Evolution of the cytochrome P450 superfamily: Sequence alignments and pharmacogenetics

Mutation Research - Reviews in Mutation Research

Volumn 410, Issue 3, 1998, Pages 245-270

  Lewis, D F V ^a   Watson, E ^a   Lake, B G ^b  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b BIBRA INTERNATIONAL   (United Kingdom)

Author keywords

Cytochrome P450; Evolution; Pharmacogenetics; Sequence alignment

Indexed keywords

CYTOCHROME P450;

COMPARATIVE ANATOMY; ENZYME ANALYSIS; GENETIC POLYMORPHISM; GEOLOGY; MOLECULAR BIOLOGY; NONHUMAN; PHYLOGENY; PRIORITY JOURNAL; REGULATORY MECHANISM; REVIEW; SEQUENCE ANALYSIS; SPECIES DIFFERENCE; STRAIN DIFFERENCE;

EID: 0032102916     PISSN: 13835742     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5742(97)00040-9     Document Type: Article

References (132)

1. Nelson D.R., Kamataki T., Waxman D.J., Guengerich F.P., Estabrook R.W., Feyereisen R., Gonzalez F.J., Coon M.J., Gunsalus I.C., Gotoh O., Okuda K., Nebert D.W. The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes and nomenclature. DNA Cell Biol. 12:1993;1-51.
2. 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., Nebert D.W. P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics. 6:1996;1-42.
3. D.W. Nebert, J.E. Jones, J. Owens, A. Puga, Evolution of the P450 gene superfamily, in: T.E. King, H.S. Mason, M. Morrison (Eds.), Oxidases and Related Redox Systems, Alan R. Liss, New York, 1988, pp. 557-576.
4. Nebert D.W., Nelson D.R., Adesnik M., Coon M.J., Estabrook R.W., Gonzalez F.J., Guengerich F.P., Gunsalus I.C., Johnson E.F., Kemper B., Levin W., Phillips I.R., Sato R., Waterman M.R. The P450 superfamily: updated listing of all genes and recommended nomenclature for the chromosomal loci. DNA. 8:1989;1-13.
5. Nebert D.W., Nelson D.R., Feyereisen R. Evolution of the cytochrome P450 genes. Xenobiotica. 19:1989;1149-1160.
6. D.W. Nebert, D.R. Nelson, M.J. Coon, R.W. Estabrook, R. Feyereisen, Y. Fujii-Kuriyama, F.J. Gonzalez, F.P. Guengerich, I.C. Gunsalus, E.F. Johnson, J.C. Loper, R. Sato, M.R. Waterman, D.J. Waxman, The P450 superfamily: update on new sequences, gene mapping, and recommended nomenclature, 10 (1991) 1-14.
7. Nelson D.R., Strobel H.W. Evolution of cytochrome P450 proteins. Mol. Biol. Evol. 4:1987;572-593.
8. D.F.V. Lewis, Cytochromes P450: structure, function and mechanism, Taylor and Francis, London, 1996.
9. Nebert D.W., Gonzalez F.J. P450 genes: structure, evolution and regulation. Annu. Rev. Biochem. 56:1987;945-953.
10. Gonzalez F.J., Nebert D.W. Evolution of the P450 gene superfamily. Trends Genet. 6:1990;182-186.
11. Nebert D.W., Negishi M. Multiple forms of cytochrome P450 and the importance of molecular biology and evolution. Biochem. Pharmacol. 31:1982;2311-2317.
12. Y. Imai, Classification and list of cytochrome P450, in: T. Omura, Y. Ishimura, Y. Fujii-Kuriyama (Eds.), Cytochrome P450 Kodansha, Tokyo, 1993, pp. 273-286.
13. Mojzsis S.J., Arrhenius G., McKeegan K.D., Harrison T.M., Nutman A.P., Friend C.R.L. Evidence for life on earth before 3800 million years ago. Nature. 384:1996;55-59.
14. Nebert D.W., Nelson D.R. P450 gene nomenclature based on evolution. Methods Enzymol. 206:1991;3-11.
15. Gotoh O., Fujii-Kuriyama Y. Evolution, structure and gene regulation of cytochrome P450. Front. Biotransformation. 1:1989;195-243.
