Quantitative structure-activity relationships (QSARs) within the cytochrome P450 system: QSARs describing substrate binding, inhibition and induction of P450s

Inflammopharmacology

Volumn 11, Issue 1, 2003, Pages 43-73

  Lewis, David F V ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Cytochromes P450; Quantitative structure activity relationships (QSAR); Xenobiotic metabolism

Indexed keywords

CYTOCHROME P450; DEXAMETHASONE; OMEPRAZOLE; TAMOXIFEN;

DRUG MECHANISM; DRUG METABOLISM; ENZYME ACTIVATION; ENZYME BINDING; ENZYME INDUCTION; ENZYME INHIBITION; ENZYME STRUCTURE; ENZYME SUBSTRATE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW; SEQUENCE HOMOLOGY; XENOBIOTIC METABOLISM;

EID: 0037980382     PISSN: 09254692     EISSN: None     Source Type: Journal    
DOI: 10.1163/156856003321547112     Document Type: Review

References (123)

1. Andrews, P. R., Craik, D. J. and Martin, J. L. (1984). Functional group contributions to drug-receptor interactions, J. Med. Chem. 28, 1648-1657.
2. Anzenbacher, P. and Anzenbacherova, E. (2001). Cytochromes P450 and metabolism of xenbiotics, Cell. Mol. Life Sci. 58, 737-747.
3. Ayrton, A. D., McFarlane, M., Walker, R., et al. (1990). The induction of P450 1 proteins by aromatic amines may be related to their carcinogenic potential, Carcinogenesis 4, 803-809.
4. o†k values - possible implications in chemotherapy and biotechnology, Biochem. Pharmacol. 61, 1049-1055.
5. Brown, L. P., Lewis, D. F. V., Orton, T. C., et al. (1989). Teratology of phenylhydantoins in an in vitro system: molecular orbital-generated quantitative structure-activity relationships, Xenobiotica 19, 1471-1481.
6. Brown, S. J., Raja, A. A. and Lewis, D. F. V. (1994). A comparison between COMPACT and HazardExpert evaluations for 80 chemicals tested by the NTP/NCI rodent bioassay, Alt. Lab, Animals 22, 482-500.
7. Cheung, Y.-L., Lewis, D. F. V., Gray, T. J. B., et al. (1997). Diaminonaphthalenes and related amino compounds: mutagenicity, CYP1A induction and interaction with the Ah receptor, Toxicology 118, 115-127.
8. Connolly, M. L. (1983). Solvent-accessible surfaces of proteins and nucleic acids, Science 221, 709-713.
9. Cronin, M. T. D., Manga, N., Seward, J. R., et al. (2001). Parameterization of electrophilicity for the prediction of the toxicity of aromatic compounds, Chem. Res. Toxicol. 14, 1498-1505.
10. Csizmadia, F., Tsantili-Kakoulidou, A., Panderi, I., et al. (1997). Prediction of distribution coefficient from structure. 1. Estimation method, J. Pharm. Sci. 86, 865-871.
11. da Silva, J. J. R. F. and Williams, R. J. P. (1991). The Biological Chemistry of the Elements. Clarendon Press, Oxford.
12. Ekins, S., de Groot, M. J. and Jones, J. P. (2001). Pharmacophore and three-dimensional quantitative structure activity relationship methods for modeling cytochrome P450 active sites, Drug Metab. Dispos. 29, 936-944.
13. Evans, W. E. and Relling, M. V. (1999). Pharmacogenomics: translating functional genomics into rational therapeutics, Science 286, 487-491.
14. Fleming, I. (1980). Frontier Orbitals and Organic Chemical Reactions. Wiley, Chichester.
15. m, Drug Metab. Rev. 28, 513-526.
16. Guengerich, F. P. (2001). Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity, Chem. Res. Toxic. 14, 611-650.
17. Guengerich, F. P. (2002). Cytochrome P450, in: Enzyme Systems that Metabolize Drugs and other Xenobiotics, C. Ioannides (Ed.), Ch. 2, pp. 33-65. Wiley, New York, NY.
18. Hansch, C. (1993). Quantitative structure-activity relationships and the unnamed science, Acc. Chem. Res. 26, 147-153.
19. Hansch, C. and Leo, A. J. (1979). Substituent Constants for Correlation Analysis in Chemistry and Biology. Wiley, New York.
