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Reviews on structure and function of P450 proteins

  1. Adesnik, M. and Atchison, M. (1986) Genes for cytochrome P­450 and their regulation. CRC Crit. Rev. Biochem. 19, 247-305.
  2. Andersson, L.A. and Dawson, L.A. (1991) EXAFS spectroscopy of heme­containing oxygenases and peroxidases. Structure and Bonding 64, 1-40.
  3. Archakov, A.I., Zgoda, V.G. and Karuzina, I.I. (1998) Oxidative modification of cytochrome P450 and other macromolecules during its turnover. Vopr. Med. Khim. (Moscow) 44, 3-27.
  4. Bernhardt, R. (1995) Cytochrome P450: structure, function, and generation of reactive oxygen species. Rev. Physiol. Biochem. Pharmacol. 127, 137-221.
  5. Bershtein, L.M. (1997) Molecular­genetic aspects of estrogen production. Aromatase gene. Mol. Biol. (Moscow) 31, 773-777.
  6. Black, S.D. and Coon, M.J. (1987) P­450 cytochromes: structure and function. Adv. Enzymol. Relat. Areas Mol. Biol. 60, 35-87.
  7. Buhler, D.R. and Wang­Buhler, J.L. (1998) Rainbow trout cytochrome P450s: purification, molecular aspects, metabolic activity, induction and role in environmental monitoring. Comp. Biochem. Physiol. C 121, 107-137.
  8. Chapman, S.K., Daff, S. amd Munro, A.W. (1997) Heme: the most versatile redox centre in biology? Structure and Bonding 88, 39-70.
  9. Chapple, C. (1998) Molecular­genetic analysis of plant cytochrome P450­dependent monooxygenases. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49, 311-343.
  10. Cholerton, S., Daly, A.K. and Idle, J.R. (1992) The role of individual human cytochromes P450 in drug metabolism and clinical response. Trends Pharmacol. Sci. 13, 434-439.
  11. Coon, M.J., Vaz, A.D.N. and Bestervelt, L.L. (1996) Peroxidative reactions of diversozymes. FASEB J. 10, 428-434.
  12. Coon, M.J., Vaz, A.D.N., McGinnity, D.F. and Peng, H.­M. (1998) Multiple activated oxygen species in P450 catalysis: Contributions to specificity in drug metabolism. Drug Metab. Dispos. 26, 1190-1193.
  13. Cupp, M.J. and Tracy, T.S. (1998) Cytochrome P450: new nomenclature and clinical implications. Am. Fam. Physician 57, 107-116.
  14. Cupp­Vickery, J.R. and Poulos, T.L. (1997) Structure of cytochrome P450eryF: substrate, inhibitors, and model compounds bound in the active site. Steroids 62, 112-116.
  15. Dahl, A.R. and Lewis, J.L. (1993) Respiratory tract uptake of inhalants and metabolism of xenobiotics. Annu. Rev. Pharmacol. Toxicol. 33, 383-407.
  16. Dawson, J.H. (1988) Probing structure­function relations in heme­containing oxygenases and peroxidases. Science 240, 433-439.
  17. Dawson, J.H. and Sono, M. (1987) Cytochrome P­450 and chloroperoxidase: thiolate­ligated heme enzymes. Spectroscopic determination of their active site structures and mechanistic implications of thiolate ligation. Chem. Rev. 87, 1255-1276.
  18. Degtyarenko, K.N. (1995) Structural domains of P450­containing monooxygenase systems. Protein Engineering 8, 737-747.
  19. Degtyarenko, K.N. and Archakov, A.I. (1993) Molecular evolution of P450 superfamily and P450­containing monooxygenase systems. FEBS Lett. 332, 1-8.
  20. Dolphin, D. (1985) Cytochrome P450: substrate and prosthetic­group free radicals generated during the enzymatic cycle. Philos. Trans. R. Soc. Lond. B 311, 579-591.
  21. Dolphin, D., Traylor, T.G. and Xie, L.Y. (1997) Polyhaloporphyrins: unusual ligands for metals and metal­catalyzed oxidations. Acc. Chem. Res. 30, 251-259.
  22. Durst, F., Benveniste, I., Salaün, J.­P. and Werck­Reichhart, D. (1992) Function, mechanism and regulation of cytochrome P­450 enzymes in plants. Biochem. Soc. Trans. 20, 353-357.
  23. Dus, K.M. (1982) Insights into the active site of the cytochrome P­450 haemoprotein family - A unifying concept based on structural considerations. Xenobiotica 12, 745-772.