16. Y. Fujii-Kuriyama, H. Kimura, Y. Higashi, K. Sogawa, H. Inoue, T. Shimizu, M. Hatano, O. Gotoh, Structural characteristics of cytochrome P450 molecules, in: I. Schuster (Ed.), Cytochrome P450: Biochemistry and Biophysics, Taylor and Francis, London, 1989, pp. 445-463.
17. O. Gotoh, Evolution and differentiation of P450 genes, in: T. Omura, Y. Ishimura, Y. Fujii-Kuriyama (Eds.), Cyotchrome P450, Kodansha, Tokyo, 1993, pp. 255-272.
18. Puga A., Nebert D.W. Evolution of the P450 gene superfamily and regulation of the murine CYP1A1 gene. Biochem. Soc. Trans. 18:1990;7-10.
19. Degtyarenko K.N., Archakov A.I. Molecular evolution of P450 superfamily and P450-containing monooxygenase systems. FEBS Lett. 332:1993;1-8.
20. P.R. Ortiz de Montellano, S.E. Graham-Lorence, Structure of cytochrome P450: heme-binding site and heme reactivity, in: J.B. Schenkman, H. Griem (Eds.), Cytochrome P450 Springer-Verlag, Berlin, 1993, pp. 169-181.
21. Ravichandran K.G., Boddupalli S.S., Haseman C.A., Peterson J.A., Deisenhofer J. Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450s. Science. 261:1993;731-736.
22. bm3). Xenobiotica. 25:1995;333-366.
23. cam. J. Mol. Biol. 195:1987;687-700.
24. terp at 2.3 Å J. Mol. Biol. 236:1994;1160-1185.
25. eryF involved in erythromycin biosynthesis. Structural Biol. 2:1995;144-152.
26. Gerber N.C., Sligar S.G. Catalytic mechanism of cytochrome P450: evidence of a distal charge relay. J. Am. Chem. Soc. 114:1992;8742-8743.
27. cam oxygen activation. J. Biol. Chem. 269:1994;4260-4266.
28. Gotoh O. Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 267:1992;83-90.
29. L. Margulis, D. Sagan, What is Life? Weidenfeld and Nicolson, London, 1995.
30. J.S. Levine, The origin and evolution of atmospheric oxygen, in: T.E. King, H.S. Mason, M. Morrison (Eds.), Oxidases and Related Redox Systems, Alan R. Liss, New York, 1988, pp. 111-126.
31. Canfield D.E., Teske A. Late Proterozoic rise in atmospheric oxygen concentration inferred from phylogenetic and sulphur-isotope studies. Nature. 382:1996;127-132.
32. Knoll A.H. Breathing room for early animals. Nature. 382:1996;111-112.
33. Knoll A.H. The early evolution of eukaryotes: a geological perspective. Science. 256:1992;622-627.
34. J.W. Schopf, C. Klein (Eds.), The Proterozoic Biosphere, Cambridge Univ. Press, Cambridge, 1992.
35. Yang D., Oyaizu Y., Oyaizu H., Olsen G.J., Woese C.R. Mitochondrial origins. Proc. Natl. Acad. Sci. U.S.A. 82:1985;4443-4447.
36. Woese C.R. Bacterial evolution. Microbiol. Rev. 51:1987;221-271.
37. M.O. Dayhoff, Atlas of Protein Sequence and Structure, Vol. 5, Supplement 3, National Biomedical Research Foundation, Washington, 1978.
38. Keller M., Blöchl E., Wächtershäuser G., Stetter K.O. Formation of amide bonds without a condensation agent and implications for origin of life. Nature. 368:1994;836-838.
39. L. Margulis, Early cellular evolution, in: C. Ponnamperuma (Ed.), Exobiology, North-Holland, Amsterdam, 1972, pp. 342-368.
40. Bryant C. Doing without oxygen. Biologist. 40(2):1993;58-61.
41. Kelly R.M., Baross J.A., Adams M.W.W. Life in boiling water. Chem. Britain. 30:1994;555-558.
42. S. Potter, The abyss gazes also: the lives and times of the early archaebacteria, The Biologist, Oct./Nov. issue, 1992, pp. 10-12.
43. Wheelis M.L., Kandler O., Woese C.R. On the nature of global classification. Proc. Natl. Acad. Sci. U.S.A. 89:1992;2930-2934.
44. R.K. Selander, A.G. Clark, T.S. Whittam (Eds.), Evolution at the Molecular Level, Sinauer, Sutherland, MA, 1991.
45. Wickramasinghe R.H., Villee C.A. Early role during chemical evolution for cytochrome P450 in oxygen detoxification. Nature. 256:1975;509-511.