20. Hansch, C. and Zhang, L. (1993). Quantitative structure-activity relationships of cytochrome P450, Drug Metab. Rev. 25, 1-48.
21. Hodgson, E. (2001). In vitro phase 1 metabolism of xenobiotics 1: pesticides and related chemicals used in agriculture and public health, J. Biochem. Mol. Toxicol. 15, 296-299.
22. Ioannides, C., Lewis, D. F. V. and Parke, D. V. (1995). Mechanisms of chemical carcinogenesis and molecular parametric analysis in the safety evaluation of chemicals, in: Drug, Diet and Disease, Volume 1. Mechanistic Approaches to Cancer, C. Ioannides and D. F. V. Lewis (Eds), pp. 1-46. Ellis Horwood, Chichester.
23. Karelson, M., Lobanov, V. S. and Katritzky, A. R. (1996). Quantum-chemical descriptors in QSAR/QSPR studies, Chem. Rev. 96, 1027-1043.
24. Kubinyi, H. (1997). QSAR and 3D QSAR in drug design. Part 2: applications and problems, Drug Discovery Today 2, 538-546.
25. oct from structure, Chem. Rev. 93, 1281-1306.
26. Lewis, D. F. V. (1986). MINDO/3: a review of the literature, Chem. Rev. 86, 1111-1123.
27. Lewis, D. F. V. (1990). MO-QSARs: a review of molecular orbital-generated quantitative structure-activity relationships, Progr. Drug Metab. 12, 205-255.
28. Lewis, D. F. V. (1992a). Computer modelling of cytochromes P450 and their substrates: a rational approach to the prediction of carcinogenicity, Front. Biotransform. 7, 90-136.
29. Lewis, D. F. V. (1992b). Computer-assisted methods in the evaluation of chemical toxicity, Rev. Comput. Chem. 3, 173-222.
30. Lewis, D. F. V. (1994a). Comparison between rodent carcinogenicity test results of 44 chemicals and a number of predictive systems, Regul. Toxicol. Pharmacol. 20, 215-222.
31. Lewis, D. F. V. (1994b). Molecular structural studies in the rationalization of xenobiotic metabolism and toxicity, Toxicol. Ecotoxicol. News 1, 108-112.
32. Lewis, D. F. V. (1995a). COMPACT and the importance of frontier orbitals in toxicity mediated by the cytochrome P450 mono-oxygenase system, Toxicol. Modeling 1, 85-97.
33. bm3), Xenobiotica 25, 333-366.
34. Lewis, D. F. V. (1996). Cytochromes P450: Structure, Function and Mechanism. Taylor and Francis, London.
35. Lewis, D. F. V. (1997d). Molecular modelling, in: Food Chemical Risk Analysis, D. R. Tennant (Ed.), Chapter 7, pp. 163-194. Chapman and Hall, London.
36. Lewis, D. F. V. (1997b). Quantitative structure-activity relationships in substrates, inducers and inhibitors of cytochrome P4501 (CYP1), Drug Metab. Rev. 29, 589-650.
37. Lewis, D. F. V. (1998). The CYP2 family: models, mutants and interactions, Xenobiotica 28, 617-661.
38. Lewis, D. F. V. (1999). Frontier orbitals in chemical and biological activity: quantitative relationships and mechanistic implications, Drug Metab. Rev. 31, 755-816.
39. Lewis, D. F. V. (2000a). On the recognition of mammalian microsomal cytochrome P450 substrates and their characteristics, Biochem. Pharmacol. 60, 293-306.
40. Lewis, D. F. V. (2000b). Structural characteristics of human P450s involved in drug metabolism: QSARs and lipophilicity profiles, Toxicology 144, 197-203.
41. Lewis, D. F. V. (2001a). COMPACT: a structural approach to the modelling of cytochromes P450 and their interactions with xenobiotics, J. Chem. Technol. Biotechnol. 76, 237-244.
42. Lewis, D. F. V. (2001b). Guide to Cytochromes P450 Structure and Function. Taylor and Francis, London.
43. Lewis, D. F. V. (2002a). Homology modelling of CYP2 family enzymes based on the CYP2C5 crystal structure, Xenobiotica 32 (in press).
