How do azoles inhibit cytochrome P450 enzymes? A density functional study

Journal of Physical Chemistry A

Volumn 112, Issue 50, 2008, Pages 12911-12918

  Balding, Philip R ^a,b   Porro, Cristina S ^a,b   McLean, Kirsty J ^a   Sutcliffe, Michael J ^a,b   Maréchal, Jean Didier ^a,c   Munro, Andrew W ^a   De Visser, Sam P ^a,b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

A DENSITIES; ACTIVE SITES; BINDING MECHANISMS; CATALYTIC CYCLES; CATALYTIC FUNCTIONS; CHEMICAL EQUILIBRIUMS; DENSITY FUNCTIONAL STUDIES; ETHANOL MOLECULES; FLUCONAZOLE; HEME IRONS; INHIBITOR MOLECULES; OXYGEN BINDINGS; PENTA COORDINATED; REACTION MECHANISMS; RELATIVE ENERGIES; SPIN STATES; STEPWISE MECHANISMS; STRUCTURAL MOTIFS; STRUCTURAL STUDIES; SUBSTRATE OXIDATIONS; WATER MOLECULES;

BINDING ENERGY; CATALYSTS; CATALYTIC OXIDATION; COORDINATION REACTIONS; DENSITY FUNCTIONAL THEORY; ENZYMES; ETHANOL; HEMOGLOBIN; HYDROGEN; HYDROGEN BONDS; MODEL STRUCTURES; MOLECULES; OXYGEN; PHASE EQUILIBRIA; PORPHYRINS; PROTEINS; SPIN DYNAMICS;

BINDING SITES;

CAMPHOR; CYTOCHROME P450; ENZYME INHIBITOR; FLUCONAZOLE; HEME; METYRAPONE; PYRROLE DERIVATIVE; WATER;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; ENZYME ACTIVE SITE; ENZYMOLOGY; HUMAN; KINETICS; LIVER; METABOLISM; PROTEIN CONFORMATION;

AZOLES; BINDING SITES; CAMPHOR; CATALYTIC DOMAIN; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; FLUCONAZOLE; HEME; HUMANS; KINETICS; LIVER; METYRAPONE; MODELS, MOLECULAR; PROTEIN CONFORMATION; WATER;

EID: 58149173952     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp802087w     Document Type: Article

References (76)