46. Berkner L.V., Marshall L.C. On the origin and rise of oxygen concentration in the earth's atmosphere. J. Atmos. Sci. 22:1965;225-261.
47. J.D. Bernal, The Origins of Life, Weidenfeld and Nicholson, London, 1967.
48. Cloud P. Beginnings of biospheric evolution and their biogeochemical consequences. Paleobiology. 2:1976;351-387.
49. D.S. Bendall (Ed.), Evolution from Molecules to Men, Cambridge Univ. Press, Cambridge, 1983.
50. M.O. Dayhoff, Atlas of Protein Sequence and Structure, Vol. 5, National Biomedical Research Foundation, Washington, 1972.
51. T.E. Creighton, Proteins: Structures and Molecular Properties, 2nd edn., Freeman, New York, 1993.
52. M. Ridley, Evolution, 2nd edn., Blackwell, Cambridge, MA, 1996.
53. Hedges S.B., Parker P.H., Sibley C.G., Kumar S. Continental break-up and the ordinal diversification of birds and mammals. Nature. 381:1996;226-229.
54. Matese J., Whitmire D. Tidal imprint of distant galactic matter on the Oort comet cloud. Astrophysical J. 472:1996;L41-L43.
55. Gribben J. Galactic tides bring showers of comets to Earth. New Scientist. 152(2060):1996;15.
56. J. Lovelock, The Ages of Gaia, Oxford Univ. Press, Oxford, 1988.
57. Doolittle R.F., Feng D.-F., Tsang S., Cho G., Little E. Determining divergence times of the majors kingdoms of living organisms with a protein clock. Science. 271:1996;470-477.
58. Negishi M., Iwasaki M., Juvonen R.O., Sueyoshi T., Darden T.A., Pedersen L.G. Structural flexibility and functional versatility of cytochrome P450 and rapid evolution. Mut. Res. 350:1996;43-50.
59. W.B. Harland, R.L. Armstrong, L.E. Craig, A.G. Smith, D.G. Smith, A Geological Time Scale, Cambridge Univ. Press, Cambridge, 1989.
60. Nebert D.W. Polymorphisms in drug-metabolizing enzymes: what is their clinical relevance and why do they exist? Am. J. Hum. Genet. 60:1997;265-271.
61. Tajima F., Nei M. Estimation of evolutionary distance between nucleotide sequences. Mol. Biol. Evol. 1:1984;269-285.
62. Cohen M.B., Feyereisen R. A cluster of cytochrome P450 genes of the CYP6 family in the house fly. DNA Cell Biol. 14:1995;73-82.
63. Guengerich F.P. Cytochrome P450 enzymes. Am. Scientist. 81:1993;440-447.
64. Martin A.P., Palumbi S.R. Body size, metabolic rate, generation time, and the molecular clock. Proc. Natl. Acad. Sci. U.S.A. 90:1993;4087-4091.
65. Orr W.C., Sohal R.S. Extension of life-span by overexpression of superoxide dismutase and catalase in Drosophila melanogaster. Science. 263:1994;1128-1130.
66. Horn E.P., Tucker M.E., Lambert G., Silverman G., Zametkin D., Sinha R., Hartge T., Landi M.T., Cuporaso M.E. Cancer Epidemiol. Biomarkers Prev. 4:1995;529-533.
67. Hoffman S.M.G., Fernandez-Salguero P., Gonzalez F.J., Mohrenweiser H.W. Organization and evolution of the cytochrome P450 CYP2A-2B-2F subfamily gene cluster on human chromosome 19. J. Mol. Evol. 41:1995;894-900.
68. Gonzalez F.J. The molecular biology of cytochrome P450s. Pharmacological Rev. 40:1989;243-288.
69. Lewis D.F.V., Lake B.G. Molecular modelling of members of the P4502A subfamily: application to studies of enzyme specificity. Xenobiotica. 25:1995;585-598.
70. H. Raunio, O. Pelkonen, Cancer genetics, in: C. Ioannides, D.F.V. Lewis (Eds.), Drugs, Diet and Disease, Vol. 1, Mechanistic Approaches to Cancer, Ellis Horwood, Chichester, 1995, pp. 229-258.
