The Cytochrome P450 Oxidative System

Handbook of Drug Metabolism, Second Edition

Volumn , Issue , 2008, Pages 85-108

  Ortiz de Montellano, Paul R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84876829591     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.3109/9781420076486-7     Document Type: Chapter

References (78)

1. Guengerich FP. Human cytochrome P450 enzymes. In: Ortiz de Montellano PR, ed. Cytochrome P450: Structure, Mechanism, and Biochemistry. 3rd ed. New York: Kluwer/Plenum, 2005:377-530.
2. Nelson, D, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, Gunsalus IC, Nebert DW. P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 1996; 6:1-42.
3. Shimada T, Yamazaki H, Mimura M, Inui Y, Guengerich FP. Interindividual variations in human liver cytochrome P450 enzymes involved in the oxidation of drugs, carcinogens, and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 1994; 270:414-423.
4. Evans WE, Relling MV. Pharmacogenomics: translating function genomics into rational therapeutics. Science 1999; 286:487-491.
5. Nakamura K, Goto F, Ray WA, McAllister CB, Jacqz E., Wilkinson GR, Branch RA. Interethnic differences in genetic polymorphism of debrisoquine and mephenytoin hydroxylation between Japanese and Caucasian populations. Clin Pharmacol Ther 1987; 38:402-408.
6. Kalow W. Genetics of drug transformation. Clin Biochem 1986; 19:76-82.
7. Poulos TL, Finzel BC, Howard AJ. High-resolution crystal structure of cytochrome P450cam. J Mol Biol 1987; 195:687-700.
8. Ravichandran KG, Boddupalli SS, Hasemann CA, Peterson JA, Deisenhofer, J. Crystal structure of hemoprotein domain of P450BM-3, a prototype for microsomal P450s. Science 1993; 261:731-736.
9. Cupp-Vickery JR, Poulos TL. Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Struct Biol 1995; 2:144-153.
10. Williams PA, Cosme J, Sridhar V, Johnson EF, McRee DE. Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol Cell 2000; 5:121-131.
11. Sansen S, Yano JK, Reynald RL, Schoch GA, Griffin KJ, Stout CD, Johnson EF. Adaptations for the oxidation of polycyclic aromatic hydrocarbons exhibited by the structure of human P450 1A2. J Biol Chem 2007; 282:14348-14355.
12. Yano JK, Hsu M, Griffin KJ, Stout CD, Johnson EF. Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen. Nat Struct Mol Biol 2005; 12:822-823.
13. Smith BD, Sanders JL, Porubsky PR, Lushington GH, Stout CD, Scott EE. Structure of the human lung cytochrome P450 2A13. J Biol Chem 2007; 282:17306-17313.
14. Scott EE, He YA, Wester MR, White MA, Chin CC, Halpert JR, Johnson EF, Stout CD. An open conformation of mammalian cytochrome P450 2B4 at 1.6 A ° -resolution. Proc Natl Acad Sci U S A 2003; 100:13196-13201.
15. Schoch GA, Yano YK, Wester MR, Griffin KJ, Stout CD, Johnson EF. Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding-site. J Biol Chem 2004; 279:9497-9503.
16. Williams PA, Cosme J, Ward A, Angove HC, Matak Vinkovic D, Jhoti, H. Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature 2003; 424:464-468.
17. Wester MR, Yano JK, Schoch GA, Yang C, Griffin KJ, Stout CD, Johnson EF. The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-A° resolution. J Biol Chem 2004; 279:35630-35637.
18. Rowland P, Blaney FE, Smyth MG, Jones JJ, Leydon VR, Oxbrow AK, Lewis CJ, Tennant MG, Modi S, Eggleston DS, Chenery RJ, Bridges AM. Crystal structure of human cytochrome P450 2D6. J Biol Chem 2006; 281:7614-7622.
19. Strushkevich NV, Min J, Loppnau P, Tempel W, Arrowsmith CH, Edwards AM, Sundstrom M, Weigelt J, Bochkarev A, Plotnikov AN, Park H. Structural analysis of CYP2R1 in complex with vitamin D. J Mol Biol 380:95-106.
20. Williams PA, Cosme J, Vincovic VM, Ward A, Angove HC, Day PJ, Vonrhein, C., Tickle IJ, Jhoti H. Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science 2004; 305:683-686.
21. Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, Johnson EF. The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05 A ° resolution. J Biol Chem 2004; 279:38091-38094.
