. and LAKE, B. G., 1995, Molecular modelling of members of the P4502A subfamily: application to studies of enzyme specificity. Xenobiotka, 25, 585–598.
  • LEWIS, D. F. V. and LAKE, B. G., 1996, Molecular modelling of the CYP1A subfamily members based on an alignment with CYP102: rationalization of CYP1A substrate specificity in terms of active site amino acid residues. Xenobiotka, 26, 723–753.
  • LEWIS, D. F. V., LAKE, B. G. and PARKE, D. V., 1995a, Molecular orbital-generated QSARs in an homologous series of alkoxyresorufins and studies of their interactive docking with cytochromes P450. Xenobiotka, 25, 1355–1369.
  • LEWIS, D. F. V. and MOEREELS, H., 1992, The sequence homologies of cytochromes P-450 and active site geometries. Journal of Computer-Aided Molecular Design, 6, 235–252.
  • LEWIS, D. F. V., TAMBURINI, P. P. and GIBSON, G. G., 1986, The interaction of a homologous series of hydrocarbons with hepatic cytochrome P-450. Molecular orbital-derived electronic and structural parameters influencing the haemoprotein spin-state. C hemico-Biological Interactions, 58, 289–299.
  • LUNETTA J. M., SUGIYAMA, K. and CORREIA, M. A., 1989, Secobarbital-mediated inactivation of rat liver cytochrome P-450b : a mechanistic reappraisal. Molecular Pharmacology, 35, 10–17.
  • MANI, C., GELBOIN, H. V., PARK, S. S., PEARCE, R., PARKINSON, A. and KUPFER, D., 1993, Metabolism of the antimammary cancer antiestrogenic agent tamoxifen. Drug Metabolism and Disposition, 21, 645–656.
  • MILLER, J. P. AND HALPERT, J. R., 1986, Analogues of chloramphenicol as mechanism-based inactivators of rat liver cytochrome P-450: modifications of the propanediol side chain, the p-nitro group, and the dichloromethyl moiety. Molecular Pharmacology, 29, 391–398.
  • 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.
  • MURRAY, M., 1992, P450 enzymes: inhibition mechanisms, genetic regulation and effects of liver disease. Clinical Pharmacokinetics, 23, 132–146.
  • MURRAY, M. and REIDY, G. F., 1990, Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents. Pharmacological Reviews, 42, 85–101.
  • NAU, H., SPIELMAN, Lo TURCO MORLET, C. M., WINCKLER, K., RIEDEL, L. and OBE, G., 1982, Mutagenic, teratogenic and pharmacokinetic properties of cyclophosphamide and some of its deuterated derivatives. Mutation Research, 95, 105–118.
  • NEDELCHEVA, V. and GUT, I., 1994, P450 in the rat and man: methods of investigation, substrate specificities and relevance to cancer. Xenobiotica, 24, 1151–1175.
  • NEGISHI, M., IWASAKI, M., JUVONEN, R. 0., SUEYOSHI, T., DARDEN, T. A. and PEDERSEN, L. G., 1996, Structural flexibility and functional versatility of cytochrome P450 and rapid evolution. Mutation Research, 350, 43–50.
  • NELSON, D. R., KOYMANS, L., KAMATAKI, T., STEGEMAN J. J., FEYEREISEN, R., WAXMAN, D. J., WATERmAN, M. R., GOTOH, 0., 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.
  • ORTIZ DE MONTELLANO, P. R., 1987, Control of the catalytic activity of prosthetic haem by the structure of hemoproteins. Accounts of Chemical Research, 20, 289–294.
  • ORTIZ DE MONTELLANO, P. R., CHAN, W. K., TUCK, S. F., KAIKUS, R. M., BASS, N. M. and PETERSON, J. A., 1992, Mechanism-based probes of the topology and function of fatty acid hydroxylases. FASEB Journal, 6, 695–699.
  • ORTIZ DE MONTELLANO, P. R. and CORREIA, M. A., 1995, Inhibition of cytochrome P450 enzymes. In Cytochrome P450, edited by P. R. Ortiz de Montellano (New York: Plenum), pp. 305-364. PETERSON, L. A., TREVOR, A. and CASTAGNOLI, N., 1987, StereochemipJ studies on the cytochrome P-450 catalyzed oxidation of (s)-nicotine to the (s)-nicotine(5 ) iminium species. Journal ofMedicinal Chemistry, 30, 249–254.
  • 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 P-450 LM2. Biochimica et Biophyska Acta, 829, 253–261.
  • POET, T. S., BRENDEL, K. and HALPERT, J. R., 1994, Inactivation of cytochromes P450 2B protects against cocaine-mediated toxicity in rat liver slices. Toxicology and Applied Pharmacology, 126, 26–32.
  • POON, G. K., CHUI, Y. C., MCCAGUE, R., LONNING, P. E., FENG, R., ROWLANDS, M. G. and JARMAN, M., 1993, Analysis of phase land phase II metabolites of tamoxifen in breast cancer patients. Drug Metabolism and Disposition, 21, 1119–1124.
  • RAVICHANDRAN, K. G., BODDUPALLI, S. S., HASEMAN, C. A., PETERSON, J. A. and DEISENHOFER, J., 1993, Crystal structure of hemoprotein domain of N50„„3, a prototype for microsomal P450s. Science, 261, 731–736.
  • ROFFEY, S. J., 1993, Structure—activity relationships in the metabolism of a series of tertiary amines by cytochrome P450. PhD thesis, University of Surrey.
  • Rossi, M., MARKOVITZ, S. and CALLAHAN, T., 1987, Defining the active site of cytochrome P-450: the crystal and molecular structure of an inhibitor, SKF-525A. Carcinogen esis, 8, 881–887.