71. Gonzalez F.J., Idle J.R. Pharmacogenetic phenotyping and geotyping: present status and future potential. Clin. Pharmacokinet. Concepts. 26:1996;59-70.
72. Nebert D.W., McKinnon R.A., Puga A. Human drug-metabolizing enzyme polymorphisms: effects on risk of toxicity and cancer. DNA Cell Biol. 15:1996;273-280.
73. Daly A.K., Brockmöller J., Broly F., Eichelbaum M., Evans W.E., Gonzalez F.J., Huang J.-D., Idle J.R., Ingelman-Sundberg M., Ishizaki T., Jacqz-Aigrain E., Meyer U.A., Nebert D.W., Steem V.M., Wolf C.R., Zanger U.M. Nomenclature for human CYP2D6 alleles. Pharmacogenetics. 6:1996;193-201.
74. Daly A.K., Steen V.M., Fairbrother K.S., Idle J.R. CYP2D6 multiallelism. Methods Enzymol. 272:1996;199-210.
75. D.A. Price-Evans, Genetic Factors in Drug Therapy, Cambridge Univ. Press, Cambridge, 1993.
76. Inaba T., Nebert D.W., Burchell B., Watkins P.B., Goldstein J.A., Bertilsson L., Tucker G.T. Pharmacogenetics in clinical pharmacology and toxicology. Can. J. Physiol. Pharmacol. 73:1995;331-338.
77. Goldstein J.A., Blaisdell J. Genetic tests which identify the principal defects in CYP2C19 responsible for the polymorphism in mephenytoin metabolism. Methods Enzymol. 272:1996;210-218.
78. Kawajiri K., Watanabe J., Hayashi S.-I. Identification of allelic variants of the human CYP1A1 gene. Methods Enzymol. 272:1996;226-232.
79. K. Kawajiri, S.-I. Hayashi, The CYP1 family, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 77-97.
80. Lewis D.F.V., Lake B.G. Molecular modelling of CYP1A subfamily members based on an alignment with CYP102: rationalization of CYP1A substrate specificity in terms of active site amino acid residues. Xenobiotica. 26:1996;723-753.
81. Fernandez-Salguero P., Hoffman S.M.G., Cholerton S., Mohrenweiser H., Raunio H., Rautio A., Pelkonen O., Huang J.-D., Evans W.E., Idle J.R., Gonzalez F.J. A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles. Am. J. Hum. Genet. 57:1995;651-660.
82. T.K.H. Chang, D.J. Waxman, The CYP2A subfamily, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 99-134.
83. Inoue K., Yamazaki H., Imiya K., Akasaka S., Guengerich F.P., Shimada T. Relationship between CYP2C9 and 2C19 genotypes and tolbutamide methyl hydroxylation and S-mephenytoin 4′-hydroxylation activities in livers of Japanese and Caucasian populations. Pharmacogenetics. 7:1997;103-113.
84. F.J. Gonzalez, The CYP2D subfamily, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 183-210.
85. Tucker G.T., Lennard M.S., Ellis S.W., Woods H.F., Lin L., Hiratsuka A., Chu T., Cho A.K. 'Ecstasy' is demethylated by human cyctochrome P4502D6 (CYP2D6). Br. J. Clin. Pharmacol. 36:1993;144P.
86. M.J.J. Ronis, K.O. Lindros, M. Ingelman-Sundberg, The CYP2E subfamily, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 221-239.
87. Nedelcheva V., Persson I., Ingelman-Sundberg M. Genetic polymorphism of human cytochrome P450 2E1. Methods Enzymol. 272:1996;218-225.
88. P. Maurel, The CYP3 family, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 241-270.
89. Gonzalez F.J., Gelboin H.V. Human cytochromes P450: evolution, catalytic activities and interindividual variations in expression. Prog. Clin. Biol. Res. 372:1991;11-20.
90. Caporaso N., Landl M.T., Vineis P. Relevance of metabolic polymorphisms to human carcinogenesis: evaluation of epidemiological evidence. Pharmacogenetics. 1:1991;4-19.
91. Boobis A.R., Sesardic D., Murray B.P., Edwards R.J., Singleton A.M., Rich K.J., Murray S., De la Torre R., Segura J., Pelkonen O., Pasanen M., Kobayashi S., Zhi-Guang T., Davies D.S. Species variation in the response of the cytochrome P450-dependent mono-oxygenase system to inducers and inhibitors. Xenobiotica. 20:1990;1139-1161.
