Substrate binding to cytochromes P450

Analytical and Bioanalytical Chemistry

Volumn 392, Issue 6, 2008, Pages 1019-1030

  Isin, Emre M ^a   Guengerich, F Peter ^b  

^a ASTRAZENECA R AND D   (Sweden)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Cooperativity; Cytochrome P450; Drug development; Ligands; Substrate binding

Indexed keywords

BIOCHEMISTRY; CHEMICAL OXYGEN DEMAND; OXIDATION;

BINDING STUDIES; CATALYTIC CYCLES; COOPERATIVITY; CYTOCHROME P450; CYTOCHROMES P450; DRUG DEVELOPMENT; DRUG MOLECULES; ENDOGENOUS SUBSTRATES; EXTENDING; H BONDS; MECHANISM OF OXIDATIONS; SUBSTRATE BINDING; SUBSTRATE BINDINGS; SUBSTRATE OXIDATIONS; SUBSTRATE PROPERTIES;

SUBSTRATES;

CYTOCHROME P450; LIGAND;

ANIMAL; BINDING SITE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION; REVIEW;

ANIMALS; BINDING SITES; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; LIGANDS; OXIDATION-REDUCTION; SUBSTRATE SPECIFICITY;

EID: 54949132112     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-008-2244-0     Document Type: Review

References (196)

