The monooxygenase, peroxidase, and peroxygenase properties of cytochrome P450

Archives of Biochemistry and Biophysics

Volumn 522, Issue 2, 2012, Pages 71-89

  Hrycay, Eugene G ^a   Bandiera, Stelvio M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Compound I; Cytochrome P450; Monooxygenase; Peroxidase; Peroxide shunt; Peroxygenase

Indexed keywords

AGROCYBE AEGERITA PEROXIDASE; ALDEHYDE; ALKENE; CHLORIDE PEROXIDASE; CYTOCHROME P450; FERRIC OXENOID COMPLEX; FERRIHYDROPEROXO COMPLEX; FERRIPEROXO COMPOUND; FERRYLOXY RADICAL COMPLEX; FUNGAL ENZYME; HEME PEROXIDASE; HORSERADISH PEROXIDASE; IODOSOBENZENE; IRON COMPLEX; NITRILE; OXYGEN; OXYGENASE; PERFERRYLOXO COMPLEX; PERIODATE; PEROXIDASE; PEROXIDE; PEROXYGENASE; PORPHYRIN; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARCHAEON; AROMATIZATION; BACTERIUM; CATALYSIS; CHEMICAL STRUCTURE; DECARBOXYLATION; ELECTRONICS; ENZYME ACTIVITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; EPOXIDATION; HUMAN; HYDROXYLATION; MAMMAL; NONHUMAN; OXIDATION; OXYGENATION; PRIORITY JOURNAL; QUANTUM MECHANICS; REVIEW; SULFOXIDATION;

ANIMALS; BIOCATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; MIXED FUNCTION OXYGENASES; PEROXIDASES; REACTIVE OXYGEN SPECIES;

ARCHAEA; BACTERIA (MICROORGANISMS); MAMMALIA;

EID: 84861333293     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2012.01.003     Document Type: Review

References (274)

1. D.R. Nelson, T. Kamataki, D.J. Waxman, F.P. Guengerich, R.W. Estabrook, R. Feyereisen, F.J. Gonzalez, M.J. Coon, I.C. Gunsalus, O. Gotoh, K. Okuda, and D.W. Nebert DNA Cell Biol. 12 1993 1 51
2. http://www.drnelson.uthsc.edu/cytochromeP450.html.
3. E.G. Hrycay, and S.M. Bandiera Cytochrome P450 enzymes S.C. Gad, Preclinical Development Handbook: ADME and Biopharmaceutical Properties 2008 John Wiley & Sons Inc. Hoboken, NJ 627 696
4. D.F.V. Lewis Cytochromes P450: Structure, Function and Mechanism 1996 Taylor and Francis London, UK
5. E.G. Hrycay, and S.M. Bandiera Curr. Drug Metab. 10 2009 1151 1183
6. P.R. Ortiz de Montellano, and J.J. De Voss Substrate oxidation by cytochrome P450 enzymes P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry third ed. 2005 Kluwer Academic/Plenum Publishers New York 183 245