  • RUAN, K. H., MILFELD, K., KULMACZ, R. J. and Wu, K. K., 1994, Comparison of the construction of a 3-D model for human thromboxane synthase using P450„n and BM-3 as templates: implications for the substrate binding pocket. Protein Engineering, 7, 1345–1351.
  • RUZICKA, J. A. and RUENITZ, P. C., 1992, Cytochrome P-450-mediated N-dechloroethylation of cyclophosphamide and ifosfamide in the rat. Drug Metabolism and Disposition, 20, 770-772. RYAN, D. E. and LEVIN, W., 1990, Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacology and Therapeutics, 45, 153–239.
  • SCHENICMAN, J. B., SLIGAR, S. G. and CINTI, D. L., 1981, Substrate interaction with cytochrome P-450. Pharmacology and Therapeutics, 12, 43–71.
  • SCHWARZE, W., BLANCK, J., RISTAU, 0., JANIG, G. R., POMMERENING, K., REIN, H. and RUCKPAUL, K., 1985, Spin state control of cytochrome P-450 reduction and catalytic activity in a reconstituted P-450 LM2 system as induced by a series of benzphetamine analogus. Chemko-Biological Interactions, 54, 127–141.
  • SHIMADA, T., YAMAZAKI, H., MIMURA, M., INUI, Y. and GUENGERICH, F. P., 1994, Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 japanese and 30 caucasians. Journal of Pharmacology and Therapeutics, 270, 414–423.
  • SOUCEK, P. and GUT, I., 1992, Cytochromes P-450 in rats: structures, functions, properties and relevant human forms. Xenobiotka, 22, 83–103.
  • SPATZENEGGER, M. and JAEGER, W., 1995, Clinical importance of hepatic cytochrome P450 in drug metabolism. Drug Metabolism Reviews, 27, 397–417.
  • SWANSON, B. A., DUTTON, D. R., LUNETTE, J. M., YANG, C. S. and ORTIZ DE MONTELLANO, P. R., 1991, The active sites of cytochromes P450IA1, IIB1, IIB2 and IIE1. journal of Biological Chemistry, 266, 19258–19264.
  • SZKLARZ, G. D., HE, Y. A. and HALPERT, J. R., 1995, Site-directed mutagenesis as a tool for molecular modeling of cytochrome P4502B1. Biochemistry, 34, 14312–14322.
  • SZKLARZ, G. D., ORNSTEIN, R. L. and HALPERT, J. R., 1994, Application of 3-dimensional homology modelling of cytochrome P4502B1 for interpretation of site-directed mutagenesis results. Journal of Biomolecular Structure and Dynamics, 12, 61–78.
  • TESTA, B. and JENNER, P., 1981, Inhibitors of cytochrome P-450s and their mechanism of action. Drug Metabolism Reviews, 12, 1–117.
  • UVAROV, V. Y., SOTNICHENKO, A. I., YODOVOZOVA, E. L., MALOTKOVSKY, J. G., KOLESANOVA, E. F., LYULKIN, Y. A., STIER, A., KRUEGER, V. and ARCHAKOV, A. I., 1994, Determination of membrane-bound fragments of cytochrome P-450 2B4. European Journal of Biochemistry, 222, 483–489.
  • VON WACHENFELDT, C. and JOHNSON, E. F., 1995, Structures of eukaryotic cytochrome P450 enzymes. In Cytochrome P450, 2nd edn, edited by P. R. Ortiz de Montellano (New York: Plenum), pp. 183–223.
  • WAXMAN, D. J., 1988, Interactions of hepatic cytochromes P450 with steroid hormones. Biochemical Pharmacology, 37, 71–84.
  • WAXMAN, D. J. and AZAROFF, L., 1992, Phenobarbital induction of cytochrome P-450 gene expression. Biochemical Journal, 281, 577–592.
  • WHITE, I. N. H., DAVIES, A., SMITH, L. L., DAWSON, S. and DEMATTEIS, F., 1993, Induction of CYP2B1 and 3A1, and associated monooxygenase activities by tamoxifen and certain analogues in the livers of female rats and mice. Biochemical Pharmacology, 45, 21–30.
  • WHITE, I. N. H., DE MATTEIS, D., GIBBS, A. H., Lim, C. K., WOLF, C. R., HENDERSON, C. and SMITH, L. L., 1995, Species differences in the covalent binding of [14C] tamoxifen to liver microsomes and the forms of cytochrome P450 involved. Biochemical Pharmacology, 49, 1035–1042.
  • WHITE, R. E. and MCCARTHY, M.-B., 1986, Active site mechanics of liver microsomal cytochrome P-450. Archives of Biochemistry and Biophysics, 246, 19–32.
  • WISEMAN, H. and LEWIS, D. F. V., 1996, The metabolism of tamoxifen by human cytochromes P450 is rationalized by molecular modelling of the enzyme—substrate interactions: potential importance to its proposed anticarcinogenic/carcinogenic actions. Carcinogenesis, 17, 1357–1360.
  • Yu, X.-C., SHEN, S. and STROBEL, H. W., 1995, Denaturation of cytochrome P4502B1 by guanidine hydrochloride and urea: evidence for a metastable intermediate state of the active site. Biochemistry, 34, 5511–5517.
  • ZIMNIAK, P. and WAXMAN, D. J., 1993, Liver cytochrome P450 metabolism of endogenous steroid hormones, bile acids and fatty acids. In Cytochrome P450, edited by J. B. Schenkman and H. Griem (Berlin: Springer), pp. 123–144.

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