1. FP Guengerich 1994 Toxicol Lett 70 133 138
2. Ortiz de Montellano PR (2005) Cytochrome P450: structure, mechanism, and biochemistry, 3rd edn. Kluwer/Plenum, New York
3. IG Denisov TM Makris SG Sligar I Schlichting 2005 Chem Rev 105 2253 2277
4. FP Guengerich 2008 Chem Res Toxicol 21 70 83
5. DFV Lewis Y Ito PS Goldfarb 2006 Drug Dev Res 66 19 24
6. DR Nelson L Koymans T Kamataki JJ Stegeman R Feyereisen DJ Waxman MR Waterman O Gotoh MJ Coon RW Estabrook IC Gunsalus DW Nebert 1996 Pharmacogenetics 6 1 42
7. M Katagiri BN Ganguli IC Gunsalus 1968 J Biol Chem 243 3543 3546
8. SG Sligar IC Gunsalus 1976 Proc Natl Acad Sci USA 73 1078 1082
9. CA Tyson JD Lipscomb IC Gunsalus 1972 J Biol Chem 247 5777 5784
10. TL Poulos R Raag 1992 FASEB J 6 674 679
11. FP Guengerich TL Macdonald 1984 Acc Chem Res 17 9 16
12. FP Guengerich 2001 Chem Res Toxicol 14 611 650
13. Guengerich FP (2005) In: Ortiz de Montellano PR (ed) Cytochrome P450: structure, mechanism, and biochemistry, 3rd edn. Kluwer/Plenum, New York, pp 377-530
14. K Stark FP Guengerich 2007 Drug Metab Rev 39 627 637
15. JA Williams R Hyland BC Jones DA Smith S Hurst TC Goosen V Peterkin JR Koup SE Ball 2004 Drug Metab Dispos 32 1201 1208
16. LC Wienkers TG Heath 2005 Nat Rev Drug Discov 4 825 833
17. DW Nebert DW Russell 2002 Lancet 360 1155 1162
18. EM Isin FP Guengerich 2006 Biochim Biophys Acta 1770 314 329
19. FP Guengerich EM Isin 2008 Acta Chem Sloven 55 7 19
20. C-H Yun K-H Kim MW Calcutt FP Guengerich 2005 J Biol Chem 280 12279 12291
21. EM Isin FP Guengerich 2006 J Biol Chem 281 9127 9136
22. JB Schenkman H Remmer RW Estabrook 1967 Mol Pharmacol 3 113 123
23. M Sharrock E Muenck PG Debrunner V Marshall JD Lipscomb IC Gunsalus 1973 Biochemistry 12 258 265
24. SN Daff SK Chapman KL Turner RA Holt S Govindaraj TL Poulos AW Munro 1997 Biochemistry 36 13816 13823
25. Aguey-Zinsou K-F, Bernhardt PV, De Voss JJ, Slessor KE (2003) Chem Commun 418-419
26. FP Guengerich 1983 Biochemistry 22 2811 2820
27. WL Backes SG Sligar JB Schenkman 1982 Biochemistry 21 1324 1330
28. YY Huang T Hara S Sligar MJ Coon T Kimura 1986 Biochemistry 25 1390 1394
29. WL Backes CS Eyer 1989 J Biol Chem 264 6252 6259
30. H Yamazaki WW Johnson Y-F Ueng T Shimada FP Guengerich 1996 J Biol Chem 271 27438 27444
31. FP Guengerich WW Johnson 1997 Biochemistry 36 14741 14750
32. Fersht A (1999) Structure and mechanism in protein science. Freeman, New York
33. A Das YV Grinkova SG Sligar 2007 J Am Chem Soc 129 13778 13779
34. NA Hosea GP Miller FP Guengerich 2000 Biochemistry 39 5929 5939
35. EM Isin FP Guengerich 2007 J Biol Chem 282 6863 6874
36. BW Griffin JA Peterson 1972 Biochemistry 11 4740 4746
37. Y-J Chun T Shimada R Sanchez-Ponz MV Martin L Lei B Zhao SL Kelly MR Waterman DC Lamb FP Guengerich 2007 J Biol Chem 282 17486 17500
38. AG Roberts WM Atkins 2007 Arch Biochem Biophys 463 89 101
39. IG Denisov BJ Baas YV Grinkova SG Sligar 2007 J Biol Chem 282 7066 7076
40. M-Y Yoon AP Campbell WM Atkins 2004 Drug Metab Rev 36 219 230
41. CD Sohl EM Isin RL Eoff GA Marsch DF Stec FP Guengerich 2008 J Biol Chem 283 7293 7308