7. G. Wächtershäuser Microbiol. Rev. 52 1988 452 484
8. R.H. Wickramasinghe, and C.A. Villee Nature 256 1975 509 511
9. B.K. Davis Prog. Biophys. Mol. Biol. 79 2002 77 133
10. A.R. Goeptar, H. Scheerens, and N.P.E. Vermeulen Crit. Rev. Toxicol. 25 1995 25 65
11. D.F.V. Lewis, and G. Sheridan The Scientific World 1 2001 151 167
12. F. Fischer, W. Zillig, K.O. Stetter, and G. Schreiber Nature 301 1983 511 513
13. D.F.V. Lewis Guide to Cytochromes P450: Structure and Function 2001 Taylor and Francis London, UK
14. F.P. Guengerich Chem. Res. Toxicol. 14 2001 611 650
15. E.G. Hrycay, and P.J. O'Brien Arch. Biochem. Biophys. 147 1971 14 27
16. E.G. Hrycay, and P.J. O'Brien Arch. Biochem. Biophys. 153 1972 480 494
17. E.G. Hrycay, P.J. O'Brien, J.E. Van Lier, and G. Kan Arch. Biochem. Biophys. 153 1972 495 501
18. E.G. Hrycay, and P.J. O'Brien Arch. Biochem. Biophys. 157 1973 7 22
19. E.G. Hrycay, and R.A. Prough Arch. Biochem. Biophys. 165 1974 331 339
20. E.G. Hrycay, J.Å. Gustafsson, M. Ingelman-Sundberg, and L. Ernster Biochem. Biophys. Res. Commun. 66 1975 209 216
21. E.G. Hrycay, J.Å. Gustafsson, M. Ingelman-Sundberg, and L. Ernster Eur. J. Biochem. 61 1976 43 52
22. J.Å. Gustafsson, E.G. Hrycay, and L. Ernster Arch. Biochem. Biophys. 174 1976 440 453
23. C.P. McKay, and H. Hartman Origins Life Evol. Biosph. 21 1991 157 163
24. V.D. Samuilov, Biochemistry (Moscow) 62 (1997) 451-454.
25. H. Joo, Z. Lin, and F.H. Arnold Nature 399 1999 670 673
26. L.S. Koo, R.A. Tschirret-Guth, W.E. Straub, P. Moënne-Loccoz, T.M. Loehr, and P.R. Ortiz de Montellano J. Biol. Chem. 275 2000 14112 14123
27. L.S. Koo, C.E. Immoos, M.S. Cohen, P.J. Farmer, and P.R. Ortiz de Montellano J. Am. Chem. Soc. 124 2002 5684 5691
28. D.G. Kellner, S.C. Hung, K.E. Weiss, and S.G. Sligar J. Biol. Chem. 277 2002 9641 9644
29. X. Sheng, J.H. Horner, and M. Newcomb J. Am. Chem. Soc. 130 2008 13310 13320
30. K.S. Rabe, K. Kiko, and C.M. Niemeyer ChemBioChem 9 2008 420 425
31. Y. Jiang, S. Sivaramakrishnan, T. Hayashi, S. Cohen, P. Moënne-Loccoz, S. Shaik, and P.R. Ortiz de Montellano Angew. Chem. 121 2009 7329 7331
32. D.F.V. Lewis J. Chem. Technol. Biotechnol. 77 2002 1095 1100
33. P.C. Cirino, and F.H. Arnold Angew. Chem. Int. Ed. 42 2003 3299 3301
34. S. Kumar Expert Opin. Drug Metab. Toxicol. 6 2010 115 131
35. S.L. Kelly, D.E. Kelly, C.J. Jackson, A.G.S. Warrilow, and D.C. Lamb The diversity and importance of microbial cytochromes P450 P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry third ed. 2005 Kluwer Academic/Plenum Publishers New York 585 617
36. C.R. Nishida, and P.R. Ortiz de Montellano Biochem. Biophys. Res. Commun. 338 2005 437 445
37. D.C. Lamb, L. Lei, A.G.S. Warrilow, G.I. Lepesheva, J.G.L. Mullins, M.R. Waterman, and S.L. Kelly J. Virol. 83 2009 8266 8269
38. A.W. Munro, H.M. Girvan, and K.J. McLean Biochim. Biophys. Acta 1770 2007 345 359
39. T. Omura, and R. Sato J. Biol. Chem. 239 1964 2370 2378
40. R.W. Estabrook Drug Metab. Dispos. 31 2003 1461 1473
41. 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
42. M. Sono, M.P. Roach, E.D. Coulter, and J.H. Dawson Chem. Rev. 96 1996 2841 2887
43. C.A. Hasemann, R.G. Kurumbail, S.S. Boddupalli, J.A. Peterson, and J. Deisenhofer Structure 2 1995 41 62
44. E.J. Mueller, P.J. Loida, and S.G. Sligar Twenty-five years of P450cam research: mechanistic insights into oxygenase catalysis P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry second ed. 1995 Plenum Press New York 83 124
45. A. Bast TIPS 7 1986 266 270
46. H. Kappus, and H. Sies Experientia 37 1981 1233 1241
47. H. Kappus Handb. Exp. Pharmacol. 105 1993 145 154
48. I.S. Young, and J.V. Woodside J. Clin. Pathol. 54 2001 176 186