1. (a) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
2. (b) Ortiz de Montellano, P. R., Ed. Cytochrome P450: Structure, Mechanism and Biochemistry, 3rd ed.; Kluwer Academic/Plenum Publishers: New York, 2004.
3. (c) Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104,. 3947-3980.
4. (d) Denisov, I. G.; Makris, T. M.; Sligar, S. G.; Schlichting, I. Chem. Rev. 2005, 105,. 2253-2277.
5. (e)Groves, J. T. J. Inorg. Biochem. 2006, 100, 434-447.
6. (a) Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611-650.
7. (b)Ortiz de Montellano, P. R.; De Voss, J. J. Substrate Oxidation by Cytochrome P450 Enzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers; New York, 2004; Chapter 6, pp 183-245.
8. Guengerich, F. P. Drug Metab. Rev. 2004, 36, 159-197.
9. (a) Guengerich, F. P. Annu. Rev. Pharmacol. Toxicol. 1999, 39, 1-17.
10. (b) Guengerich, F. P. Human Cytochrome P450 Enzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers: New York. 2004; Chapter 10, pp 377-530.
11. Capdevila, J. H.; Falck, J. R.; Imig, J. D. Kidney Int. 2007, 72, 683-689.
12. Odds, F. C.; Brown, A. J.; Gow, N. A. Trends Microbiol. 2003, 11, 272-279.
13. Feyereisen, R. Biochem. Soc. Trans. 2006, 34, 1252-1255.
14. Cole, S. T. Microbiology 2002, 148, 2919-2928.
15. McLean, K. J.; Dunford. A. J.; Neeli, R.; Driscoll, M. D.; Munro, A. W. Arch. Biochem. Biophys. 2007, 464, 228-240.
16. McLean, K. J.; Warman, A. J.; Seward, H. E.; Marshall, K. R.; Girvan, H. M.; Cheesman, M. R.; Waterman, M. R.; Munro, A. W. Biochemistry 2006, 45,. 8427-8443.
17. Hollenberg, P. F. Drug Metab. Rev. 2002, 34, 17-35.
18. (a) Ferslew, K. E.; Hagardorn, A. N.; Harlan, G. C.; McCormick. W. F. J. Forensic Sci 1998, 43, 1082-1085.
19. (b) Kudo, K.; Imamura, T.; Jitsufuchi, N.; Zhang, X. X.; Tokunaga, H.; Nagata, T. Forensic Sci. Int. 1997, 86, 35-41.
20. Temple, T. E.; Liddle. G. W. Anna. Rev. Pharmacol. Toxicol. 1970, 10, 199-218.
21. Zhang, W.; Ramamoorthy, Y.; Kilicarslan, T.; Nolte, H.; Tvndale. R. F.; Sellers, E. M. Drug Metab. Dispos. 2002, 30, 314-318.
22. Ahmad, Z.; Sharma, S.; Khuller, G. K. FEMS Microbiol. Lett. 2006, 262, 181-186.
23. Schenkman, J. B.; Remmer, H.; Estabrook, R. W. Mol. Pharmacol. 1967, 3, 113-123.
24. Van den Bossche, H. Curr. Top. Med. Mycol. 1985, 1, 313-351.
25. Schuster, I. Xenobiotica 1985, 15, 529-546.
26. (a) Varhe, A.; Olkkola, K. T.; Neuvonen, P. J. Clin. Pharmacol. Ther. 1994, 56, 601-607.
27. (b) Park, J. Y.; Shon, J. H.; Kim, K. A.; Jung, H. J.; Shim, J. C.; Yoon, Y. R.; Cha, I. J.; Shin, J. G. J. din. Psychopharmacol. 2006, 26, 135-142.
28. (c) Murayama, N.; Imai, N.; Nakane, T.; Shimizu, M.; Yamazaki, H. Biochem. Pharmacol. 2007, 73, 2020-2026.
29. (a) Guardiola-Diaz, H. M.; Foster, L. A.; Mushrush, D.; Vaz, A. D. Biochem. Pharmacol. 2001, 61, 1463-1470.
30. (b) McLean, K. J.; Cheesman, M. R.; Rivers, S. L.; Richmond, A.; Leys, D.; Chapman, S. K.; Reid, G. A.; Price, N. C.; Kelly, S. M.; Clarkson, J.; Smith, W. E.; Munro, A. W. J. Inorg. Biochem. 2002, 97, 527-541.
31. (c) Banfi, E.; Scialino, G.; Zampieri, D.; Mamolo, M. G.; Vio, L.; Ferrone, M.; Fermeglia, M.; Paneni, M. S.; Pricl, S. J. Antimicrob. Chemoth. 2006, 58, 76-84.
32. (a) Poulos, T. L.; Howard, A. J. Biochemistry 1987, 26, 8165-8174.
33. (b) Podust, L. M.; Poulos, T. L.; Waterman, M. R. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 3068-3073.
34. (a) Cupp-Vickery, J. R.; Garcia, C.; Hofacre, A.; McGee-Estrada, K. J. Mol. Biol. 2001, 311, 101-110.
35. (b) Verras, A.; Alian, A.; Ortiz de Montellano, P. R. Protein Eng., Des. Sel. 2006, 19, 491-496.
36. (c) Ekroos, M.; Sjogren, T. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13682-13687.
37. Seward, H. E.; Roujeinikova, A.; McLean, K. J.; Munro, A. W.; Leys, D. J. Biol. Chem. 2006, 281, 39437-39443. '
38. Gorren, A. C. F.; Schmidt, K.; Mayer, B. Biochemistry 2002, 41, 7819-7829.