42. H Fernando JR Halpert DR Davydov 2006 Biochemistry 45 4199 4209
43. J Cupp-Vickery R Anderson Z Hatziris 2000 Proc Natl Acad Sci USA 97 3050 3055
44. B Zhao DC Lamb L Lei SL Kelly H Yuan DL Hachey MR Waterman 2007 Biochemistry 46 8725 8733
45. B Zhao FP Guengerich A Bellamine DC Lamb M Izumikawa N Funa L Lei LM Podust M Sundamoorthy LM Reddy SL Kelly D Stec M Voehler JR Falck BS Moore T Shimada MR Waterman 2005 J Biol Chem 280 11599 11607
46. M Ekroos T Sjögren 2006 Proc Nat Acad Sci USA 103 13682 13687
47. EF Johnson CD Stout 2005 Biochem Biophys Res Commun 338 331 336
48. Poulos TL, Johnson EF (2005) In: Ortiz de Montellano PR (ed) Cytochrome P450: structure mechanism, and biochemistry, 3rd edn. Kluwer/Plenum, New York, pp 87-114
49. M Otyepka J Skopalik E Anzenbacherova P Anzenbacher 2007 Biochim Biophys Acta 1770 376 389
50. KC Leibman AG Hildebrandt RW Estabrook 1969 Biochem Biophys Res Commun 36 789 794
51. F Mitani S Horie 1969 J Biochem 66 139 149
52. CR Jefcoate 1978 Methods Enzymol 52 258 279
53. DF Lewis 2003 Arch Biochem Biophys 409 32 44
54. WM Atkins 2006 Expert Opin Drug Metab Toxicol 2 573 579
55. Y-F Ueng T Kuwabara Y-J Chun FP Guengerich 1997 Biochemistry 36 370 381
56. TS Tracy 2006 Drugs R D 7 349 363
57. FP Guengerich 1999 Annu Rev Pharmacol Toxicol 39 1 17
58. GR Harlow JR Halpert 1998 Proc Natl Acad Sci USA 95 6636 6641
59. AG Roberts AP Campbell WM Atkins 2005 Biochemistry 44 1353 1366
60. MD Cameron B Wen AG Roberts WM Atkins AP Campbell SD Nelson 2007 Chem Res Toxicol 20 1434 1441
61. DR Davydov H Fernando JR Halpert 2006 Biophys Chem 123 95 101
62. P Job 1928 Ann Chim Appl 9 113 203
63. A Facchiano R Ragone 2003 Anal Biochem 313 170 172
64. BJ Baas IG Denisov SG Sligar 2004 Arch Biochem Biophys 430 218 228
65. A Nath YV Grinkova SG Sligar WM Atkins 2007 J Biol Chem 282 28309 28320
66. K Venkatakrishnan LL Von Moltke DJ Greenblatt 1998 J Pharm Sci 87 1502 1507
67. GP Miller FP Guengerich 2001 Biochemistry 40 7262 7272
68. EM Isin CD Sohl RL Eoff FP Guengerich 2008 Arch Biochem Biophys 473 69 75
69. BD Burleigh Jr GP Foust CH Williams Jr 1969 Anal Biochem 27 536 544
70. GP Foust BD Burleigh Jr SG Mayhew CH Williams Jr V Massey 1969 Anal Biochem 27 530 535
71. FP Guengerich JA Krauser WW Johnson 2004 Biochemistry 43 10775 10788
72. Walsh C (1979) Enzymatic reaction mechanisms. Freeman, San Francisco
73. H Yao CR [tmp] McCullough AD Costache PK Pullela DS Sem 2007 Proteins Struct Funct Bioinf 69 125 138
74. Lakowicz JR (1999) Principles of fluorescence spectroscopy. Kluwer/Plenum, New York
75. P Sandhu Z Guo T Baba MV Martin RH Tukey FP Guengerich 1994 Arch Biochem Biophys 309 168 177
76. G Weber FJW Teale 1959 Discuss Faraday Soc 27 134 141
77. T Förster 1969 Angew Chem Int Ed Engl 8 333 343
78. SS Lehrer 1997 Methods Enzymol 278 286 295
79. MJ Dabrowski ML Schrag LC Wienkers WM Atkins 2002 J Am Chem Soc 124 11866 11867
80. DR Davydov S Kumar JR Halpert 2002 Biochem Biophys Res Commun 294 806 812
81. PA Williams J Cosme DM Vinkovic A Ward HC Angove PJ Day C Vonrhein IJ Tickle H Jhoti 2004 Science 305 683 686