49. D.F.V. Lewis, and J.M. Pratt Drug Metab. Rev. 30 1998 739 786
50. P.J. O'Brien Pharmacol. Ther. 2 1978 517 536
51. F.P. Guengerich, and W.W. Johnson Biochemistry 36 1997 14741 14750
52. F.P. Guengerich, and E.M. Isin Acta Chim. Slov. 55 2008 7 19
53. B. Meunier, and J. Bernadou Struct. Bonding 97 2000 1 35
54. S. Jin, T.M. Makris, T.A. Bryson, S.G. Sligar, and J.H. Dawson J. Am. Chem. Soc. 125 2003 3406 3407
55. J.T. Groves, G.A. McClusky, R.E. White, and M.J. Coon Biochem. Biophys. Res. Commun. 81 1978 154 160
56. P. George Biochem. J. 54 1953 267 276
57. H.S. Mason Adv. Enzymol. Relat. Subj. Biochem. 19 1957 79 233
58. G.A. Hamilton Adv. Enzymol. Relat. Areas Mol. Biol. 32 1969 55 96
59. S.G. Sligar, M.H. Gelb, and D.C. Heimbrook Xenobiotica 14 1984 63 86
60. P.M. Champion J. Am. Chem. Soc. 111 1989 3434 3436
61. Y. Urano, T. Higuchi, M. Hirobe, and T. Nagano J. Am. Chem. Soc. 119 1997 12008 12009
62. F.P. Guengerich, A.D.N. Vaz, G.N. Raner, S.J. Pernecky, and M.J. Coon Mol. Pharmacol. 51 1997 147 151
63. B. Meunier, S.P. de Visser, and S. Shaik Chem. Rev. 104 2004 3947 3980
64. A.D. Rahimtula, and P.J. O'Brien Biochem. Biophys. Res. Commun. 60 1974 440 447
65. M. Ingelman-Sundberg, and I. Johansson J. Biol. Chem. 259 1984 6447 6458
66. M. Ingelman-Sundberg, and G. Ekström Biochem. Biophys. Res. Commun. 106 1982 625 631
67. M. Ingelman-Sundberg, and A.L. Hagbjörk Xenobiotica 12 1982 673 686
68. A.I. Cederbaum, and L. Berl Arch. Biochem. Biophys. 216 1982 530 543
69. C. Ioannides, M. Delaforge, and D.V. Parke Food Cosmet. Toxicol. 19 1981 657 666
70. D.F.V. Lewis, C. Ioannides, and D.V. Parke Chem-Biol. Interact. 70 1989 263 280
71. H. Yasui, K. Deo, Y. Ogura, H. Yoshida, T. Shiraga, A. Kagayama, and H. Sakurai Drug Metab. Pharmacokinet. 17 2002 416 426
72. F.P. Guengerich, D.P. Ballou, and M.J. Coon Biochem. Biophys. Res Commun. 70 1976 951 956
73. S. Hayashi, H. Yasui, and H. Sakurai Drug Metab. Pharmacokinet. 20 2005 14 23
74. M. Hecker, W.J. Baader, P. Weber, and V. Ullrich Eur. J. Biochem. 169 1987 563 569
75. F.P. Guengerich Human cytochrome P450 enzymes P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry third ed. 2005 Kluwer Academic/Plenum Publishers New York 377 530
76. A.S. Kalgutkar, I. Gardner, R.S. Obach, C.L. Shaffer, E. Callegari, K.R. Henne, A.E. Mutlib, D.K. Dalvie, J.S. Lee, Y. Nakai, J.P. O'Donnell, J. Boer, and S.P. Harriman Curr. Drug Metab. 6 2005 161 225
77. A.K. Deo, and S.M. Bandiera Drug Metab. Dispos. 37 2009 1938 1947
78. X. Wu, A. Pramanik, M.W. Duffel, E.G. Hrycay, S.M. Bandiera, H.J. Lehmler, and I. Kania-Korwel Chem. Res. Toxicol. 24 2011 2249 2257
79. C.A. Erratico, S.C. Moffatt, and S.M. Bandiera Toxicol. Sci. 123 2011 37 47
80. J.H. Dawson Science 240 1988 433 439
81. C. Jung Biochim. Biophys. Acta. 1814 2011 46 57
82. P.R. Ortiz de Montellano Oxygen activation and transfer P.R. Ortiz de Montellano, Cytochrome P-450: Structure, Mechanism, and Biochemistry first ed. 1986 Plenum Press New York 217 271
83. P.F. Hollenberg FASEB J. 6 1992 686 694
84. J.T. Groves, and Y.Z. Han Models and mechanisms of cytochrome P450 action P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry second ed. 1995 Plenum Press New York 3 48
85. P.R. Ortiz de Montellano Oxygen activation and reactivity P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry second ed. 1995 Plenum Press New York 245 304
86. I.S. Isaac, and J.H. Dawson Essays Biochem. 34 1999 51 69
87. K.P. Vatsis, H.M. Peng, and M.J. Coon Arch. Biochem. Biophys. 434 2005 128 138
88. P.R. Ortiz de Montellano, and J.J. De Voss Nat. Prod. Rep. 19 2002 477 493