  24. Eaton, D.L. and Gallagher, E.P. (1994) Mechanisms of aflatoxin carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 34, 135-172.
  25. Ellin, A. and Orrenius, S. (1975) Fatty acid hydroxylation in rat kidney cortex microsomes. Mol. Cell Biochem. 8, 69-79.
  26. Feyereisen, R. (1995) Molecular biology of insecticide resistance. Toxicol. Lett. 82-83, 83-90.
  27. Fulco, A.J. (1991) P450BM­3 and other inducible bacterial P450 cytochromes: biochemistry and regulation. Annu. Rev. Pharmacol. Toxicol. 31, 177-203.
  28. Gibson, G.G. (1989) Comparative aspects of the mammalian cytochrome P450 IV gene family. Xenobiotica 19, 1123-1148.
  29. Gillam, E.M.J. (1998) Human cytochrome P450 enzymes expressed in bacteria: reagents to probe molecular interactions in toxicology. Clin. Exp. Pharmacol. Physiol. 25, 877-886.
  30. Gonzalez, F.J. (1988) The molecular biology of cytochrome P450s. Pharmacol. Rev. 40, 243-288.
  31. Gonzalez, F.J. (1990) Molecular genetics of the P­450 superfamily. Pharmacol. Ther. 45, 1-38.
  32. Gonzalez, F.J. (1992) Human cytochromes P450: problems and prospects. Trends Pharmacol. Sci. 13, 346-352.
  33. Gonzalez, F.J. and Gelboin, H.V. (1992) Human cytochromes P450: evolution and cDNA-directed expression. Environ. Health Perspect. 98, 81-85.
  34. Gonzalez, F.J. and Korzekwa, K.R. (1995) Cytochromes P450 expression systems. Annu. Rev. Pharmacol. Toxicol. 35, 369-390.
  35. Gonzalez, F.J. and Nebert, D.W. (1990) Evolution of the P450 gene superfamily: animal-plant 'warfare', molecular drive and human genetic differences in drug oxidation. Trends Genet. 6, 182-186.
  36. Gonzalez, F.J., Jaiswal, A.K. and Nebert, D.W. (1986) P450 genes: evolution, regulation, and relationship to human cancer and pharmacogenetics. Cold Spring Harbor Symp. Quant. Biol. 51 Pt 2, 879-890.
  37. Graham­Lorence, S. and Peterson, J.A. (1996a) P450s: structural similarities and functional differences. FASEB J. 10, 206-214.
  38. Graham­Lorence, S. and Peterson, J.A. (1996b) Structural alignments of P450s and extrapolations to the unknown. Methods Enzymol. 272, 315-326.
  39. Greenblatt, D.J., von Moltke, L.L., Harmatz, J.S. and Shader, R.I. (1998) Drug interactions with newer antidepressants: role of human cytochromes P450. J. Clin. Psychiatry 59, Suppl 15, 19-27.
  40. Gross, Z. (1996) The effect of axial ligands on the reactivity and stability of the oxoferryl moiety in model complexes of Compound I of heme­dependent enzymes. J. Biol. Inorg. Chem. 1, 368-371.
  41. Groves, J.T. (1979) Cytochrome P­450 and other heme­containing oxygenases. In Eichhorn, G.L. and Marzilli, L.G., Eds. Advances in Inorganic Biochemistry, vol. 1. Elsevier North Holland, New York, pp. 119-145.
  42. Guengerich, F.P. (1990) Enzymatic oxidation of xenobiotic chemicals. Crit. Rev. Biochem. Mol. Biol. 25, 97-153.
  43. Guengerich, F.P. (1997) Comparisons of catalytic selectivity of cytochrome P450 subfamily enzymes from different species. Chem. Biol. Interact. 106, 161-182.
  44. Guengerich, F.P. and Parikh, A. (1997) Expression of drug­metabolizing enzymes. Curr. Opin. Biotechnol. 8, 623-628.
  45. Guengerich, F.P., Hosea, N.A., Parikh, A., Bell­Parikh, L.C., Johnson, W.W., Gillam, E.M.J. and Shimada, T. (1998) Twenty years of biochemistry of human P450s: purification, expression, mechanism, and relevance to drugs. Drug Metab. Dispos. 26, 1175-1178.
  46. Gunsalus, I.C., Pederson, T.C. and Sligar, S.G. (1975) Oxygenase­catalyzed biological hydroxylations. Annu. Rev. Biochem. 44, 377-407.
