Spectra and kinetic studies of the Compound I derivative of cytochrome P450 119

Journal of the American Chemical Society

Volumn 130, Issue 40, 2008, Pages 13310-13320

  Sheng, Xin ^a   Horner, John H ^a   Newcomb, Martin ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPOUND I; CYTOCHROME P-450; KINETIC STUDIES; LASER-FLASH PHOTOLYSIS; OVERLAPPING TRANSITIONS; PEROXYNITRITE; SORET BANDS; UV-VIS SPECTRUM;

PHOTOLYSIS;

10 UNDECENOIC ACID; BENZYL ALCOHOL; CARBON; CHLORIDE PEROXIDASE; CYTOCHROME P450; CYTOCHROME P450 119; ETHYLBENZENE; HEME; HYDROGEN; HYDROGEN PEROXIDE; IRON DERIVATIVE; LAURIC ACID; OXYGEN 18; PEROXYNITRITE; PORPHYRIN; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; EPOXIDATION; HYDROXYLATION; NONHUMAN; OXIDATION; PHOTOLYSIS; PHOTOOXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE; SIMULATION; ULTRAVIOLET SPECTROSCOPY;

ARCHAEAL PROTEINS; CYTOCHROME P-450 ENZYME SYSTEM; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEROXYNITROUS ACID; PHOTOLYSIS; SPECTROPHOTOMETRY; SUBSTRATE SPECIFICITY; SULFOLOBUS SOLFATARICUS;

EID: 53549099423     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802652b     Document Type: Article

References (63)

1. Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer: New York, 2005.
2. Guengerich, F. P. In Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer: New York, 2005; pp 377-530.
3. Scripture, C. D.; Sparreboom, A.; Figg, W. D. Lancet Oncol. 2005, 6, 780-789.
4. Rodriguez-Antona, C.; Ingelman-Sundberg, M. Oncogene 2006, 25, 1679-1691.
5. Lieber, C. S. Drug Metab. Rev. 2004, 36, 511-529.
6. Dawson, J. H. Science 1988, 240, 433-439.
7. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
8. Groves, J. T. In Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer: New York, 2005; pp 1-43.
9. Makris, T. M.; Denisov, I.; Schlichting, I.; Sligar, S. G. In Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer: New York, 2005; pp 149-182.
10. Ortiz de Montellano, P. R.; De Voss, J. J. In Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer: New York, 2005; pp 183-245.
11. Davydov, R.; Macdonald, I. D. G.; Makris, T. M.; Sligar, S. G.; Hoffman, B. M. J. Am. Chem. Soc. 1999, 121, 10654-10655.
12. Davydov, R.; Makris, T. M.; Kofman, V.; Werst, D. E.; Sligar, S. G.; Hoffman, B. M. J. Am. Chem. Soc. 2001, 123, 1403-1415.
13. Coon, M. J.; Blake, R. C., II; Oprian, D. D.; Ballou, D. P. Acta Biol. Med. Ger. 1979, 38, 449-458.
14. Egawa, T.; Shimada, H.; Ishimura, Y. Biochem. Biophys. Res. Commun. 1994, 201, 1464-1469.
15. Spolitak, T.; Dawson, J. H.; Ballou, D. P. J. Biol. Chem. 2005, 280, 20300-20309.
16. Schunemann, V.; Jung, C.; Terner, J.; Trautwein, A. X.; Weiss, R. J. Inorg. Biochem. 2002, 91, 586-596.
17. Schunemann, V.; Trautwein, A. X.; Jung, C.; Terner, J. Hyperfine Interact. 2002, 141, 279-284.
18. Schunemann, V.; Lendzian, F.; Jung, C.; Contzen, J.; Barra, A. L.; Sligar, S. G.; Trautwein, A. X. J. Biol. Chem. 2004, 279, 10919-10930.
19. Jung, C.; Schunemann, V.; Lendzian, F.; Trautwein, A. X.; Contzen, J.; Galander, M.; Bottger, L. H.; Richter, M.; Barra, A. L. Biol. Chem. 2005, 386, 1043-1053.
20. Kellner, D. G.; Hung, S. C.; Weiss, K. E.; Sligar, S. G. J. Biol. Chem. 2002, 277, 9641-9644.
21. Zhang, R.; Chandrasena, R. E. P.; Martinez, E., II.; Horner, J. H.; Newcomb, M. Org. Lett. 2005, 7, 1193-1195.
22. Newcomb, M.; Zhang, R.; Chandrasena, R. E. P.; Halgrimson, J. A.; Horner, J. H.; Makris, T. M.; Sligar, S. G. J. Am. Chem. Soc. 2006, 128, 4580-4581.
23. McLean, M. A.; Maves, S. A.; Weiss, K. E.; Krepich, S.; Sligar, S. G. Biochem. Biophys. Res. Commun. 1998, 252, 166-172.
24. Maves, S. A.; Sligar, S. G. Protein Sci. 2001, 10, 161-168.
25. Rabe, K. S.; Kiko, K.; Niemeyer, C. M. ChemBioChem 2008, 9, 420-425.
26. Daiber, A.; Herold, S.; Schöneich, C.; Namgaladze, D.; Peterson, J. A.; Ullrich, V. Eur. J. Biochem. 2000, 267, 6729-6739.
27. Floris, R.; Piersma, S. R.; Yang, G.; Johnes, P.; Wever, R. Eur. J. Biochem. 1993, 215, 767-775.
28. Mehl, M.; Daiber, A.; Herold, S.; Shoun, H.; Ullrich, V. Nitric Oxide 1999, 3, 142-152.
29. Exner, M.; Herold, S. Chem. Res. Toxicol. 2000, 13, 287-293.
30. Boccini, F.; Herold, S. Biochemistry 2004, 43, 16393-16404.
31. Furtmüller, P, G.; Jantschko, W.; Zederbauer, M.; Schwanninger, M.; Jakopitsch, C.; Herold, S.; Koppenol, W. H.; Obinger, C. Biochem. Biophys. Res. Commun. 2005, 337, 944-954.
32. Gebicka, L.; Didik, J. J. Inorg. Biochem. 2007, 101, 159-164.
33. Behan, R. K.; Hoffart, L. M.; Stone, K. L.; Krebs, C.; Green, M. T. J. Am. Chem. Soc. 2007, 129, 5855-5859.
34. Newcomb, M.; Halgrimson, J. A.; Horner, J. H.; Wasinger, E. C.; Chen, L. X.; Sligar, S. G. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 8179-8184.
35. Stone, K. L.; Behan, R. K.; Green, M. T. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 16563-16565.
36. Bolzan, R. M.; Cueto, R.; Squadrito, G. L.; Uppu, R. M.; Pryor, W. A. Methods Enzymol. 1999, 301, 178-187.
37. Kissner, R.; Koppenol, W. H. J. Am. Chem. Soc. 2002, 124, 234-239.
38. Kirsch, M.; Korth, H. G.; Wensing, A.; Sustmann, R.; de Groot, H. Arch. Biochem. Biophys. 2003, 418, 133-150.
39. Goldstein, S.; Lind, J.; Merényi, G. Chem. Rev. 2005, 105, 2457-2470.
40. Makris, T. M.; von Koenig, K.; Schlichting, I.; Sligar, S. G. J. Inorg. Biochem. 2006, 100, 507-518.
41. Palcic, M. M.; Rutter, R.; Araiso, T.; Hager, L. P.; Dunford, H. B. Biochem. Biophys. Res. Commun. 1980, 94, 1123-1127.
42. Egawa, T.; Proshlyakov, D. A.; Miki, H.; Makino, R.; Ogura, T.; Kitagawa, T.; Ishimura, Y. J. Biol. Inorg. Chem. 2001, 6, 46-54.
43. Zhang, R.; Nagraj, N.; Lansakara, D. S. P.; Hager, L. P.; Newcomb, M. Org. Lett. 2006, 8, 2731-2734.
44. In the initial communication of this work (ref 22), we reported that lauric acid and styrene had no effect on the kinetics of CYP119 Compound I decay. The substrate concentrations used in those studies were too small to give measurable kinetic effects.
45. Pan, Z. Z.; Zhang, R.; Newcomb, M. J. Inorg. Biochem. 2006, 100, 524-532.
46. Puchkaev, A. V.; Wakagi, T.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 2002, 124, 12682-12683.
47. Puchkaev, A. V.; Ortiz de Montellano, P. R. Arch. Biochem. Biophys. 2005, 434, 169-177.
48. Harischandra, D. N.; Zhang, R.; Newcomb, M. J. Am. Chem. Soc. 2005, 127, 13776-13777.
49. Pan, Z. Z.; Zhang, R.; Fung, L. W. M.; Newcomb, M. Inorg. Chem. 2007, 46, 1517-1519.
50. Koppenol, W. H. J. Am. Chem. Soc. 2007, 129, 9686-9690.
51. Rutter, R.; Hager, L. P.; Dhonau, H.; Hendrich, M.; Valentine, M.; Debrunner, P. Biochemistry 1984, 23, 6809-6816.
52. Kim, S. H.; Perera, R.; Hager, L. P.; Dawson, J. H.; Hoffman, B. M. J. Am. Chem. Soc. 2006, 128, 5598-5599.
53. Osborne, R. L.; Coggins, M. K.; Terner, J.; Dawson, J. H. J. Am. Chem. Soc. 2007, 129, 14838-14839.
54. Koo, L. S.; Immoos, C. E.; Cohen, M. S.; Farmer, P. J.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 2002, 124, 5684-5691.
55. Koo, L. S.; Tschirret-Guth, R. A.; Straub, W. E.; Moenne-Loccoz, P.; Loehr, T. M.; Ortiz de Montellano, P. R. J. Biol. Chem. 2000, 275, 14112-14123.
56. Nordblom, G. D.; White, R. E.; Coon, M. J. Arch. Biochem. Biophys. 1976, 175, 524-533.
57. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
58. Ren, Y.; Che, Y.; Ma, W.; Zhang, X.; Shen, T.; Zhao, J. New J. Chem. 2004, 28, 1464-1469.
59. Bartoli, J.-F.; Lambert, F.; Morgenstern-Badarau, I.; Battioni, P.; Mansuy, D. C. R. Chim. 2002, 5, 263-266.
60. Uppu, R. M.; Pryor, W. A. Anal. Biochem. 1996, 236, 242-249.
61. Yao, Z. J.; Wu, Y. L. J. Org. Chem. 1995, 60, 1170-1176.
62. Sawaki, Y.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6292-6296.
63. Groziak, M. P.; Chem, J. W.; Townsend, L. B. J. Org. Chem. 1986, 51, 1065-1069.