Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenases

Biochemical and Biophysical Research Communications

Volumn 338, Issue 1, 2005, Pages 331-336

  Johnson, Eric F ^a   Stout, C David ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

CYP2A6; CYP2C8; CYP2C9; CYP3A4; Cytochrome P450; Drug metabolism; Monooxygenase; Structure

Indexed keywords

BENZBROMARONE; CYCLOSPORIN; CYTOCHROME P450 2A6; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 3A4; DAPSONE; ERYTHROMYCIN; FLURBIPROFEN; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; MIDAZOLAM; MONTELUKAST; NIFEDIPINE; NONSTEROID ANTIINFLAMMATORY AGENT; PACLITAXEL DERIVATIVE; PHENYTOIN; TESTOSTERONE; TROGLITAZONE; WARFARIN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; COMPLEX FORMATION; DRUG METABOLISM; DRUG OXIDATION; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; GENE EXPRESSION; HUMAN; NONHUMAN; PRIORITY JOURNAL; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE; PROTEIN TERTIARY STRUCTURE; REVIEW; SEQUENCE ALIGNMENT; SPECIES DIFFERENCE; XENOBIOTIC METABOLISM;

AMINO ACID SEQUENCE; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; XENOBIOTICS;

EID: 27544516024     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.08.190     Document Type: Review

References (26)

1. D.R. Nelson, D.C. Zeldin, S.M. Hoffman, L.J. Maltais, H.M. Wain, and D.W. Nebert Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants Pharmacogenetics 14 2004 1 18
2. F.P. Guengerich Human cytochrome P450 enzymes P.R. Ortiz de Montellano Cytochrome P450: Structure mechanism and biochemistry 2005 Kluwer Academic/Plenum Publishers New York 377 530 This is a recent, comprehensive review of the human CYPs with an extensive bibliography
3. J.K. Yano, M.R. Wester, G.A. Schoch, K.J. Griffin, C.D. Stout, and E.F. Johnson The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05-Å resolution J. Biol. Chem. 279 2004 38091 38094
4. P.A. Williams, J. Cosme, D.M. Vinkovic, A. Ward, H.C. Angove, P.J. Day, C. Vonrhein, I.J. Tickle, and H. Jhoti Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone Science 305 2004 683 686
5. P.A. Williams, J. Cosme, A. Ward, H.C. Angove, V.D. Matak, and H. Jhoti Crystal structure of human cytochrome P450 2C9 with bound warfarin Nature 424 2003 464 468
6. M.R. Wester, J.K. Yano, G.A. Schoch, C. Yang, K.J. Griffin, C.D. Stout, and E.F. Johnson The structure of human microsomal cytochrome P450 2C9 complexed with flurbiprofen at 2.0 Å resolution J. Biol. Chem. 279 2004 35630 35637
7. G.A. Schoch, J.K. Yano, M.R. Wester, K.J. Griffin, C.D. Stout, and E.F. Johnson Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding site J. Biol. Chem. 279 2004 9497 9503
8. J.K. Yano, M.H. Hsu, K.J. Griffin, C.D. Stout, and E.F. Johnson Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen Nat. Struct. Mol. Biol. 2005 Available online ahead of the printed version
9. T.L. Poulos, and E.F. Johnson Structures of cytochrome P450 enzymes P.R. Ortiz de Montellano Cytochrome P450: Structure, Mechanism, and Biochemistry third ed. 2005 Kluwer Academic/Plenum Publishers New York 87 114
10. T.L. Poulos, B.C. Finzel, I.C. Gunsalus, G.C. Wagner, and J. Kraut 2.6 Angstrom crystal structure of the Pseudomonas putida cytochrome P-450 J. Biol. Chem. 260 1985 16122 16130
11. P.A. Williams, J. Cosme, V. Sridhar, E.F. Johnson, and D.E. McRee The crystallographic structure of a mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity Mol. Cell 5 2000 121 132
12. S. Izumi, H. Kaneko, T. Yamazaki, T. Hirata, and S. Kominami Membrane topology of guinea pig cytochrome P450 17 alpha revealed by a combination of chemical modifications and mass spectrometry Biochemistry 42 2003 14663 14669
13. H. Deng, J. Wu, S.P. So, and K.H. Ruan Identification of the residues in the helix F/G loop important to catalytic function of membrane-bound prostacyclin synthase Biochemistry 42 2003 5609 5617
14. M.J. Headlam, M.C. Wilce, and R.C. Tuckey The F-G loop region of cytochrome P450scc (CYP11A1) interacts with the phospholipid membrane Biochim. Biophys. Acta 1617 2003 96 108
15. J. Mestres Structure conservation in cytochromes P450 Proteins 58 2005 596 609
16. O. Gotoh 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
17. K.R. Korzekwa, N. Krishnamachary, M. Shou, A. Ogai, R.A. Parise, A.E. Rettie, F.J. Gonzalez, and T.S. Tracy Evaluation of atypical cytochrome P450 kinetics with two- substrate models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites Biochemistry 37 1998 4137 4147
18. W.M. Atkins Non-Michaelis-Menten kinetics in cytochrome P450-catalyzed reactions Annu. Rev. Pharmacol. Toxicol. 45 2005 291 310
19. M.J. Dabrowski, M.L. Schrag, L.C. Wienkers, and W.M. Atkins Pyrene-pyrene complexes at the active site of cytochrome P450 3A4: evidence for a multiple substrate binding site J. Am. Chem. Soc. 124 2002 11866 11867
20. S.M. Hoffman, D.R. Nelson, and D.S. Keeney Organization, structure and evolution of the CYP2 gene cluster on human chromosome 19 Pharmacogenetics 11 2001 687 698
21. R.A. Totah, and A.E. Rettie Cytochrome P450 2C8: substrates, inhibitors, pharmacogenetics, and clinical relevance Clin. Pharmacol. Ther. 77 2005 341 352
22. A.E. Rettie, and J.P. Jones Clinical and toxicological relevance of CYP2C9: drug-drug interactions and pharmacogenetics Annu. Rev. Pharmacol. Toxicol. 45 2005 477 494
23. R.L. Walsky, R.S. Obach, E.A. Gaman, J.P. Gleesen, and W.R. Proctor Selective inhibition of human cytochrome P450 2C8 by montelukast Drug Metab. Dispos. 33 2005 413 418
24. J.M. Hutzler, M.J. Hauer, and T.S. Tracy Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model Drug Metab. Dispos. 29 2001 1029 1034
25. P.J. Kraulis MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures J. Appl. Cryst. 24 1991 946 950
26. G.J. Kleywert, and T.A. Jones Detection, delineation, measurement and display of cavities in macromolecular structures Acta Cryst. D 50 1994 178 185