Kinetics of oxidation of benzphetamine by compounds I of cytochrome P450 2B4 and its mutants

Journal of the American Chemical Society

Volumn 131, Issue 8, 2009, Pages 2971-2976

  Sheng, Xin ^a   Zhang, Haoming ^b   Im, Sang Choul ^b   Horner, John H ^a   Waskell, Lucy ^b   Hollenberg, Paul F ^b   Newcomb, Martin ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING CONSTANT; COMPOUND I; CYTOCHROME P450; CYTOCHROMES P450; FIRST-ORDER; HIGH YIELD; INTRINSIC REACTIVITY; KINETIC STUDY; KINETICS OF OXIDATION; LASER FLASH PHOTOLYSIS; ORDER OF MAGNITUDE; OVERALL RATE; OXIDATION RATES; OXIDATION REACTIONS; PEROXYNITRITE; RADICAL CATIONS; SATURATION KINETICS; SUBSTRATE BINDING; TEST REACTIONS;

CATALYSTS; ENZYMES; EQUILIBRIUM CONSTANTS; MAMMALS; MASS SPECTROMETRY; OXIDATION; PHOTOLYSIS; PORPHYRINS;

RATE CONSTANTS;

BENZPHETAMINE; CYTOCHROME P450; CYTOCHROME P450 2B4; PEROXYNITRITE; ARCHAEAL PROTEIN; CYP119 PROTEIN, SULFOLOBUS SOLFATARICUS; CYTOCHROME P 450 CYP2B4 (RABBIT); CYTOCHROME P-450 CYP2B4 (RABBIT); UNSPECIFIC MONOOXYGENASE;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; COMPARATIVE STUDY; ENZYME MECHANISM; EQUILIBRIUM CONSTANT; KINETICS; LASER; MAMMAL; MASS SPECTROMETRY; MUTANT; NITRATION; NONHUMAN; PHOTOLYSIS; PHOTOOXIDATION; SPECIES; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; ULTRAVIOLET SPECTROPHOTOMETRY;

ARCHAEAL PROTEINS; ARYL HYDROCARBON HYDROXYLASES; BENZPHETAMINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; KINETICS; MODELS, MOLECULAR; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; PHOTOLYSIS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 67749093242     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808982g     Document Type: Article

References (48)