22. Atkins WM, Sligar SG. Molecular recognition in cytochrome P450: alteration of regioselective alkane hydroxylation via protein engineering. J Am Chem Soc 1989; 111:2715-2717.
23. Atkins WM, Sligar SG. The roles of active site hydrogen bonding in cytochrome P-450cam as revealed by site-directed mutagenesis. J Biol Chem 1988; 263:18842-18849.
24. Furuya H, Shimizu T, Hirano K, Hatano M, Fujii-Kuriyama Y, Raag R, Poulos TL. Sitedirected mutagenesis of rat liver cytochrome P-450d: catalytic activities toward benzphetamine and 7-ethoxycoumarin. Biochemistry 1989; 28:6848-6857.
25. 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 1992; 267:83-90.
26. Crivori P, Poggesi I. Computational approaches for predicting CYP-related metabolism properties in the screening of new drugs. Eur J Med Chem 2006; 41:795-808.
27. Cruciani G, Carosati E, De Boeck B, Ethirajulu K, Mackie C, Howe T, Vianello R. MetaSite:understanding metabolism in human cytochromes from the perspective of the chemist. J Med Chem 2005; 48:6970-6979.
28. Afzelius L, Arnby CH, Broo A, Carlsson L, Isaksson C, Jurva U, Kjellander B, Kolmodin K, Nilsson K, Raubacher F, Weidolf L. State-of-the-art tools for computational site of metabolism predictions: comparative analysis, mechanistical insights, and future applications. Drug Metab Rev 2007; 39:61-86.
29. Yano YK, Koo LS, Schuller DJ, Li H, Ortiz de Montellano PR, Poulos TL. Crystal structure of a thermophilic cytochrome P450 from the archaeon Sulfolobus solfataricus. J Biol Chem 2000; 275:31086-31092.
30. Scott EE, White MA, He YA, Johnson EF, Stout CD, Halpert JR. Structure of mammalian cytochrome P450 2B4 complexed with 4-(4-chlorophenyl)imidazole at 1.9-A° resolution. J Biol Chem 2004; 279:27294-27301.
31. Schenkman JB, Sligar SG, Cinti DL. Substrate interaction with cytochrome P450. In:Schenkman JB, Kupfer D, eds. Hepatic Cytochrome P-450 Monooxygenase System. New York:Pergamon Press, 1982:587-615.
32. Dawson JH, Sono M. Cytochrome P450 and chloroperoxidase: thiolate-ligated heme enzymes. Spectroscopic determination of their active site structures and mechanistic implications of thiolate ligation. Chem Rev 1987; 87:1255-1276.
33. Sweeney GD, Rothwell JD. Spectroscopic evidence of interaction between 2-allyl-2- isopropylacetamide and cytochrome P-450 of rat liver microsomes. Biochem Biophys Res Commun 1973; 55:798-804.
34. Murataliev MB, Feyereisen R, Walker A. Electron transfer by diflavin reductases. Biochim Biophys Acta-Proteins and Proteomics 2004; 1698:1-26.
35. Wang M, Roberts DL, Paschke R, Shea TM, Masters BS, Kim JJ. Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes. Proc Natl Acad Sci U S A 1997; 94:8411-8416.
36. Schenkman JB, Jansson I. The many roles of cytochrome b5. Pharmacol Ther 2003; 97:139-152.
37. Porter TD. The roles of cytochrome b5 in cytochrome P450 reactions. J Biochem Mol Toxicol 2002; 16:311-316.
38. Yamazaki H, Johnson WW, Ueng JF, Shimada T, Guengerich FP. Lack of electron transfer from cytochrome be in stimulation of catalytic activities of cytochrome P450 3A. Characterization of a reconstituted cytochrome P450 3A4/NADPH-cytochrome P450 reductase system and studies with apo-cytochrome b5. J Biol Chem 1996; 271:27438-27444.
39. Makris TM, Denisov I, Schlichting I, Sligar SG. Activation of molecular oxygen by cytochrome P450. In: Ortiz de Montellano PR, ed. Cytochrome P450: Structure, Mechanism, and Biochemistry New York: Kluwer/Plenum, 2005:149-182.
40. Sligar SG. Coupling of spin, substrate and redox equilibria in cytochrome P-450, Biochemistry 1976; 15:5399-5406.
41. Guengerich FP. Oxidation-reduction properties of rat liver cytochromes P-450 and NADPHcytochrome P-450 reductase related to catalysis in reconstituted systems. Biochemistry 1983; 22:2811-2820.
