P450 structures and oxidative metabolism of xenobiotics

Pharmacogenomics

Volumn 4, Issue 4, 2003, Pages 387-395

  Lewis, David F V ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Cytochromes; Drug metabolism; P450 structural models; QSARs

Indexed keywords

BENZODIAZEPINE; CARBOXYLIC ACID; CYTOCHROME P450; CYTOCHROME P450 2B; CYTOCHROME P450 2C; CYTOCHROME P450 2E1; CYTOCHROME P450 3A; CYTOCHROME P450 3A4; CYTOCHROME P450 4A; HALOTHANE; KETOCONAZOLE; N,N DIMETHYLANILINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SODIUM CHANNEL BLOCKING AGENT; TOLUENE; XENOBIOTIC AGENT;

AEROBIC METABOLISM; BIODEGRADATION; BIOREMEDIATION; CALCULATION; CATALYSIS; ELECTRONICS; ENZYME ACTIVITY; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; HUMAN; MAMMAL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RETROSPECTIVE STUDY; REVIEW; SEQUENCE HOMOLOGY; X RAY CRYSTALLOGRAPHY; XENOBIOTIC METABOLISM;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; OXIDATION-REDUCTION; XENOBIOTICS;

MAMMALIA; STAPHYLOCOCCUS PHAGE 3A;

EID: 0038106668     PISSN: 14622416     EISSN: None     Source Type: Journal    
DOI: 10.1517/phgs.4.4.387.22752     Document Type: Review

References (46)