  47. Hall, P.F. (1989) Cytochromes P­450 in steroidogenesis: Are these enzymes more specific than those of drug metabolism? Clin. Exp. Pharmacol. Physiol. 16, 485-489.
  48. Hall, P.F. (1991) Cytochrome P­450 C21scc: One enzyme with two actions: hydroxylase and lyase. J. Steroid Biochem. Mol. Biol. 40, 527-532.
  49. Halpert, J.R. (1995) Structural basis of selective cytochrome P450 inhibition. Annu. Rev. Pharmacol. Toxicol. 35, 29-53.
  50. Halpert, J.R., Domanski, T.L., Adali, O., Biagini, C.P., Cosme, J., Dierks, E.A., Johnson, E.F., Jones, J.P., Ortiz de Montellano, P., Philpot, R.M., Sibbesen, O., Wyatt, W.K. and Zheng, Z. (1998) Structure-function of cytochromes P450 and flavin­containing monooxygenases: Implications for drug metabolism. Drug Metab. Dispos. 26, 1223-1231.
  51. Harayama, S., Kok, M. and Neidle, E.L. (1992) Functional and evolutionary relationships among diverse oxygenases. Annu. Rev. Microbiol. 46, 565-601.
  52. 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.
  53. Henry, Y., Lepoivre, M., Drapier, J.­C., Ducrocq, C., Boucher, J.­L. and Guissani, A. (1993) EPR characterization of molecular targets for NO in mammalian cells and organelles. FASEB J. 7, 1124-1134.
  54. Hill, H.A.O., Röder, A. and Williams, R.J.P. (1970) The chemical nature and reactivity of cytochrome P­450. Structure and Bonding 8, 123-151.
  55. Hodgson, E., Kulkarni, A.P., Fabacher D.L. and Robacker, K.M. (1980) Induction of hepatic drug metabolizing enzymes in mammals by pesticides: A review. J. Environ. Sci. Health B15, 723-754.
  56. Hodgson, E., Rose, R.L., Goh, D.K., Rock, G.C. and Roe, R.M. (1993) Insect cytochrome P­450: metabolism and resistance to insecticides. Biochem. Soc. Trans. 21, 1060-1065.
  57. Hollenberg, P.F. (1992) Mechanisms of cytochrome P450 and peroxidase­catalyzed xenobiotic metabolism. FASEB J. 6, 686-694.
  58. Honeck, H., Schunck, W.H. and Müller, H.G. (1985) The function of cytochrome P­450 in fungi and prospects of application. Pharmazie 40, 221-227.
  59. Honkakoski, P. and Negishi, M. (1997) The structure, function, and regulation of cytochrome P450 2A enzymes. Drug Metab. Rev. 29, 977-996.
  60. Honkakoski, P. and Negishi, M. (1998) Regulatory DNA elements of phenobarbital­responsive cytochrome P450 CYP2B genes. J. Biochem. Mol. Toxicol. 12, 3-9.
  61. Hruby, K. and Anzenbacher, P. (1997) Cytochrom P450 - Vyznam v biotransformaci xenobiotik a mezidruhove srovnani. [Cytochrome P450 - Its significance in the biotransformation of xenobiotics and interspecies comparisons] Cesk. Fysiol. 46, 34-39.
  62. James, M.O. (1989) Cytochrome P450 monooxygenases in crustaceans. Xenobiotica 19, 1063-1076.
  63. James, M.O. and Boyle, S.M. (1998) Cytochromes P450 in crustacea. Comp. Biochem. Physiol. C 121, 157-172.
  64. Jarman, M., Smith, H.J., Nicholls, P.J. and Simons, C. (1998) Inhibitors of enzymes of androgen biosynthesis: Cytochrome P45017alpha and 5alpha­steroid reductase. Nat. Prod. Rep. 15, 495-512.
  65. Jung, C. (1997) Structural multiplicity and conformational dynamics in cytochrome P­450. In Trautwein, A.X., Ed. Bioinorganic Chemistry: Transition Metals in Biology and Their Coordination Chemistry. Wiley-VCH, pp. 244-259.
  66. Johnson, E.F. (1992) Mapping determinants of the substrate selectivities of P450 enzymes by site­directed mutagenesis. Trends Pharmacol. Sci. 13, 122-126.
  67. Johnston, J.O., Wright, C.L. and Holbert, G.W. (1995) Enzyme­activated inhibitors of steroidal hydroxylases. J. Steroid Biochem. Mol. Biol. 52, 17-34.