1. Ortiz de Montellano, P. R. Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd 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 Metabol. Rev. 2004, 36, 511-529.
6. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
7. Egawa, T.; Shimada, H.; Ishimura, Y. Biochem. Biophys. Res. Commun. 1994, 201, 1464-1469.
8. Spolitak, T.; Dawson, J. H.; Ballou, D. P. J. Biol. Chem. 2005, 280, 20300-20309.
9. Schünemann, V.; Jung, C.; Terner, J.; Trautwein, A. X.; Weiss, R. J. Inorg. Biochem. 2002, 91, 586-596.
10. Jung, C.; Schünemann, V.; Lendzian, F.; Trautwein, A. X.; Contzen, J.; Galander, M.; Böttger, L. H.; Richter, M.; Barra, A. L. Biol. Chem. 2005, 386, 1043-1053.
11. Davydov, R.; Makris, T. M.; Kofman, V.; Werst, D. E.; Sligar, S. G.; Hoffman, B. M. J. Am. Chem. Soc 2001, 123, 1403-1415.
12. Zhang, R.; Chandrasena, R. E. P.; Martinez II, E.; Horner, J. H.; Newcomb, M. Org. Lett. 2005, 7, 1193-1195.
13. 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.
14. Sheng, X.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2008, 130, 13310-13320.
15. Lu, A. Y. H.; Coon, M. J. J. Biol. Chem. 1968, 243, 1331-1332.
16. 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.
17. Sheng, X.; Zhang, H.; Hollenberg, P. F.; Newcomb, M. Biochemistry 2009, 48, 0000-0000.
18. Mehl, M.; Daiber, A.; Herold, S.; Shoun, H.; Ullrich, V. Nitric Oxide 1999, 3, 142-152.
19. Daiber, A.; Herold, S.; Schöneich, C.; Namgaladze, D.; Peterson, J. A.; Ullrich, V. Eur. J. Biochem. 2000, 267, 6729-6739.
20. Gebicka, L.; Didik, J. J. Inorg. Biochem. 2007, 101, 159-164.
21. Lin, H. L.; Myshkin, E.; Waskell, L.; Hollenberg, P. F. Chem. Res. Toxicol. 2007, 20, 1612-1622.
22. Toy, P. H.; Newcomb, M.; Coon, M. J.; Vaz, A. D. N. J. Am. Chem. Soc. 1998, 120, 9718-9719.
23. Palcic, M. M.; Rutter, R.; Araiso, T.; Hager, L. P.; Dunford, H. B. Biochem. Biophys. Res. Commun. 1980, 94, 1123-1127.
24. Egawa, T.; Proshlyakov, D. A.; Miki, H.; Makino, R.; Ogura, T.; Kitagawa, T.; Ishimura, Y. J. Biol. Inorg. Chem. 2001, 6, 46-54.
25. Zhang, H. M.; Im, S. C.; Waskell, L. J. Biol. Chem. 2007, 282, 29766-29776.
26. Nagano, S.; Poulos, T. L. J. Biol. Chem. 2005, 280, 31659-31663.
27. Roberts, E. S.; Pernecky, S. J.; Alworth, W. L.; Hollenberg, P. F. Arch. Biochem. Biophys. 1996, 331, 170-176.
28. Vaz, A. D. N.; McGinnity, D. F.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3555-3560.
29. Newcomb, M.; Aebisher, D.; Shen, R. N.; Chandrasena, R. E. P.; Hollenberg, P. F.; Coon, M. J. J. Am. Chem. Soc. 2003, 125, 6064-6065.
30. Newcomb, M.; Shen, R.; Choi, S. Y.; Toy, P. H.; Hollenberg, P. F.; Vaz, A. D. N.; Coon, M. J. J. Am. Chem. Soc. 2000, 122, 2677-2686.
31. Imai, M.; Shimada, H.; Watanabe, Y.; Matsushimahibiya, Y.; Makino, R.; Koga, H.; Horiuchi, T.; Ishimura, Y. Proc Natl. Acad. Sci. U.S.A. 1989, 86, 7823-7827.
32. Martinis, S. A.; Atkins, W. M.; Stayton, P. S.; Sligar. S. G. J. Am. Chem. Soc. 1989, 111, 9252-9253.
33. Jin, S. X.; Makris, T. M.; Bryson, T. A.; Sligar, S. G.; Dawson, J. H. J. Am. Chem. Soc. 2003, 125, 3406-3407.
34. Yeom, H.; Sligar, S. G.; Li, H. Y.; Poulos, T. L.; Fulco, A. J. Biochemistry 1995, 34, 14733-14740.
35. Newcomb, M.; Hollenberg, P. F.; Coon, M. J. Arch. Biochem. Biophys. 2003, 409, 72-79.
36. Chandrasena, R. E. P.; Vatsis, K. P.; Coon, M. J.; Hollenberg, P. F.; Newcomb, M. J. Am. Chem. Soc. 2004, 126, 115-126.
37. Vatsis, K. P.; Peng, H. M.; Coon, M. J. Inorg. Biochem. 2002, 91, 542-553.
38. Ost, T. W. B.; Miles, C. S.; Munro, A. W.; Murdoch, J.; Reid, G. A.; Chapman, S. K. Biochemistry 2001, 40, 13421-13429.
39. Pan, Z.; Zhang, R.; Newcomb, M. J. Inorg. Biochem. 2006, 100, 524-532.
40. Harischandra, D. N.; Zhang, R.; Newcomb, M. J. Am. Chem. Soc. 2005, 127, 13776-13777.
41. Pan, Z.; Zhang, R.; Fung, L. W. M.; Newcomb, M. Inorg. Chem. 2007, 46, 1517-1519.
42. Hanna, I. H.; Teiber, J. F.; Kokones, K. L.; Hollenberg, P. F. Arch. Biochem. Biophys. 1998, 350, 324-332.
43. Saribas, A. S.; Gruenke, L.; Waskell, L. Protein Expression Purif. 2001, 21, 303-309.
44. McLean, M. A.; Maves, S. A.; Weiss, K. E.; Krepich, S.; Sligar, S. G. Biochem. Biophys. Res. Commun. 1998, 252, 166-172.
45. Maves, S. A.; Sligar, S. G. Protein Sci. 2001, 10, 161-168.
46. Uppu, R. M.; Pryor, W. A. Anal. Biochem. 1996, 236, 242-249.
47. Fu, H.; Newcomb, M.; Wong, C.-H. J. Am. Chem. Soc 1991, 113, 5878-5880.
48. Atkinson, J. K.; Hollenberg, P. F.; Ingold, K. U.; Johnson, C. C.; Le Tadic, M.-H.; Newcomb, M.; Putt, D. A. Biochemistry 1994, 33, 10630-10637.