89. J.T. Groves Models and mechanisms of cytochrome P450 action P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry third ed. 2005 Kluwer Academic/Plenum Publishers New York 1 43
90. P.R. Ortiz de Montellano Chem. Rev. 110 2010 932 948
91. S. Shaik, S. Cohen, Y. Wang, H. Chen, D. Kumar, and W. Thiel Chem. Rev. 110 2010 949 1017
92. P.F. Hollenberg, T. Rand-Meir, and L.P. Hager J. Biol. Chem. 249 1974 5816 5825
93. V. Ullrich Topics Curr. Chem. 83 1979 67 104
94. P. Hlavica Eur. J. Biochem. 271 2004 4335 4360
95. T. Egawa, H. Shimada, and Y. Ishimura Biochem. Biophys. Res. Commun. 201 1994 1464 1469
96. T. Spolitak, J.H. Dawson, and D.P. Ballou J. Biol. Chem. 280 2005 20300 20309
97. V. Schünemann, C. Jung, J. Terner, A.X. Trautwein, and R. Weiss J. Inorg. Biochem. 91 2002 586 596
98. C. Jung, V. Schünemann, F. Lendzian, A.X. Trautwein, J. Contzen, M. Galander, L.H. Böttger, M. Richter, and A.L. Barra Biol. Chem. 386 2005 1043 1053
99. C. Jung, V. Schünemann, and F. Lendzian Biochem. Biophys. Res. Commun. 338 2005 355 364
100. M. Sivaraja, D.B. Goodin, M. Smith, and B.M. Hoffman Science 245 1989 738 740
101. R. Rutter, M. Valentine, M.P. Hendrich, L.P. Hager, and P.G. Debrunner Biochemistry 22 1983 4769 4774
102. X. Sheng, H. Zhang, S.C. Im, J.H. Horner, L. Waskell, P.F. Hollenberg, and M. Newcomb J. Am. Chem. Soc. 131 2009 2971 2976
103. T.M. Makris, K. von Koenig, I. Schlichting, and S.G. Sligar J. Inorg. Biochem. 100 2006 507 518
104. M.B. McCarthy, and R.E. White J. Biol. Chem. 258 1983 9153 9158
105. T.L. Poulos, B.C. Finzel, I.C. Gunsalus, G.C. Wagner, and J. Kraut J. Biol. Chem. 260 1985 16122 16130
106. M. Ator, S.K. David, and P.R. Ortiz de Montellano J. Biol. Chem. 264 1989 9250 9257
107. X. Yuan, Q. Wang, J.H. Horner, X. Sheng, and M. Newcomb Biochemistry 48 2009 9140 9146
108. P.R. Ortiz de Montellano, Y.S. Choe, G. DePillis, and C.E. Catalano J. Biol. Chem. 262 1987 11641 11646
109. X. Yi, M. Mroczko, K.M. Manoj, X. Wang, and L.P. Hager Proc. Natl. Acad. Sci. USA 96 1999 12412 12417
110. M.M. Palcic, R. Rutter, T. Araiso, L.P. Hager, and H.B. Dunford Spectrum of chloroperoxidase compound I Biochem. Biophys. Res. Commun. 94 1980 1123 1127
111. K. Auclair, P. Moënne-Loccoz, and P.R. Ortiz de Montellano J. Am. Chem. Soc. 123 2001 4877 4885
112. J. Rittle, and M.T. Green Science 330 2010 933 937
113. A.D. Rahimtula, P.J. O'Brien, E.G. Hrycay, J.A. Peterson, and R.W. Estabrook Biochem. Biophys. Res. Commun. 60 1974 695 702
114. R. Ullrich, and M. Hofrichter FEBS Lett. 579 2005 6247 6250
115. M. Hofrichter, and R. Ullrich Appl. Microbiol. Biotechnol. 71 2006 276 288
116. R. Ullrich, and M. Hofrichter Cell. Mol. Life Sci. 64 2007 271 293
117. H. Theorell, A. Ehrenberg, and B. Chance Arch. Biochem. Biophys. 37 1952 237 239
118. D. Dolphin, A. Forman, D.C. Borg, J. Fajer, and R.H. Felton Proc. Natl. Acad. Sci. USA 68 1971 614 618
119. H. Yamada, and I. Yamazaki Arch. Biochem. Biophys. 165 1974 728 738
120. B. Chance, L. Powers, Y. Ching, T. Poulos, G.R. Schonbaum, I. Yamazaki, and K.G. Paul Arch. Biochem. Biophys. 235 1984 596 611
121. S.L. Newmyer, J. Sun, T.M. Loehr, and P.R. Ortiz de Montellano Biochemistry 35 1996 12788 12795
122. T.L. Poulos Adv. Inorg. Biochem. 7 1988 1 36
123. D.R. Doerge, and M.D. Corbett Chem. Res. Toxicol. 4 1991 556 560
124. S. Colonna, N. Gaggero, A. Manfredi, L. Casella, M. Gullotti, G. Carrea, and P. Pasta Biochemistry 29 1990 10465 10468
125. T.D. Lindstrom, and S.D. Aust Arch. Biochem. Biophys. 233 1984 80 87
126. R.H. Weiss, J.L. Arnold, and R.W. Estabrook Arch. Biochem. Biophys. 252 1987 334 338
127. A.D.N. Vaz, and M.J. Coon Proc. Natl. Acad. Sci. USA 84 1987 1172 1176
128. G.D. Nordblom, R.E. White, and M.J. Coon Arch. Biochem. Biophys. 175 1976 524 533