39. (a) Das. A.; Grinkova, Y. V.; Sligar. S. G. J. Am. Chem. Soc. 2007, 129, 13778-13779.
40. (b) Denisov, I. G.; Grinkova, Y. V.; McLean, M. A.; Sligar, S. G. J. Biol. Chem. 2007, 282, 26865-26873.
41. Poulos, T.L.; Raag, R. FASEB J. 1992, 6, 674-679.
42. Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, R. M.; Ringe, D.; Petsko, G. A.; Sligar, S. G. Science 2000, 287, 1615-1622.
43. (a) Dawson, J. H.; Holm, R. H.; Trudell, J. R.; Barth, G.; Linder, R. E.; Bunnenberg, E.; Djerassi, C.; Tang, S. C. J. Am. Chem. Soc. 1976, 98, 3707-3709.
44. (b) Poulos, T. L. J. Biol. Inorg. Chem. 1996, 1, 356-359.
45. (c) Shaik. S.: Kumar, D.: de Visser, S. P.; Altun. A.; Thiel, W. Chem. Rev. 2005, 105, 2279-2328.
46. (a) Paine, M. J. I.; Scrutton, N. S.; Munro, A. W.; Gutierez, A.; Roberts, G. C. K.; Wolf, C. R. Electron Transfer Partners of Cytochrome P450. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers: New York, 2004; Chapter 4, pp 115-148.
47. (b) Warman, A. J.; Roitel, O.; Neeli, R.; Girvan, H. M.; Seward, H. E.; Murray, S. A.; McLean, K. J.; Joyce. M. G.; Toogood, H.; Holt, R. A.; Leys, D.; Scrutton. N. S.; Munro, A. W. Biochem. Soc. Trans. 2005, 33, 747-753.
48. (a) Green, M. T. J. Am. Chem. Soc. 2000, 722, 9495-9499.
49. (b) de Visser, S. P.; Shaik, S.; Sharma, P. K.; Kumar, D.; Thiel, W. J. Am. Chem. Soc. 2003, 125, 15779-15788.
50. (c) Rydberg, P.; Sigfridsson, E.; Ryde, U. J. Biol. Inorg. Chem. 2004, 9, 203-223.
51. (d) Derat, E.; Shaik, S. J. Am. Chem. Soc. 2006, 728, 8185-8198.
52. (e) Groenhof, A. E.; Swart, M.; Ehlers, A. W.: Lammertsma, K. J. Phys. Chem. A 2005, 109,. 3411-3417.
53. (a) de Visser, S. P. J. Am. Chem. Soc. 2006, 128, 9813-9824.
54. (b)de Visser, S. P. J. Am. Chem. Soc. 2006, 128, 15809-15818.
55. (c) Aluri, S.; de Visser, S. P. J. Am. Chem. Soc. 2007, 129, 14846-14847.
56. Frisch, M. J. Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.: Kitao, O.; Nakai, H.; Klene, M.: Li. X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Oehterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski. J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz. P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian. Inc.: Wallingford. CT. 2003.
57. (a) Becke. A. D. J. Chem. Phys. 1993, 98,. 5648-5652.
58. (b) Lee. C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
59. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
60. (b) Perdew. J. P. Phys. Rev. B 1986, 33, 8822-8824.
61. Hay, P. J.; Wadt. W. R. J. Chem. Phys. 1985, 82,. 270-283.
62. Jaguar 7.0; Schrodinger, LLC.: New York, NY, 2007.
63. Ogliaro, F.; Cohen, S.; de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122,. 12892-12893.
64. (a) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. Angew. Chem., Int. Ed 2002, 41, 1947-1951.
65. (b) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. J. Am. Chem. Soc. 2002, 124, 11809-11826.
66. (c)de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2003, 125,. 7413-7424.
67. (d) de Visser, S. P. Chem.-Eur. J. 2006, 12, 8168-8177.
68. Thomann, H.: Bernardo, M.; Goldfarb, D.: Kroneck. P. M. H.: Ullrich, V. J. Am. Chem. Soc. 1995, 117, 8243-8251.
69. (a) Green, M. T. J. Am. Chem. Soc. 1998, 120, 10772-10773.
70. (b)Filatov, M.; Harris, N.; Shaik, S. J. Chem. Soc., Perkin Trans. 2 1999, 3, 399-411.
71. (c) Schoneboom, J. C.; Thiel, W. J. Phys. Chem. B 2004, 108, 7468-7478.
72. Zhao, Y. H.; White. M. A.; Muralidhara, B. K.; Sun. L.; Halpert. J. R.; Stout. C. D. J. Biol. Chem. 2006, 281,. 5973-5981.
73. de Visser, S. P. J. Phys. Chem. A 2005, 109, 11050-11057.
74. de Visser. S. P.; Ogliaro, F.; Gross. Z.; Shaik. S. Chem.-Eur. J. 2001, 7, 4954-4960.
75. (a) Sligar, S. G. Biochemisty 1976, 15, 5399-5406.
76. (b) Auclair, K.; Moenne-Loccoz, P.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 2001, 123, 4877-4885.