1. Lewis DFV: Cytochromes P450: Structure, Function and Mechanism. Taylor & Francis, London (1996).
2. Lewis DFV: A Guide to Cytochromes P450 Structure and Function. Taylor & Francis, London (2001).
3. Rendic S, DiCarlo FJ: Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers and inhibitors. Drug Metab. Rev. 29, 413-580 (1997).
4. Lewis DFV, Pratt JM: The P450 catalytic cycle and oxygenation mechanism. Drug Metab. Rev. 30, 789-786 (1998).
5. Hlavica P, Lewis DFV: Allosteric phenomena in cytochrome P450-catalyzed monooxygenations. Eur. J. Biochem. 268, 4817-4832 (2001).
6. Lewis DFV, Hlavica P: Interactions between redox partners in various cytochrome P450 systems: functional and structural aspects. Biochimica Biophysica Acta 1280, 1-22 (2000).
7. cam: mutation-induced changes in the proton delivery system. J. Am. Chem. Soc. 121, 10654-10655 (1999).
8. cam: mechanistic implications of EPR and ENDOR studies of catalytic intermediates in native and mutant enzymes. J. Am. Chem. Soc. 123, 1403-1415 (2001).
9. de Groot MJ, Havenith RWA, Vinkers HM, Zwaams R, Vermeulen NPE, van Lenthe JH: Ab initio calculations on iron-porphyrin model systems for intermediates in the oxidative cycle of cytochrome P450s. J. Computer-Aided Mol. Design 12, 183-193 (1998).
10. Segall MD, Payne MC, Ellis SW, Tucker GT, Boyes RN: An ab initio approach to the understanding of cytochrome P450-ligand interactions. Xenobiotica 28, 15-20 (1998).
11. Newcomb M, Shen R, Choi S-Y: Cytochrome P450-catalyzed hydroxylation of mechanistic probes that distinguish between radicals and cations. Evidence for cationic but not for radical intermediates. J. Am. Chem. Soc. 122, 2677-2686 (2000).
12. cam at atomic resolution. Science 287, 1615-1622 (2000).
13. Guengerich FP: Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 14, 611-650 (2001).
14. Coon MJ, Vaz ADN, McGinnity DF, Peng H-M: Multiple activated oxygen species in P450 catalysis. Drug Metabolism Disposition 26, 1190-1193 (1998).
15. Jin S, Makris TM, Bryson TA, Sligar SG, Dawson JH: Epoxidation of olefins by hydroperoxo-ferric cytochrome P450. J. Am. Chem. Soc. 125, 3406-3407 (2003).
16. Ogliaro F, Harris M, Cohen S, Filatov M, de Visser SP, Shaik S: A model 'rebound' mechanism of hydroxylation by cytochrome P450: stepwise and effectively concerted pathways, and their reactivity patterns. J. Am. Chem. Soc. 122, 8977-8989 (2000).
17. de Visser SP, Ogliaro F, Harris N, Shaik S: Multi-state epoxidation of ethene by cytochrome P450: a quantum chemical study. J. Am. Chem. Soc. 123, 3037-3047 (2001).
18. Kubinyi H: QSAR and 3D QSAR in drug design. Part 2: Applications and problems. Drug Discov. Today 2, 538-546 (1997).
19. Lewis DFV: Froniter orbitals in chemical and biological activity: quantitative relationships and mechanstic implications. Drug Metab. Rev. 31, 755-816 (1999).
20. Benigni R, Giuliani A, Franke R, Gruska A: Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines. Chem. Rev. 100, 3697-3714 (2000).
21. Lewis DFV: On the recognition of mammalian microsomal cytochrome P450 substrates and their characteristics. Biochem. Pharmacol. 60, 293-306 (2000).
22. Lewis DFV, Lake BG: Molecular modelling of CYP4A subfamily members based on sequence homology. Xenobiotica 29, 763-781 (1999).
23. Lewis DFV, Dickins M: Factors influencing rates and clearance in P450-mediated reactions: QSARs for substrates of the xenobiotic-metabolizing hepatic microsomal P450s. Toxicology 170, 45-53 (2002).
24. cam. J. Mol. Biol. 195, 687-700 (1987).
25. Ravichandran KG, Boddupalli SS, Hasemann CA, Peterson JA, Deisenhofer J: Crystal structure of hemoprotein domain and P450BM-3, a prototype for microsomal P450s. Science 261, 731-736 (1993).
26. eryF involved in erythromycin biosynthesis. Struct. Biol. 2, 144-153 (1995).
27. terp at 2.3Å resolution. J. Mol. Biol. 236, 1169-1185 (1994).
28. BM-3 haem domain complexed with the fatty acid substrate, palmitoleic acid. Nat. Struct. Biol. 4, 140-146 (1997).
29. Podust LM, Poulos TL, Waterman MR: Crystal structure of cytochrome P450 14a-sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors. Proc. Natl. Acad. Sci. USA 98, 3068-3073 (2001).
30. nor from Fusarium oxysporum. J. Mol. Biol. 239, 158-159 (1994).
31. Williams PA, Cosme J, Sridhar V, Johnson EF, McRee DE: Mammalian cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol. Cell 5, 121-131 (2000).
32. Hasemann CA, Kurumbail RG, Boddupalli SS, Peterson JA, Deisenhofer J: Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure 3, 41-62 (1995).
33. Lewis DFV, Eddershaw PJ, Dickins M, Tarbit MH, Goldfarb PS: Structural determinants of P450 substrate specificity, binding affinity and catalytic rate. Chemico-Biological Interactions 115, 175-199 (1998).
34. Lewis DFV: Homology modelling of human CYP2 family enzymes based on the CYP2C5 crystal structure. Xenobiotica 32, 305-323 (2002).
35. Guengerich FP: Cytochrome P450 enzymes in the generation of commercial products. Nat. Rev. 1, 359-366 (2002).
36. Wiseman A, Lewis DFV, Ridgway T, Wiseman H: Cytochromes P450 enzymes for clean food-processing: limitations of imitations. J. Chem. Technol. Biotechnol. 75, 3-5 (2000).
37. Parton RF, Vankelecom IFJ, Casselman MJA, Bezoukhanova CP, Uytterhoeven JB, Jacobs PA: An efficient mimic of cytochrome P450 from a zeolite-encaged iron complex in a polymer membrane. Nature 370, 541-544 (1994).
38. Eddershaw PJ, Dickins M: Advances in in vitro drug metabolism screening. Pharm. Sci. Technol. Today 2, 13-19 (1999).
39. Guengerich FP: Cytochrome P450 proteins and potential utilization in biodegradation. Environ. Health Perspectives 103(Suppl. 5), 25-28 (1995).
40. Lewis DFV: Structural characteristics of human P450s involved in drug metabolism: QSARs and lipophilicity profiles. Toxicology 144, 197-203 (2000).
41. Poulos TL, Finzel BC, Howard AJ: Crystal structure of substrate-free Pseudomonas putida cytochrome P450. Biochemistry 25, 5314-5322 (1986).
42. BM3. Acta Crystallographica D51, 21-32 (1995).
43. cam tertiary complex. Biochemistry 28, 7586-7592 (1989).
44. cam. Biochemistry 28, 917-922 (1989).
45. cam active site mutant Thr252Ala. Biochemistry 30, 11420-11429 (1991).
46. Sevrioukova IF, Li H, Zhang H, Peterson JA, Poulos TL: Structure of a cytochrome P450-redox partner electron-transfer complex. Proc. Natl. Acad. Sci. USA 96, 1863-1868 (1999).