82. He Y-A, Gajiwala KS, Wu M, Parge H, Burke B, Lee CA, Wester MR (2006) Paper presented at the 16th international symposium on microsomes and drug oxidations (MDO 2006), Budapest, Hungary
83. S Prasad S Mazumdar S Mitra 2000 FEBS Lett 477 157 160
84. S Prasad S Mitra 2002 Biochemistry 41 14499 14508
85. A Stortelder PHJ Keizers C Oostenbrink C De Graaf P De Kruijf NPE Vermeulen C Gooijer JNM Commandeur G Van der Zwan 2006 Biochem J 393 635 643
86. JN Lampe WM Atkins 2006 Biochemistry 45 12204-1221
87. JN Lampe C Fernandez A Nath WM Atkins 2008 Biochemistry 47 509 516
88. L Stryer 1965 J Mol Biol 13 482 495
89. A Chougnet C Stoessel W-D Woggon 2003 Bioorg Med Chem Lett 13 3643 3645
90. A Chougnet Y Grinkova D Ricard S Sligar W-D Woggon 2007 ChemMedChem 2 717 724
91. DL Sackett J Wolff 1987 Anal Biochem 167 228 234
92. DR Davydov AE Botchkareva NE Davydova JR Halpert 2005 Biophys J 89 418 432
93. TN Tsalkova NY Davydova JR Halpert DR Davydov 2007 Biochemistry 46 106 119
94. SB Shuker PJ Hajduk RP Meadows SW Fesik 1996 Science 274 1531 1534
95. A Medek ET Olejniczak RP Meadows SW Fesik 2000 J Biomol NMR 18 229 238
96. TC Pochapsky M Kostic N Jain R Pejchal 2001 Biochemistry 40 5602 5614
97. J Marley M Lu C Bracken 2001 J Biomol NMR 20 71 75
98. SG Rupasinghe H Duan HL Frericks Schmidt DA Berthold CM Rienstra MA Schuler 2007 Biochim Biophys Acta 1768 3061 3070
99. L Banci I Bertini S Marconi R Pierattelli 1993 Eur J Biochem 215 431 437
100. L Banci I Bertini S Marconi R Pierattelli SG Sligar 1994 J Am Chem Soc 116 4866 4873
101. JY Wei TC Pochapsky SS Pochapsky 2005 J Am Chem Soc 127 6974 6976
102. S Poli-Scaife R Attias PM Dansette D Mansuy 1997 Biochemistry 36 12672 12682
103. AG Roberts MD Diaz JN Lampe LM Shireman JS Grinstead MJ Dabrowski JT Pearson MK Bowman WM Atkins AP Campbell 2006 Biochemistry 45 1673 1684
104. KK Khan H Liu JR Halpert 2003 Drug Metab Dispos 31 356 359
105. K Liu D Ryan K Nakanishi A [tmp] McDermott 1995 J Am Chem Soc 117 6897 6906
106. K Liu J Williams H Lee MM Fitzgerald GM Jensen DB Goodin AE [tmp] McDermott 1998 J Am Chem Soc 120 10199 10202
107. F Castellani B van Rossum A Diehl M Schubert K Rehbein H Oschkinat 2002 Nature 420 98 102
108. H Lee PR Ortiz de Montellano AE [tmp] McDermott 1999 Biochemistry 38 10808 10813
109. TG Myers KE Thummel TF Kalhorn SD Nelson 1994 J Med Chem 37 860 867
110. R van de Straat J de Vries HJR de Boer RM Vromans NPE Vermeulen 1987 Xenobiotica 17 1 9
111. KA Regal SD Nelson 2000 Arch Biochem Biophys 384 47 58
112. MA Hummel PM Gannett JS Aguilar TS Tracy 2004 Biochemistry 43 7207 7214
113. Cameron MD, Wen B, Allen KE, Roberts AG, Schuman JT, Campbell AP, Kunze KL, Nelson SD (2005) Biochemistry 44: -1414314151
114. Jovanovic T, McDermott AE (2005) In: International conference cytochromes P450, proceedings, 14th, Dallas, TX, United States, May 31-June 5, 2005, pp 25-28
115. T Jovanovic AE [tmp] McDermott 2005 J Am Chem Soc 127 13816 13821
116. NR Orme-Johnson WH Orme-Johnson 1978 Methods Enzymol 52 252 257
117. W Cammer JB Schemkman RW Estabrook 1966 Biochem Biophys Res Commun 23 264 268
118. TG Spiro CA Grygon 1988 J Mol Struct 173 79 90
119. PM Champion BR Stallard GC Wagner IC Gunsalus 1982 J Am Chem Soc 104 5469 5472