129. B. Chance, H. Sies, and A. Boveris Physiol. Rev. 59 1979 527 605
130. A.D.N. Vaz, E.S. Roberts, and M.J. Coon Proc. Natl. Acad. Sci. USA 87 1990 5499 5503
131. L. Tan, E.G. Hrycay, and K. Matsumoto J. Steroid Biochem. 19 1983 1329 1338
132. J.A. Thompson, and N.P. Yumibe Drug Metab. Rev. 20 1989 365 378
133. Y.F. Ueng, T. Kuwabara, Y.J. Chun, and F.P. Guengerich Biochemistry 36 1997 370 381
134. C.J. Reed, and F. De Matteis Biochem. J. 261 1989 793 800
135. M.Y. Wang, and J.G. Liehr J. Biol. Chem. 269 1994 284 291
136. B. Testa Reductions catalyzed by cytochrome P450 and other oxidoreductases B. Testa, The Metabolism of Drugs and Other Xenobiotics: Biochemistry of Redox Reactions 1995 Academic Press London, UK 398 447
137. C.R. Otey, G. Bandara, J. Lalonde, K. Takahashi, and F.H. Arnold Biotechnol. Bioengin. 93 2006 494 499
138. D.P. Barr, M.V. Martin, F.P. Guengerich, and R.P. Mason Chem. Res. Toxicol. 9 1996 318 325
139. F.F. Kadlubar, K.C. Morton, and D.M. Ziegler Biochem. Biophys. Res. Commun. 54 1973 1255 1261
140. P.H. Bui, and O. Hankinson Mol. Pharmacol. 76 2009 1031 1043
141. P.H. Bui, E.L. Hsu, and O. Hankinson Mol. Pharmacol. 76 2009 1044 1052
142. P.J. O'Brien, and A. Rahimtula J. Agric. Food Chem. 23 1975 154 158
143. M.R. Anari, P.D. Josephy, T. Henry, and P.J. O'Brien Chem. Res. Toxicol. 10 1997 582 588
144. T.J. Smith, G.D. Stoner, and C.S. Yang Cancer Res. 55 1995 5566 5573
145. J.F. Muindi, and C.W. Young Cancer Res. 53 1993 1226 1229
146. B. Testa Reactions catalyzed by peroxidases B. Testa, The Metabolism of Drugs and Other Xenobiotics: Biochemistry of Redox Reactions 1995 Academic Press London, UK 346 388
147. M.D. Wand, and J.A. Thompson J. Biol. Chem. 261 1986 14049 14056
148. C. Larroque, R. Lange, L. Maurin, A. Bienvenue, and J.E. van Lier Arch. Biochem. Biophys. 282 1990 198 201
149. M.A. Correia, K. Yao, A.J. Allentoff, S.A. Wrighton, and J.A. Thompson Arch. Biochem. Biophys. 317 1995 471 478
150. B.W. Griffin, C. Marth, Y. Yasukochi, and B.S.S. Masters Arch. Biochem. Biophys. 205 1980 543 553
151. J. Capdevila, R.W. Estabrook, and R.A. Prough Arch. Biochem. Biophys. 200 1980 186 195
152. R. Renneberg, J. Capdevila, N. Chacos, R.W. Estabrook, and R.A. Prough Biochem. Pharmacol. 30 1981 843 848
153. R.C. Blake II, and M.J. Coon J. Biol. Chem. 256 1981 12127 12133
154. F. Lichtenberger, W. Nastainczyk, and V. Ullrich Biochem. Biophys. Res. Commun. 70 1976 939 946
155. J.Å. Gustafsson, and J. Bergman FEBS Lett. 70 1976 276 280
156. W.W. Ho, H. Li, C.R. Nishida, P.R. Ortiz de Montellano, and T.L. Poulos Biochemistry 47 2008 2071 2079
157. D.C. Heimbrook, R.I. Murray, K.D. Egeberg, S.G. Sligar, M.W. Nee, and T.C. Bruice J. Am. Chem. Soc. 106 1984 1514 1515
158. T.S. Dowers, D.A. Rock, D.A. Rock, and J.P. Jones J. Am. Chem. Soc. 126 2004 8868 8869
159. M.H. Gelb, D.C. Heimbrook, P. Mälkönen, and S.G. Sligar Biochemistry 21 1982 370 377
160. S.G. Sligar, K.A. Kennedy, and D.C. Pearson The chemical basis of mixed function oxidation T.E. King, H.S. Mason, M. Morrison, Oxidases and Related Redox Systems 1982 Permagon Press Oxford, UK 837 856
161. A. Berg, M. Ingelman-Sundberg, and J.Å. Gustafsson J. Biol. Chem. 254 1979 5264 5271
162. J.Å. Gustafsson, L. Rondahl, and J. Bergman Biochemistry 18 1979 865 870
163. K.B. Cho, Y. Moreau, D. Kumar, D.A. Rock, J.P. Jones, and S. Shaik Chem. Eur. J. 13 2007 4103 4115
164. Z. Pan, R. Zhang, and M. Newcomb J. Inorg. Biochem. 100 2006 524 532
165. T. Egawa, T. Ogura, R. Makino, Y. Ishimura, and T. Kitagawa J. Biol. Chem. 266 1991 10246 10248
166. M.T. Green J. Am. Chem. Soc. 121 1999 7939 7940