  68. Kalyanaraman, B. (1996) Detection of nitric oxide by electron spin resonance in chemical, photochemical, cellular, physiological, and pathophysiological systems. Methods Enzymol. 268, 168-187.
  69. Kedderis, G.L. (1997) Extrapolation of in vitro enzyme induction data to humans in vivo. Chem. Biol. Interact. 107, 109-121.
  70. Kellner, D.G., Maves, S.A. and Sligar, S.G. (1997) Engineering cytochrome P450s for bioremediation. Curr. Opin. Biotechnol. 8, 274-278.
  71. Keseru, G.M. (1988) Cytochrome P450 catalysed insecticide metabolism: chemical and theoretical models. Sci. Prog. 81, 245-272.
  72. Khatsenko, O. (1998) Interactions between nitric oxide and cytochrome P­450 in the liver. Biochemistry (Moscow) 63, 833-839 (English); Biokhimiia (Moscow) 63, 984-991 (Russian).
  73. Koymans, L., Donne­Op den Kelder, G.M., te Koppele, J.M. and Vermeulen, N.P. (1993) Generalized cytochrome P450-mediated oxidation and oxygenation reactions in aromatic substrates with activated N-H, O-H, C-H, or S-H substituents. Xenobiotica 23, 633-648.
  74. Lambeth, J.D. (1986) Cytochrome P­450scc: A review of the specificity and properties of the cholesterol binding site. Endocr. Res. 12, 371-392.
  75. Lands, W.E. (1998) A review of alcohol clearance in humans. Alcohol 15, 147-160.
  76. Lewis, D.F.V. (1986) Physical methods in the study of the active site geometry of cytochromes P­450. Drug Metab. Rev. 17, 1-66.
  77. Lewis, D.F.V. (1997) Quantitative structure­activity relationships in substrates, inducers, and inhibitors of cytochrome P4501 (CYP1). Drug Metab. Rev. 29, 589-650.
  78. Lewis, D.F.V., Eddershaw, P.J., Dickins, M., Tarbit, M.H. and Goldfarb, P.S. (1998) Structural determinants of cytochrome P450 substrate specificity, binding affinity and catalytic rate. Chem. Biol. Interact. 115, 175-199.
  79. Li, A.P., Maurel, P., Gomez­Lechon, M.J., Cheng, L.C. and Jurima­Romet, M. (1997) Preclinical evaluation of drug-drug interaction potential: Present status of the application of primary human hepatocytes in the evaluation of cytochrome P450 induction. Chem. Biol. Interact. 107, 5-16.
  80. Li, H. and Poulos, T.L. (1994) Structural variation in heme enzymes: a comparative analysis of peroxidase and P450 crystal structures. Structure 2, 461-464.
  81. Lin, J.H. and Lu, A.Y.H. (1998) Inhibition and induction of cytochrome P450 and the clinical implications. Clin. Pharmacokinet. 35, 361-390.
  82. Lindros, K.O. (1997) Zonation of cytochrome P450 expression, drug metabolism and toxicity in liver. Gen. Pharmacol. 28, 191-196.
  83. Livingstone, D.R. (1998) The fate of organic xenobiotics in aquatic ecosystems: quantitative and qualitative differences in biotransformation by invertebrates and fish. Comp. Biochem. Physiol. A 120, 43-49.
  84. Lu, A.Y.H. (1998) The 1996 Bernard B. Brodie lecture. A journey in cytochrome P450 and drug metabolism research. Drug Metab. Dispos. 26, 1168-1173.
  85. McKinnon, R.A. and Nebert, D.W. (1998) Cytochrome P450 knockout mice: new toxicological models. Clin. Exp. Pharmacol. Physiol. 25, 783-787.
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  87. Mansuy, D. and Battioni, P. (1994) Cytochrome P450 model systems. In Sheldon, R.A., Ed. Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, Inc., New York, pp. 99-132.
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  90. Michalets, E.L. (1998) Update: clinically significant cytochrome P­450 drug interactions. Pharmacotherapy 18, 84-112.
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Books

  1. Archakov, A.I. and Bachmanova, G.I. (1990) Cytochrome P­450 and Active Oxygen. Taylor & Francis, London.
  2. Archakov, A.I. and Bachmanova, G.I., Eds. (1992) Cytochrome P­450: Biochemistry and Biophysics. INCO-TNC, Moscow.
  3. Arinç, E., Schenkman, J.B. and Hodgson, E., Eds. (1995) NATO ASI Series, vol. H 90: Molecular Aspects of Oxidative Drug Metabolizing Enzymes. Springer­Verlag, Berlin.