44. Lewis, D. F. V. (2002b). Modelling human P450s involved in drug metabolism, J. Inorg. Biochem. (in press).
45. Lewis, D. F. V. (2002c). Molecular modeling of human P450-substrate interactions, Drug Metab. Rev. 34 (in press).
46. Lewis, D. F. V. (2002d). Oxidative stress: the role of cytochromes P450 in oxygen activation, J. Chem. Technol. Biotechnol. (in press).
47. Lewis, D. F. V. (2002e). Structural models for cytochrome P450-mediated catalysis, J. Chem. Technol. Biotechnol. (submitted).
48. Lewis, D. F. V. (2002f). Essential requirements for substrate binding affinity and selectivity towards human CYP2 family enzymes, Arch. Biochem. Biophys. (submitted).
49. Lewis, D. F. V. and Broughton, H. B. (2002). Molecular binding interactions: their estimation and rationalization in QSARs in terms of theoretically-derived parameters, The Scientific World (in press).
50. Lewis, D. F. V. and Dickins, M. (2001). Quantitative structure-activity relationships (QSARs) within series of inhibitors for mammalian cytochromes P450 (CYPs), J. Enzyme Inhib. 16, 321-330.
51. Lewis, D.F.V. and Dickins, M. (2002a). Baseline lipophilicity relationships in human cytochromes P450 associated with drug metabolism, Toxicology (submitted).
52. Lewis, D. F. V. and Dickins, M. (2002b). Factors influencing rates and clearance in P450-mediated reactions: QSARs for substrates of the xenobiotic-metabolizing hepatic microsomal P450s, Toxicology 170, 45-53.
53. Lewis, D. F. V. and Gorrod, J. W. (2002). Molecular orbital calculations and nicotine metabolism: a rationale for experimentally observed metabolite ratios, Drug Metab. Drug Interact. (in press).
54. Lewis, D. F. V. and Hlavica, P. (2000). Interactions between redox partners in various cytochrome P450 systems: functional and structural aspects, Biochim. Biophys. Acta 1460, 353-374.
55. Lewis, D. F. V. and Jacobs, M. N. (1999). A QSAR study of some PCBs' ligand binding affinity to the cytosolic Ah receptor (AhR), Organohalogen Compounds 41, 537-540.
56. Lewis, D. F. V. and Lake, B. G. (1997). A quantitative structure-activity relationship (QSAR) analysis for a series of rodent peroxisome proliferators: interaction with the mouse liver peroxisome proliferator-activated receptor α(mPPARα), Toxicol. Vitro 11, 99-105.
57. Lewis, D. F. V. and Lake, B. G. (1998). Molecular modelling of omeprazole interactions with cytochrome P450 isozymes is consistent with metabolism in human liver microsomes, Toxicology 125, 31-44.
58. Lewis, D. F. V. and Lake, B. G. (1999). Molecular modelling of CYP4A subfamily members based on sequence homology with CYP102, Xenobiotica 29, 763-781.
59. Lewis, D. F. V. and Lake, B. G. (2002). Species differences in coumarin metabolism: a molecular modelling evaluation of CYP2A interactions, Xenobiotica 32 (in press).
60. Lewis, D. F. V. and Langley, G. R. (1996). A validation study of the COMPACT and HazardExpert techniques with 40 chemicals, Mutation Res. 369, 157-174.
61. Lewis, D. F. V. and Lee-Robichaud, P. (1998). Molecular modelling of steroidogenic cytochromes P450 from families CYP11, CYP17, CYP19 and CYP21 based on the CYP102 crystal structure, J. Steroid Biochem. Mol. Biol. 66, 217-233.
62. Lewis, D. F. V. and Parke, D. V. (1995). The genotoxicity of benzanthracenes: a quantitative structure-activity study, Mutation Res. 328, 207-214.
63. Lewis, D. F. V. and Pratt, J. M. (1998). The P450 catalytic cycle and oxygenation mechanism, Drug Metabolism Reviews 30, 739-786.
64. Lewis, D. F. V. and Sheridan, G. (2001). Cytochromes P450, oxygen and evolution, Sci. World 1, 151-167.
65. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1986). Molecular dimensions of the substrate binding site of cytochrome P-448, Biochem. Pharmacol. 35, 2179-2185.
66. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1987). Structural requirements for substrates of cytochromes P-450 and P-448, Chemico-Biol. Interact. 64, 39-60.
67. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1989). Molecular orbital studies. Oxygen activation and mechanisms of cytochromes P450-mediated oxidative metabolism of xenobiotics, Chemico-Biol. Interact. 70, 263-280.
68. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1993). Validation of a novel molecular orbital approach (COMPACT) to the safety evaluation of chemicals by comparison with Salmonella mutagenicity and rodent carcinogenicity data evaluated by the US NCI/NTP, Mutation Res. 291, 61-77.
69. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1994a). Interaction of a series of nitriles with the alcohol inducible isoform of cytochrome P450: computer analysis of structure-activity relationships, Xenobiotica 24, 401-408.
70. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1994b). Molecular modelling of cytochrome P4501A1: a putative access channel explains differences in induction potency between the isomers benzo(a)pyrene and benzo(e)pyrene and 2- and 4-acetylaminofluorene, Toxicol. Lett. 71, 235-243.
71. Lewis, D. F. V., Lake, B. G., Ioannides, C., et al. (1994c). Inhibition of hepatic aryl hydrocarbon hydroxylase activity by a series of 7-hydroxycoumarins: QSAR studies, Xenobiotica 24, 829-838.
72. Lewis, D. F. V., Moereels, H., Lake, B. G., et al. (1994d). Molecular modeling of enzymes and receptors involved in carcinogenesis: QSARs and COMPACT-3D, Drug Metab. Rev. 26, 261-285.
73. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1995a). A quantitative structure-activity relationship study on a series of 10 para-substituted toluenes binding to cytochrome P4502B4 (CYP2B4) and also their hydroxylation rates, Biochem. Pharmacol. 50, 619-625.
74. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1995b). A retrospective evaluation of COMPACT predictions of rodent carcinogenicity testing from the NTP rodent bioassay results of 40 chemicals, Environ. Health Perspect. 103, 178-184.
75. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1995c). Computer graphics analysis of the interaction of alkoxymethylene dioxybenzenes with cytochrome P4501, Toxicol. Lett. 76, 39-45.
76. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1995d). Molecular orbital-generated QSARs in an homologous series of alkoxyresorufins and studies of their interactive docking with cytochromes P450, Xenobiotica 25, 1355-1369.
77. Lewis, D. F. V., Ioannides, C., Parke, D. V., et al. (1995e). Quantitative structure-activity relationships in some cooked food mutagens, Food Add. Contamin. 12, 715-724.
78. Lewis, D. F. V., Eddershaw, P. J., Goldfarb, P. S., et al. (1996). Molecular modelling of CYP3A4 form an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals, Xenobiotica 26, 1067-1086.
79. Lewis, D. F. V., Brantom, P. G., Ioannides, C., et al. (1997a). Nitrosamine carcinogenesis: rodent assays, quantitative structure-activity relationships and human risk assessment, Drug Metab. Rev. 29, 1055-1078.
80. Lewis, D. F. V., Eddershaw, P. J., Goldfarb, P. S. et al. (1997b). Molecular modelling of cytochrome P450 2D6 (CYP2D6) based on an alignment with CYP102: structural studies on specific CYP2D6 substrate metabolism, Xenobiotica 27, 319-340.
81. Lewis, D. F. V., Dickins, M., Eddershaw, P. J., et al. (1998a). Molecular modelling of human CYP2C subfamily enzymes CYP2C9 and CYP2C19: rationalization of substrate specificity and site-directed mutagenesis experiments in the CYP2C subfamily, Xenobiotica 28, 235-268.
82. Lewis, D. F. V., Eddershaw, P. J., Dickins, M., et al. (1998b). Structural determinants of P450 substrate specificity, binding affinity and catalytic rate, Chemico-Biol. Interact. 115, 175-199.
83. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1998c). A combined COMPACT and HazardExpert study of 40 chemicals for which information on mutagenicity and carcingenicity is known, including the results of human epidemiological studies, Human Exp. Toxicol. 17, 577-586.
84. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1998d). An improved and updated version of the COMPACT procedure for the evaluation of P450-mediated chemical activation, Drug Metab. Rev. 30, 709-737.
85. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1998e). Cytochrome P450 and species differences in xenobiotic metabolism and activation of carcinogens, Environ. Health Perspect. 106, 633-641.
86. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (1998f). Further validation of the COMPACT approach for the prospective safety evaluation of chemicals. Re-evaluation of 200 miscellaneous chemicals by comparison with rodent carcinogenicity data from the US NCI/NTP, Mutation Res. 412, 41-54.