92. G.G. Gibson, P. Skett, Introduction to Drug Metabolism, Blackie, London, 1994.
93. B.F. Windley, The Evolving Continents, 3rd edn., Wiley, New York, 1995.
94. Lewis D.F.V., Bird M.G., Parke D.V. Molecular modelling of CYP2E1 enzymes from rat, mouse and man: a possible explanation for the species differences in butadiene metabolism, and rationalization of CYP2E substrate specificity. Toxicology. 118:1997;93-113.
95. Wiseman H., Lewis D.F.V. The metabolism of tamoxifen by human cytochromes P450 is reationalized by molecular modelling of the enzyme-substrate interaction: potential importance to its proposed anticarcinogenic/carciongenic actions. Carcinogenesis. 17:1996;1357-1360.
96. D.F.V. Lewis, B.G. Lake, Molecular modelling of omeprazole interactions with cytochrome P450 isozymes is consistent with metabolism in human liver microsomes, Toxicology (1997) in press.
97. Lewis D.F.V., Moereels H. The sequence homologies of cytochromes P450 and active site geometries. J. Comput.-Aided Mol. Des. 6:1992;235-252.
98. Lewis D.F.V. Computer modelling of cytochromes P450 and their substrates: a rational approach to the prediction of carcinogenicity. Front. Biotransformation. 7:1992;90-136.
99. Mancy A., Bruto P., Dijols S., Dansette P.M., Mansuy D. The substrate binding site of human liver cytochrome P450 2C9: an approach using designed tienilic acid derivatives and molecular modeling. Biochemistry. 34:1995;10365-10375.
100. D.F.V. Lewis, Molecular modelling of mammalian cytochromes P450, in: C. Ioannides (Ed.), Cytochrome P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 355-398.
101. Korzekwa K.R., Jones J.P. Predicting the cytochrome P450 mediated metabolism of xenobiotics. Pharmacogenetics. 3:1993;1-18.
102. Szklarz G.D., Ornstein R.L., Halpert J.R. Application of 3-dimensional homology, modeling of cytochrome P450 2B1 for interpretation of site-directed mutagenesis results. J. Biomecular Structure Dynamics. 12:1994;61-78.
103. Koymans L.M.H., Vermeulen N.P.E., Baarslag A., Donne-Opden Kelder G.M. A preliminary 3D model for cytochrome P450 2D6 constructed by homology model building. J. Comp.-Aided Mol. Des. 7:1993;281-289.
104. cam. J. Mol. Graph. 12:1994;185-192.
105. Hasemann C.A., Kurumbail R.G., Boddupalli S.S., Peterson J.A., Deisenhofer J. Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure. 3:1995;41-62.
106. J.A. Peterson, S. Graham-Lorence, Bacterial P450s: structural similarities and functional differences, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450, Plenum, New York, 1995, pp. 151-180.
107. Graham-Lorence S., Peterson J.A. P450s: structural similarities and functional differences. FASEB J. 10:1996;206-214.
108. Nelson D.R., Strobel H.W. On the membrane topology of vertebrate cytochrome P450 proteins. J. Biol. Chem. 263:1988;6038-6050.
109. cam. Biochemistry. 28:1989;656-660.
110. Graham-Lorence S., Peterson J.A. Structural alignments of P450s and extrapolations to the unknown. Methods Enzymol. 272:1996;315-326.
111. Edwards R.J., Murray B.P., Boobis A.R., Davies D.S. Identification and location of α-helices in mammalian cytochromes P450. Biochemistry. 28:1989;3762-3770.
112. Kalb V.F., Loper J.C. Proteins from eight eukaryotic cytochrome P450 families share a segmented region of sequence similarity. Proc. Natl. Acad. Sci. U.S.A. 85:1988;7221-7225.