167. G.H. Loew, J. Collins, B. Luke, A. Waleh, and A. Padzianowski Enzyme 36 1986 54 78
168. S. Shaik, M. Filatov, D. Schröder, and H. Schwarz Chem. Eur. J. 4 1998 193 199
169. T. Ohno, N. Suzuki, T. Dokoh, Y. Urano, K. Kikuchi, M. Hirobe, T. Higuchi, and T. Nagano J. Inorg. Biochem. 82 2000 123 125
170. J.R. Lindsay-Smith, and P.R. Sleath J. Chem. Soc. Perkin Trans. 2 1983 621 628
171. Y. Watanabe, K. Yamaguchi, I. Morishima, K. Takehira, M. Shimizu, T. Hayakawa, and H. Orita Inorg. Chem. 30 1991 2581 2582
172. M. Newcomb, and R.E.P. Chandrasena Biochem. Biophys. Res. Commun. 338 2005 394 403
173. D.N. Harischandra, R. Zhang, and M. Newcomb J. Am. Chem. Soc. 127 2005 13776 13777
174. M. Newcomb, R. Zhang, R.E.P. Chandrasena, J.A. Halgrimson, J.H. Horner, T.M. Makris, and S.G. Sligar J. Am. Chem. Soc. 128 2006 4580 4581
175. Z. Pan, R.Q. Wang, X. Sheng, J.H. Horner, and M. Newcomb J. Am. Chem. Soc. 131 2009 2621 2628
176. R. Davydov, T.M. Makris, V. Kofman, D.E. Werst, S.C. Sligar, and B.M. Hoffman J. Am. Chem. Soc. 123 2001 1403 1415
177. G.H. Loew, and D.L. Harris Chem. Rev. 100 2000 407 419
178. R. Lange, G. Hui Bon Hoa, C. Larroque, and I.C. Gunsalus Kinetic and spectral investigation of cytochrome P-450 catalyzed oxygen activation I. Schuster, Cytochrome P-450: Biochemistry and Biophysics 1989 Taylor & Francis London, UK 272 275
179. I. Schlichting, J. Berendzen, K. Chu, A.M. Stock, S.A. Maves, D.E. Benson, R.M. Sweet, D. Ringe, G.A. Petsko, and S.G. Sligar Science 287 2000 1615 1622
180. S.A. Martinis, W.M. Atkins, P.S. Stayton, and S.G. Sligar J. Am. Chem. Soc. 111 1989 9252 9253
181. M. Imai, H. Shimada, Y. Watanabe, Y. Matsushima-Hibiya, R. Makino, H. Koga, T. Horiuchi, and Y. Ishimura Proc. Natl. Acad. Sci. USA 86 1989 7823 7827
182. R. Davydov, I.D.G. Macdonald, T.M. Makris, S.G. Sligar, and B.M. Hoffman J. Am. Chem. Soc. 121 1999 10654 10655
183. J. Rittle, J.M. Younker, and M.T. Green Inorg. Chem. 49 2010 3610 3617
184. I.G. Denisov, T.M. Makris, and S.G. Sligar J. Biol. Chem. 276 2001 11648 11652
185. T. Yonetani, and H. Schleyer J. Biol. Chem. 242 1967 1974 1979
186. G.C. Wagner, M.M. Palcic, and H.B. Dunford FEBS Lett. 156 1983 244 248
187. V. Schünemann, C. Jung, A.X. Trautwein, D. Mandon, and R. Weiss FEBS Lett. 479 2000 149 154
188. V. Schünemann, F. Lendzian, C. Jung, J. Contzen, A.L. Barra, S.G. Sligar, and A.X. Trautwein J. Biol. Chem. 279 2004 10919 10930
189. L.T. Burka, A. Thorsen, and F.P. Guengerich J. Am. Chem. Soc. 102 1980 7615 7616
190. J.T. Groves, T.E. Nemo, and R.S. Myers J. Am. Chem. Soc. 101 1979 1032 1033
191. R.C. Blake II, and M.J. Coon J. Biol. Chem. 264 1989 3694 3701
192. R. Zhang, R.E.P. Chandrasena, E. Martinez II, J.H. Horner, and M. Newcomb Org. Lett. 7 2005 1193 1195
193. S. Shaik, S. Cohen, S.P. de Visser, P.K. Sharma, D. Kumar, S. Kozuch, F. Ogliaro, D. Danovich, Eur. J. Inorg. Chem. (2004) 207-226.
194. S. Shaik, D. Kumar, S.P. de Visser, A. Altun, and W. Thiel Chem. Rev. 105 2005 2279 2328
195. S. Shaik, and S.P. De Visser Computational approaches to cytochrome P450 function P.R. Ortiz de Montellano, Cytochrome P450: Structure, Mechanism, and Biochemistry third ed. 2005 Kluwer Academic/Plenum Publishers New York 45 85
196. H. Chen, J. Song, W. Lai, W. Wu, and S. Shaik J. Chem. Theory Comput. 6 2010 940 953
197. S. Cohen, D. Kumar, and S. Shaik J. Am. Chem. Soc. 128 2006 2649 2653
198. S. Sivaramakrishnan, H. Ouellet, Y. Jiang, T. Hayashi, P. Moënne-Loccoz, P.R. Ortiz de Montellano, Expression, Characterization and Functional Properties of a Selenocysteine Substituted Cytochrome P450 Enzyme, in: 16th North American Regional ISSX Meeting, October 18-22, 2009, Baltimore, Abstract No. 116.