87. Lewis, D. F. V., Watson, E. and Lake, B. G. (1998g). Evolution of the cytochrome P450 superfamily: sequence alignments and pharmacogenetics, Mutation Res. 410, 245-270.
88. Lewis, D. F. V., Dickins, M., Eddershaw, P. J., et al. (1999a). Cytochrome P450 substrate specificities, substrate structural templates and enzyme active site geometries, Drug Metab. Drug Interact. 15, 1-49.
89. Lewis, D. F. V., Dickins, M., Lake, B. G., et al. (1999b). Molecular modelling of the human cytochrome P450 isoform CYP2A6 and investigations of CYP2A substrate selectivity, Toxicology 133, 1-33.
90. Lewis, D. F. V., Lake, B. G., Dickins, M., et al. (1999c). Molecular modelling of the phenobarbital-inducible P450 isoforms: CYP2B1, CYP2B4 and CYP2B6 by homology with the substrate-bound CYP102 crystal structure, and evaluation of CYP2B substrate binding affinity, Xenobiotica 29, 361-393.
91. Lewis, D. F. V., Lake, B. G., George, S., et al. (1999d). Molecular modelling of CYP1 family isoforms CYP1A1, CYP1A2, CYP1A6 and CYP1B1 based on sequence homology with CYP102, Toxicology 139, 53-79.
92. Lewis, D. F. V., Wiseman, A. and Tarbit, M. H. (1999e). Molecular modelling of lansterol 14α-demethylase (CYP51) from Saccharomuces Cerevisiae via homology with CYP102, a unique bacterial cytochrome P450 isoform: quantitative structure-activity relationships (QSARs) within a number of antifungal agents, J. Enzyme Inhib. 14, 175-192.
93. Lewis, D. F. V., Bird, M. G., Dickins, M., et al. (2000a). Molecular modelling of human CYP2E1 by homology with the CYP102 haemoprotein domain: investigation of the interactions of substrates and inhibitors within the putative active site of the human CYP2E1 isoform, Xenobiotica 30, 1-25.
94. Lewis, D. F. V., Ioannides, C., Parke, D. V., et al. (2000b). Quantitative structure-activity relationships in a series of endogenous and synthetic steroids exhibiting induction of CYP3A activity and hepatomegaly associated with increased DNA synthesis, J. Steroid Biochem. Mol. Biol. 74, 179-185.
95. Lewis, D. F. V., Lake, B. G., Bird, M. G., et al. (2000c). Molecular modelling of human CYP2E1 by homology with the CYP102 haemoprotein domain: investigation of the interactions of substrates and inhibitors within the putative active site of the CYP2E1 isoform, Xenobiotica 30, 1-25.
96. Lewis, D. F. V., Modi, S. and Dickins, M. (2001). Quantitative structure-activity relationships (QSARs) within substrates of human cytochromes P450 involved in drug metabolism, Drug Metab. Drug Interact. 18, 221-242.
97. Lewis, D. F. V., Bird, M. G. and Jacobs, M. N. (2002a). Human carcinogens: an evaluation study via the COMPACT and HazardExpert procedures, Human Exp. Toxicol. (in press).
98. Lewis, D. F. V., Ioannides, C. and Parke, D. V. (2002b). A quantitative structure-activity relationship (QSAR) study of mutagenicity in several series of organic chemicals likely to be activated by cytochrome P450 enzymes, Mutation Res. (submitted).
99. Lewis, D. F. V., Jacobs, M. N., Dickins, M., et al. (2002c). Molecular modelling of the peroxisome proliferator-activated receptor α(PPARα) from human, rat and mouse, based on homology with the human PPARγ crystal structure, Toxicol. Vitro 16 (in press).
100. Lewis, D. F. V., Jacobs, M. N., Dickins, M., et al. (2002d). Quantitative structure-activity relationships for inducers of cytochrome P450 and nuclear receptor ligands involved in P450 regulation within the CYP1, CYP2, CYP3 and CYP4 families, Toxicology (in press).
101. Lewis, D. F. V., Modi, S. and Dickins, M. (2002e). Structure-activity relationships for human P450 substrates and inhibitors, Drug Metab. Rev. 34 (in press).