113. cam. Eur. J. Biochem. 198:1993;307-315.
114. D.R. Nelson, Cytochrome P450 nomenclature and alignment of selected sequences, in: P.R. Ortiz de Montellano (Ed.), Cytochrome P450, Plenum, New York, 1995, pp. 575-606.
115. Tretiakov V.E., Degtyarenko K.N., Uvarov V.Y., Archakov A.I. Secondary structure and membrane topology of cytochromes P450s. Arch. Biochem. Biophys. 275:1989;429-439.
116. Tretiakov V.E., Degtyarenko K.N., Uvarov V.Y., Archakov A.I., Tretyakova L.Z., Varenitsa A.I. Secondary structure and membrane topology of cytochromes P450. Mol. Biol. 23:1989;1047-1056.
117. O. Gotoh, P450 genes and their expression, in: T. Omura, Y. Ishimura, Y. Fujii-Kuriyama (Eds.), Cytochrome P450, Kodansha, Tokyo, 1993, pp. 207-223.
118. cam and BM-3 as templates: implications for the substrate binding pocket. Protein Eng. 7:1994;1345-1351.
119. D.F.V. Lewis, Molecular modelling of cytochromes P450, in: H. van de Waterbeemd, B. Testa, G. Folkers (Eds.), Computer-Assisted Lead Finding and Optimization, Verlag Helvetica Chimica Acta, Basel, 1997, pp. 333-354.
120. Ellis S.W., Rowland K., Ackland M.J., Rekka E., Simula A.P., Lennard M.S., Wolf C.R., Tucker G.T. Influence of amino acid residue 374 of cytochrome P450 2D6 (CYP2D6) on the regio- and enantio-selective metabolism of metoprolol. Biochem. J. 316:1996;647-654.
121. B.G. Lake, D.F.V. Lewis, The CYP4 family, in: C. Ioannides (Ed.), Cytochromes P450: Metabolic and Toxicological Aspects, CRC Press, Boca Raton, FL, 1996, pp. 271-297.
122. Lewis D.F.V., Lake B.G. Molecular modelling of mammalian CYP2B isoforms and their interaction with substrates, inhibitors and redox components. Xenobiotica. 27:1997;443-478.
123. D.F.V. Lewis, P. Lee-Robichaud, Molecular modelling of steroidogenic cytochromes P450 from families CYP11, CYP17, CYP19 and CYP21 based on the CYP102 crystal structure, J. Steroid Biochem. Mol. Biol. (1997) in press.
124. Lewis D.F.V., Lake B.G., Parke D.V. Molecular orbital-generated QSARs in a homologous series of alkoxyresorufins and studies of their interactive docking with P450s. Xenobiotica. 25:1995;1355-1369.
125. Szklarz G.D., He Y.A., Halpert J.R. Site-directed mutagenesis as a tool for molecular modeling of cytochrome P450 2B1. Biochemistry. 34:1995;14312-14322.
126. BM3. Anti-Cancer Drug Des. 12:1997;113-123.
127. Lewis D.F.V., Eddershaw P.J., Goldfarb P.S., Tarbit M.H. Molecular modelling of CYP3A4 from an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica. 26:1996;1067-1086.
128. Lewis D.F.V., Eddershaw P.J., Goldfarb P.S., Tarbit M.H. Molecular modelling of cytochrome P4502D6 (CYP2D6) based on an alignment with CYP102: structural studies on specific CYP2D6 substrate metabolism. Xenobiotica. 27:1997;319-340.
129. D.F.V. Lewis, M. Dickins, P.J. Eddershaw, P.S. Goldfarb, M.H. Tarbit, Molecular modelling of human CYP2C subfamily enzymes CYP2C9 and CYP2C19: rationalization of substrate specificity and site-directed mutagenesis experiments in the CYP2C subfamily, Xenobiotica (1997) in press.
130. Chothia C., Lesk A. The relation between the divergence of sequence and structure in proteins. EMBO J. 5:1986;823-826.
131. Creighton T.E., Darby N.J. Functional evolutionary divergence of proteolytic enzymes and their inhibitors. Trends Biol. Sci. 14:1989;319-324.
132. S.F. Mason, Chemical evolution: origin of the elements, Molecules and Living Systems, Clarendon Press, Oxford, 1992.