199. S.G. Sligar, B.S. Shastry, and I.C. Gunsalus Oxygen reactions of the P450 heme protein V. Ullrich, I. Roots, A. Hildebrandt, R.W. Estabrook, A.H. Conney, Microsomes and Drug Oxidations 1977 Permagon Press Oxford 202 209
200. B. Munge, C. Estavillo, J.B. Schenkman, and J.F. Rusling ChemBioChem 4 2003 82 89
201. Q.S. Li, J. Ogawa, and S. Shimizu Biochem. Biophys. Res. Commun. 280 2001 1258 1261
202. K.K. Khan, Y.A. He, Y.Q. He, and J.R. Halpert Chem. Res. Toxicol. 15 2002 843 853
203. I. Matsunaga, A. Ueda, T. Sumimoto, K. Ichihara, M. Ayata, and H. Ogura Arch. Biochem. Biophys. 394 2001 45 53
204. O. Shoji, T. Fujishiro, H. Nakajima, M. Kim, S. Nagano, and Y. Shiro Angew. Chem. Int. Ed. 46 2007 3656 3659
205. M. Girhard, S. Schuster, M. Dietrich, P. Dürre, and V.B. Urlacher Biochem. Biophys. Res. Commun. 362 2007 114 119
206. I. Matsunaga, M. Yamada, E. Kusunose, T. Miki, and K. Ichihara J. Biochem. 124 1998 105 110
207. H. Ogura, C.R. Nishida, U.R. Hoch, R. Perera, J.H. Dawson, and P.R. Ortiz de Montellano Biochemistry 43 2004 14712 14721
208. S. Kumar, H. Liu, and J.R. Halpert Drug Metab. Dispos. 34 2006 1958 1965
209. P. Hlavica, and U. Künzel-Mulas Biochim. Biophys. Acta 1158 1993 83 90
210. S. Kumar, C.S. Chen, D.J. Waxman, and J.R. Halpert J. Biol. Chem. 280 2005 19569 19575
211. P.H.J. Keizers, L.H.M. Schraven, C. de Graaf, M. Hidestrand, M. Ingelman-Sundberg, B.R. van Dijk, N.P.E. Vermeulen, and J.N.M. Commandeur Biochem. Biophys. Res. Commun. 338 2005 1065 1074
212. A.D. Rahimtula, and P.J. O'Brien Eur. J. Biochem. 77 1977 201 208
213. I. Kania-Korwel, E.G. Hrycay, S.M. Bandiera, and H.J. Lehmler Chem. Res. Toxicol. 21 2008 1295 1303
214. J. Segura-Aguilar Biochem. Mol. Med. 58 1996 122 129
215. G.P. McCallum, A.C. Weedon, P. Krug, and J.R. Bend J. Pharmacol. Exp. Ther. 278 1996 1188 1194
216. A.I. Cederbaum Arch. Biochem. Biophys. 227 1983 329 338
217. G.T. Miwa, W. Levin, P.E. Thomas, and A.Y.H. Lu Arch. Biochem. Biophys. 187 1978 464 475
218. Å. Ellin, and S. Orrenius FEBS Lett. 50 1975 378 381
219. H. Danielsson, and K. Wikvall FEBS Lett. 66 1976 299 302
220. D. Roy, A. Bernhardt, H.W. Strobel, and J.G. Liehr Arch. Biophys. Biophys. 296 1992 450 456
221. Q. Bui, and J. Weisz Pharmacology 36 1988 356 364
222. D.C. Spink, B.C. Spink, X. Zhuo, M.M. Hussain, J.F. Gierthy, and X. Ding J. Steroid Biochem. Mol. Biol. 74 2000 11 18
223. V. Ullrich Arch. Biochem. Biophys. 409 2003 45 51
224. M.R. Anari, S. Khan, and P.J. O'Brien Chem. Res. Toxicol. 9 1996 924 931
225. R.A. Stearns, and P.R. Ortiz de Montellano J. Am. Chem. Soc. 107 1985 4081 4082
226. M. Akhtar, M.R. Calder, D.L. Corina, and J.N. Wright Biochem. J. 201 1982 569 580
227. M. Akhtar, V.C.O. Njar, and J.N. Wright J. Steroid Biochem. Mol. Biol. 44 1993 375 387
228. M. Akhtar, D. Corina, S. Miller, A.Z. Shyadehi, and J.N. Wright Biochemistry 33 1994 4410 4418
229. J.C. Hackett, R.W. Brueggemeier, and C.M. Hadad J. Am. Chem. Soc. 127 2005 5224 5237
230. A.D.N. Vaz, E.S. Roberts, and M.J. Coon J. Am. Chem. Soc. 113 1991 5886 5887
231. E.S. Roberts, A.D.N. Vaz, and M.J. Coon Proc. Natl. Acad. Sci. USA 88 1991 8963 8966
232. A.D.N. Vaz Curr. Drug Metab. 2 2001 1 16
233. M. Newcomb, P.F. Hollenberg, and M.J. Coon Arch. Biochem. Biophys. 409 2003 72 79
234. A.D.N. Vaz, S.J. Pernecky, G.M. Raner, and M.J. Coon Proc. Natl. Acad. Sci. USA 93 1996 4644 4648
235. Z. Zhang, Y. Li, R.A. Stearns, P.R. Ortiz de Montellano, T.A. Baillie, and W. Tang Biochemistry 41 2002 2712 2718
236. A.D.N. Vaz, D.F. McGinnity, and M.J. Coon Proc. Natl. Acad. Sci. USA 95 1998 3555 3560
237. M. Newcomb, M.H. Le Tadic, D.A. Putt, and P.F. Hollenberg J. Am. Chem. Soc. 117 1995 3312 3313
238. M. Newcomb, M.H. Le Tadic-Biadatti, D.L. Chestney, E.S. Roberts, and P.F. Hollenberg J. Am. Chem. Soc. 117 1995 12085 12091
239. P.H. Toy, M. Newcomb, M.J. Coon, and A.D.N. Vaz J. Am. Chem. Soc. 120 1998 9718 9719
240. M. Newcomb, and P.H. Toy Acc. Chem. Res. 33 2000 449 455
241. M. Newcomb, R. Shen, S.Y. Choi, P.H. Toy, P.F. Hollenberg, A.D.N. Vaz, and M.J. Coon J. Am. Chem. Soc. 122 2000 2677 2686
242. M. Newcomb, D. Aebisher, R. Shen, R.E.P. Chandrasena, P.F. Hollenberg, and M.J. Coon J. Am. Chem. Soc. 125 2003 6064 6065