42. Das A, Grinkova YV, Sligar SG. Redox potential control by drug binding to cytochrome P450 3A4. J Am Chem Soc 2007; 129:13778-13779.
43. Schlichting I, Berendzen J, Chu K, Stock AM, Maves SA, Benson DE, Sweet RM, Ringe D, Pesko GA, Sligar SG. The catalytic pathway of cytochrome P450cam at atomic resolution. Science 2000; 287:1615-1622.
44. Ortiz de Montellano PR, De Voss JJ. Substrate oxidation by cytochrome P450 enzymes. In:Ortiz de Montellano PR, ed. Cytochrome P450: Structure, Mechanism, and Biochemistry, New York: Kluwer/Plenum, 2005:183-245.
45. Vaz A, McGinnity D, Coon M. Epoxidation of olefins by cytochrome P450: evidence from sitespecific mutagenesis for hydroperoxo-iron as an electrophilic oxidant. Proc Nat Acad Sci USA 1998; 95:3555-3560.
46. Oguri K, Tanimoto Y, Yoshimura H. Metabolite fate of strychnine in rats. Xenobiotica 1989; 19:171-178.
47. Hjelmeland LM, Aronow L, Trudell JR. Intramolecular determination of primary kinetic isotope effects in hydroxylations catalyzed by cytochrome P-450. Biochem Biophys Res Commun 1977; 76:541-549.
48. Foster AB. Deuterium isotope effects in the metabolism of drugs and xenobiotics: implications for drug design. Adv Drug Res 1985; 14:2-40.
49. Frommer U, Ullrich V, Staudinger H. Hydroxylation of aliphatic compounds by liver microsomes. 1. The distribution of isomeric alcohols. Hoppe Seylers Z Physiol Chem 1970; 351:903-912.
50. Shaik S, Visser SP. Computational approaches to cytochrome P450 function. In: Ortiz de Montellano PR, ed. Cytochrome P450: Structure, Mechanism, and Biochemistry. New York:Kluwer/Plenum, 2005:45-85.
51. Groves JT, McClusky GA, White RE, Coon MJ. Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate. Biochem Biophys Res Commun 1978; 81:154-160.
52. Hefner J, Rubenstein SM, Ketchum RE, Gibson DM, Williams RM, Croteau R. Cytochrome P450-catalyzed hydroxylation of taxa-4(5), 11(12)-diene to taxa-4(20), 11(12)dien-5a-ol: the first oxygenation step in taxol biosynthesis. Chem Biol 1996; 3:479-489.
53. Ortiz de Montellano PR, Stearns RA. Timing of the radical recombination step in cytochrome P-450 catalysis with ring-strained probes. J Am Chem Soc 1987; 109:3415-3420.
54. Newcomb M, Hollenberg PF, Coon MJ. Multiple mechanisms and multiple oxidants in P450- catalyzed hydroxylations. Arch Biochem Biophys 2003; 409:72-79.
55. Jiang Y, He X, Ortiz de Montellano PR. Radical intermediates in the catalytic oxidation of hydrocarbons by bacterial and human cytochrome P450 enzymes. Biochemistry 2006; 45:533-542.
56. Hinson JA, Mitchell JR, Jollow DJ. N-Hydroxylation of p-chloroacetanilide in hamsters. Biochem Pharmacol 1975; 25:599-601.
57. Ortiz de Montellano PR, Mangold BLK, Wheeler C, Wheeler C, Kunze KL, Reich NO. Stereochemistry of cytochrome P-450 catalyzed epoxidation and prosthetic heme alkylation. J Biol Chem 1983; 258:4208-4213.
58. Harvey DJ, Glazener L, Johnson DB, Butler CM, Horning MG. Comparative metabolism of four allylic barbiturates and hexobarbital by rat and guinea pig. Drug Metab Dispos 1977; 5:527-546.
59. Miller RE, Guengerich FP. Oxidation of trichloroethylene by liver microsomal cytochrome P-450: evidence for chlorine migration in a transition state not involving trichloroethylene oxide. Biochemistry 1982; 21:1090-1097.
60. Correia MA, Ortiz de Montellano PR. Inhibition of cytochrome P450 enzymes. In: Ortiz de Montellano PR, ed. Cytochrome P450: Structure, Mechanism, and Biochemistry. New York:Kluwer/Plenum, 2005:247-322.