  4. Hutson, D.H., Caldwell, J. and Paulson, G.D., Eds. (1989) Intermediary Xenobiotic Metabolism in Animals: Methodology, Mechanisms and Significance. Taylor & Francis, London.
  5. Ingelman­Sundberg, M., Gustaffson, J.­Å. and Orrenius, S., Eds. (1990) Drug Metabolizing Enzymes: Genetics, Regulation and Toxicology. Stockholm's Projektgrupp AB, Stockholm.
  6. Ioannides, C. (1996) Cytochromes P450: Metabolic and Toxicological Aspects. CRC Press.
  7. Johnson, E.F. and Waterman, M.R., Eds. (1996) Methods Enzymol. 272. Cytochrome P450 (Part B). Academic Press, San Diego.
  8. Kato, R., Estabrook, R.W. and Cayen, M.N., Eds. (1989) Xenobiotic Metabolism and Disposition. Taylor & Francis, London.
  9. Kiel, J.L. (1995) Type­b Cytochromes: Sensors and Switches. CRC Press, Boca Raton.
  10. King, T.E., Mason, H.S. and Morrison, M., Eds. (1988) Oxidases and Related Redox Systems. Liss, New York.
  11. Lechner, M.C., Ed. (1993) Cytochrome P­450: Biochemistry, Biophysics, and Molecular Biology. John Libbey Eurotext, Paris.
  12. Lewis, D.F.V. (1996) Cytochromes P450: Structure, Function and Mechanism. Taylor & Francis, London.
  13. Omura, T., Ishimura, Y. and Fujii­Kuriyama, Y., Eds. (1993) Cytochrome P­450. 2nd Ed., Kodansha, Tokyo.
  14. Ortiz de Montellano, P.R., Ed. (1986) Cytochrome P­450: Structure, Mechanism, and Biochemistry. Plenum Press, New York.
  15. Ortiz de Montellano, P.R., Ed. (1995) Cytochrome P­450: Structure, Mechanism, and Biochemistry. 2nd Ed., Plenum Press, New York.
  16. Phillips, I.R. and Shephard, E.A., Eds. (1998) Methods in Molecular Biology, vol. 107: Cytochrome P450 Protocols. Humana Press, Totowa.
  17. Reddy, C.C., Hamilton, G.A. and Madyastha, K.M., Eds. (1990) Biological Oxidation Systems, vol. 1. Academic Press, San Diego.
  18. Reddy, C.C., Hamilton, G.A. and Madyastha, K.M., Eds. (1990) Biological Oxidation Systems, vol. 2. Academic Press, San Diego.
  19. Ruckpaul, K. and Rein, H., Eds. (1989) Frontiers in Biotransformation, vol. 1: Basis and Mechanisms of Regulation of Cytochrome P­450. Taylor & Francis, London.
  20. Ruckpaul, K. and Rein, H., Eds. (1990) Frontiers in Biotransformation, vol. 2: Principles, Mechanisms and Biological Consequences of Induction. Taylor & Francis, London.
  21. Ruckpaul, K. and Rein, H., Eds. (1990) Frontiers in Biotransformation, vol. 3: Molecular Mechanisms of Adrenal Steroidogenesis and Aspects of Regulation and Application. Taylor & Francis, London.
  22. Ruckpaul, K. and Rein, H., Eds. (1991) Frontiers in Biotransformation, vol. 4: Microbial and Plant Cytochromes P­450: Biochemical Characteristics, Genetic Engineering and Practical Implications. Taylor & Francis, London.
  23. Ruckpaul, K. and Rein, H., Eds. (1991) Frontiers in Biotransformation, vol. 8: Medicinal Implications in Cytochrome P­450 Catalyzed Biotransformations. Akademie Verlag, Berlin.
  24. Sato, R. and Omura, T., Eds. (1978) Cytochrome P­450. Kodansha, Tokyo.
  25. Schenkman, J.B. and Greim, H., Eds. (1993) Cytochrome P450. Springer­Verlag, Berlin.
  26. Schuster, I., Ed. (1989) Cytochrome P­450: Biochemistry and Biophysics. Taylor & Francis, London.
  27. Vereczkey, L. and Magyar, K., Eds. (1985) Cytochrome P­450: Biochemistry, Biophysics and Induction. Akademiai Kiado, Budapest.
  28. Waterman, M.R. and Johnson, E.F., Eds. (1991) Methods Enzymol. 206. Cytochrome P450 (Part A). Academic Press, San Diego.
Bibliography on structural studies of P450s