243. K.P. Vatsis, and M.J. Coon Arch. Biochem. Biophys. 397 2002 119 129
244. T.J. Volz, D.A. Rock, and J.P. Jones J. Am. Chem. Soc. 124 2002 9724 9725
245. Y. Watanabe J. Biol. Inorg. Chem. 6 2001 846 856
246. F. Ogliaro, S.P. de Visser, S. Cohen, P.K. Sharma, and S. Shaik J. Am. Chem. Soc. 124 2002 2806 2817
247. S. Shaik, S.P. de Visser, and D. Kumar J. Biol. Inorg. Chem. 9 2004 661 668
248. D.F. McGinnity, A.D.N. Vaz, M.J. Coon, FASEB J. 11 (1997) A807 (Abstr.).
249. T. Ohe, T. Mashino, and M. Hirobe Drug Metab. Dispos. 25 1997 116 122
250. S.B. Karki, J.P. Dinnocenzo, J.P. Jones, and K.R. Korzekwa J. Am. Chem. Soc. 117 1995 3657 3664
251. C.L. Shaffer, S. Harriman, Y.M. Koen, and R.P. Hanzlik J. Am. Chem. Soc. 124 2002 8268 8274
252. P.K. Sharma, S.P. de Visser, and S. Shaik J. Am. Chem. Soc. 125 2003 8698 8699
253. S.P. de Visser, F. Ogliaro, P.K. Sharma, and S. Shaik J. Am. Chem. Soc. 124 2002 11809 11826
254. Y. Goto, T. Matsui, S. Ozaki, Y. Watanabe, and S. Fukuzumi J. Am. Chem. Soc. 121 1999 9497 9502
255. R.E. White, J.P. Miller, L.V. Favreau, and A. Bhattacharyaa J. Am. Chem. Soc. 108 1986 6024 6031
256. F. Ogliaro, N. Harris, S. Cohen, M. Filatov, S. de Visser, and S. Shaik J. Am. Chem. Soc. 122 2000 8977 8989
257. L.M. Hjelmeland, L. Aronow, and J.R. Trudell Biochem. Biophys. Res. Commun. 76 1977 541 549
258. A.B. Foster Adv. Drug Res. 14 1985 2 40
259. S. Kadkhodayan, E.D. Coulter, D.M. Maryniak, T.A. Bryson, and J.H. Dawson J. Biol. Chem. 270 1995 28042 28048
260. K. Tanaka, N. Kurihara, and M. Nakajima Pestic. Biochem. Physiol. 10 1979 79 95
261. J.T. Groves, and D.V. Subramanian J. Am. Chem. Soc. 106 1984 2177 2181
262. E.H. Oliw, I.D. Brodowsky, L. Hörnsten, and M. Hamberg Arch. Biochem. Biophys. 300 1993 434 439
263. P.R. Ortiz de Montellano, and R.A. Stearns J. Am. Chem. Soc. 109 1987 3415 3420
264. V.W. Bowry, and K.U. Ingold J. Am. Chem. Soc. 113 1991 5699 5707
265. J.K. Atkinson, and K.U. Ingold Biochemistry 32 1993 9209 9214
266. R.E.P. Chandrasena, K.P. Vatsis, M.J. Coon, P.F. Hollenberg, and M. Newcomb J. Am. Chem. Soc. 126 2004 115 126
267. D. Kumar, S.P. de Visser, and S. Shaik J. Am. Chem. Soc. 125 2003 13024 13025
268. J.M. Pratt, T.I. Ridd, and L.J. King J. Chem. Soc. Chem. Commun. 22 1995 2297 2298
269. R. Renneberg, F. Scheller, K. Ruckpaul, J. Pirrwitz, and P. Mohr FEBS Lett. 96 1978 349 353
270. D.R. Koop, and P.F. Hollenberg J. Biol. Chem. 255 1980 9685 9692
271. R.W. Estabrook, C. Martin-Wixtrom, Y. Saeki, R. Renneberg, A. Hildebrandt, and J. Werringloer Xenobiotica 14 1984 87 104
272. D.W. Potter, and J.A. Hinson J. Biol. Chem. 262 1987 966 973
273. S.V. Otton, E.M. Gillam, M.S. Lennard, G.T. Tucker, and H.F. Woods Br. J. Clin. Pharmacol. 30 1990 751 760
274. D.H. Kim, T. Ahn, H.C. Jung, J.G. Pan, and C.H. Yun Drug Metab. Dispos. 37 2009 932 936