61. Kunze KL, Mangold BLK, Wheeler C, Beilan HS, Ortiz de Montellano PR. The cytochrome P-450 active site. Regiospecificity of the prosthetic heme alkylation by olefins and acetylenes. J Biol Chem 1983; 258:4202-4207.
62. Jerina DM, Daly JW. Arene oxides: a new aspect of drug metabolism. Science 1974; 185:573-582.
63. Barker SA, Hsieh LC, McDowell TR, Short CR. Short, qualitative and quantitative analysis of the anthelminthic febendazole and its metabolites in biological matrices by direct exposure probe mass spectrometry. Biomed Environ Mass Spectrom 1987; 14:161-165.
64. Den Besten, C, van Bladeren PJ, Duizer E, Vervoort J, Rietjens IM. Cytochrome P450-mediated oxidation of pentafluorophenol to tetrafluorobenzoquinone as the primary reaction product. Chem Res Toxicol 1993; 6:674-680.
65. He X, Cryle MJ, De Voss JJ, Ortiz de Montellano PR. Calibration of the channel that determines the o-hydroxylation regiospecificity of cytochrome P4504A. Catalytic oxidation of 12-halododecanoic acids. J Biol Chem 2005; 280:22697-22705.
66. Seto Y, Guengerich FP. Partitioning between N-dealkylation and N-oxygenation in the oxidation of N, N-dialkylarylamines catalyzed by cytochrome P450 2B1. J Biol Chem 1993; 268:9986-9997.
67. Karki SB, Dinnocenzo JP, Jones JP, Korzekwa KR. Mechanism of oxidative amine dealkylation of substituted N, N-dimethylanilines by cytochrome P-450: application of isotope effect profiles. J Am Chem Soc 1995; 117:3657-3664.
68. Kammerer B, Scheible H, Albrecht W, Bleiter CH, Laufer S. Pharmacokinetics of ML3403 {4-[5-(4-fluorophenyl)-2-methylsulfanyl-3H-imidazol-4-yl]pyridine-2-yl}-(1-phenylethyl)-amine, a 4-pyridinylimidazole-type p38 mitogen-activated protein kinase inhibitor. Drug Metab Dispos 2007; 35:875-883.
69. Madan A, Williams TD, Faiman MD. Glutathione- and glutathione-S-transferase-dependent oxidative desulfuration of the thione xenobiotic diethyldithiocarbamate methyl ester. Mol Pharmacol 1994; 46:1217-1225.
70. Rettie AE, Boberg M, Rettenmeier AW, Baillie TA. Cytochrome P-450-catalyzed desaturation of valproic acid in vitro. Species differences, induction effects, and mechanistic studies. J Biol Chem 1988; 263:13733-13738.
71. Korzekwa KR, Trager WF, Nagata K, Parkinson A, Gillette JR. Isotope effect studies on the mechanism of the cytochrome P450IIA1-catalyzed formation of D6-testosterone from testosterone. Drug Metab Dispos 1990; 18:974-979.
72. Vyas KP, Kari PH, Prakash SR, Duggan DE. B. Biotransformation of lovastatin. II. In vitro metabolism by rat and mouse liver microsomes and involvement of cytochrome P-450 in dehydrogenation of lovastatin. Drug Metab Dispos 1990; 18:218-222.
73. Stearns RA, Chakravarty PK, Chen R, Chiu SH. Biotransformation of losartan to its active carboxylic acid metabolite in human liver microsome. Role of cytochrome P4502C and 3A subfamily members. Drug Metab Dispos 1995; 23:207-215.
74. Roberts ES, Vaz AD, Coon MJ. Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: deformylation with olefin formation. Proc Natl Acad Sci U S A 1991; 88:8963-8966.
75. Akhtar M, Njar VCO, Wright JN. Mechanistic studies on aromatase and related C__C bond cleaving P-450 enzymes. J Steroid Biochem Molec Biol 1993; 44:375-387.
76. Goeptar AR, Scheerens H, Vermeulen NPE. Oxygen and xenobiotic reductase activities of cytochrome P450. Crit Rev Toxicol 1995; 25:25-65.
77. Patterson LH. Bioreductively activated antitumor N-oxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy. Drug Metab Rev 2002; 34:581-592.
78. Saunders MP, Patterson AV, Chinje EC, Harris AL, Stratford IJ. NADPH:cytochrome c (P450) reductase activates tirapazamine (SR4233) to restore hypoxic and oxic cytotoxicity in anaerobic resistant derivative of the A549 lung cancer cell line. Br J Cancer 2000; 82:651-656.