102. Lewis, D. F. V., Ogg, M. S., Goldfarb, P. S. and Gibson, G. G. (2002f). Molecular modelling of the human glucocorticoid receptor (hGR) ligand binding domain (LBD) by homology with the human estrogen receptor α(hERα) LBD: quantitative structure-activity relationships within a series of CYP3A4 inducers where induction is mediated via hGR invovlement, J. Steroid Biochem. Mol. Biol. (submitted).
103. Livingstone, D. J. (2000). The characterization of chemical structures using molecular properties. A survey, J. Chem. Inform. Comput. Sci. 40, 195-209.
104. Marcus, R. A. and Sutin, N. (1985). Electron transfers in chemistry and biology, Biochim. Biophys. Acta 811, 265-322.
105. Moser, C. C. and Dutton, P. L. (1992). Engineering protein structure for electron transfer function in photosynthetic reaction centres, Biochim. Biophys. Acta 1101, 171-176.
106. Parke, A. L., Ioannides, C., Lewis, D. F. V., et al. (1991). Molecular pathology of drug-disease interactions in chronic autoimmune inflammatory diseases, Inflammopharmacology 1, 3-36.
107. Parke, D. V. (1994). The cytochromes P450 and mechanisms of chemical carcinogenesis, Environ. Health Perspect. 102, 852-853.
108. Pliska, V., Testa, B. and van de Waterbeemd, H. (1996). Lipophilicity in Drug Action and Toxicity. VCH, Weinheim.
109. Rendic, S. and DiCarlo, F. J. (1997). Human cytochrome P450 enzymes: a status report summarizing their reactions, substrate, inducers and inhibitors, Drug Metab. Rev. 29, 413-580.
110. Rigby, M., Smith, E. B., Wakeham, W. A., et al. (1986). The Forces between Molecules. Clarendon Press, Oxford.
111. Rodrigues, A. D. and Lin, J. H. (2001). Screening of drug candidates for their drug-drug interaction potential, Curr. Opin. Chem. Biol. 5, 396-401.
112. Sangster, J. (1989). Octanol-water partition coefficients of simple organic compounds, J. Phys. Chem. Ref. Data 18, 1111-1229.
113. Sarver, J. G., White, D., Erhardt, P., et al. (1997). Estimating xenobiotic half-lives in humans from rat data: influence of log P, Environ. Health Perspect. 105, 1204-1209.
114. Sharp, K. A., Nicholls, A., Fine, R. F., et al. (1991). Reconciling the magnitude of the microscopic and macroscopic hydrophobic effects, Science 252, 106-109.
115. Smith, D. A. (1994). Chemistry and enzymology: their use in the prediction of human drug metabolism, Eur. J. Pharm. Sci. 2, 69-71.
116. Smith, D. A. and Jones, B. C. (1992). Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes, Biochem. Pharmacol. 44, 2089-2098.
117. Smith, D. A., Ackland, M. J. and Jones, B. C. (1997a). Properties of cytochrome P450 isoenzymes and their substrates: Part 1: active site characteristics, Drug Discov. Today 2, 406-414.
118. Smith, D. A., Ackland, M. J. and Jones, B. C. (1997b). Properties of cytochrome P450 isoenzymes and their substrates: Part 2: active site characteristics, Drug Discov. Today 2, 479-486.
119. Tomlinson, E. S., Lewis, D. F. V., Maggs, J. L., et al. (1997). In vitro metabolism of side-chain cleaved dexamethasone (9αF-A) is CYP3A4 mediated: rationalization of CYP2A4 and CYP17 (17, 20 lyase) involvement in dexamethasone metabolism in vitro based on molecular modelling studies, Biochem. Pharmacol. 54, 605-611.
120. Tsantili-Kakoulidou, A., Panderi, I., Csizmadia, F., et al. (1997). Prediction of distribution coefficient from structure. 2. Validation of Prolog D, an expert system, J. Pharm. Sci. 86, 1173-1179.
121. Vaes, W. H. J., Ramos, E. U., Vershaar, H. J. M., et al. (1998). Understanding and estimating membrane/water partition coefficients: approaches to derive quantitative structure property relationships, Chem. Res. Toxicol. 11, 847-854.
122. Williams, D. H., Cox, J. P. L., Doig, A. J., et al. (1991). Toward the semi-quantitative estimation of binding constants, J. Am. Chem. Soc. 113, 7020-7030.
123. 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 interaction: potential importance to its proposed anticarcinogenic/carcinogenic actions, Carcinogenesis 17, 1357-1360.