120. WA Kalsbeck A Ghosh RK Pandey KM Smith DF Bocian 1995 J Am Chem Soc 117 10959 10968
121. P Anzenbacher J Hudecek 2001 J Inorg Biochem 87 209 213
122. P Hildebrandt G Heibel P Anzenbacher R Lange V Krüger A Stier 1994 Biochemistry 33 12920 12929
123. T Deng LM Proniewicz JR Kincaid 1999 Biochemistry 38 13699 13706
124. T Tosha N Kagawa T Ohta S Yoshioka MR Waterman T Kitagawa 2006 Biochemistry 45 5631 5640
125. PJ Mak S-C Im H Zhang LA Waskell JR Kincaid 2008 Biochemistry 47 3950 3963
126. A Bonifacio PHJ Keizers JNM Commandeur NPE Vermeulen B Robert C Gooijer G Van der Zwan 2006 Biochem Biophys Res Commun 343 772 779
127. T Tosha N Kagawa M Arase MR Waterman T Kitagawa 2008 J Biol Chem 283 3708 3717
128. S Todorovic C Jung P Hildebrandt DH Murgida 2006 J Biol Inorg Chem 11 119 127
129. WE Smith 1993 Methods Enzymol 226 482 495
130. AJ Haes RP Van Duyne 2002 J Am Chem Soc 124 10596 10604
131. JC Riboh AJ Haes AD [tmp] McFarland CR Yonzon RP Van Duyne 2003 J Phys Chem B 107 1772 1780
132. J Zhao A Das X Zhang GC Schatz SG Sligar RP Van Duyne 2006 J Am Chem Soc 128 11004 11005
133. JT Pearson JJ Hill J Swank N Isoherranen KL Kunze WM Atkins 2006 Biochemistry 45 6341 6353
134. MW Freyer EA Lewis 2008 Methods Cell Biol 84 79 113
135. A Velazquez Campoy E Freire 2005 Biophys Chem 115 115 124
136. A Ababou JE Ladbury 2007 J Mol Recognit 20 4 14
137. JE Ladbury 2004 BioTechniques 37 885 887
138. BK Muralidhara JR Halpert 2007 Drug Metab Rev 39 539 556
139. BK Muralidhara L Sun S Negi JR Halpert 2008 J Mol Biol 377 232 245
140. Y Zhao MA White BK Muralidhara L Sun JR Halpert CD Stout 2006 J Biol Chem 281 5973 5981
141. N Greenfield GD Fasman 1969 Biochemistry 8 4108 4116
142. SM Kelly TJ Jess NC Price 2005 Biochim Biophys Acta 1751 119 139
143. JH Dawson JR Trudell RE Linder G Barth E Bunnenberg C Djerassi 1978 Biochemistry 17 33 42
144. T Shimizu T Iizuka H Shimada Y Ishimura T Nozawa M Hatano 1981 Biochim Biophys Acta 670 341 354
145. M Sono JH Dawson 1982 J Biol Chem 257 5496 5502
146. LA Andersson AK Johnson JA Peterson 1997 Arch Biochem Biophys 345 79 87
147. M Sono R Perera S Jin TM Makris SG Sligar TA Bryson JH Dawson 2005 Arch Biochem Biophys 436 40 49
148. F Bancel G Hui Bon Hoa P Anzenbacher C Balny R Lange 2002 Methods Enzymol 357 145 157
149. G Hui Bon Hoa MA [tmp] McLean SG Sligar 2002 Biochim Biophys Acta Protein Struct Mol 1595 297 308
150. C Jung 2002 Biochim Biophys Acta 1595 309 328
151. MT Fisher SF Scarlata SG Sligar 1985 Arch Biochem Biophys 240 456 463
152. C Jung G Hui Bon Hoa D Davydov E Gill K Heremans 1995 Eur J Biochem 233 600 606
153. H Schulze O Ristau C Jung 1994 Eur J Biochem 224 1047 1055
154. M Unno K Ishimori Y Ishimura I Morishima 1994 Biochemistry 33 9762 9768
155. F Mitani T Iizuka H Shimada R Ueno Y Ishimura 1985 J Biol Chem 260 12042 12048
156. R Lange I Heiber-Langer C Bonfils I Fabre M Negishi C Balny 1994 Biophys J 66 89 98
157. DR Davydov JR Halpert J-P Renaud G Hui Bon Hoa 2003 Biochem Biophys Res Commun 312 121 130
158. DR Davydov BJ Baas SG Sligar JR Halpert 2007 Biochemistry 46 7852 7864
159. TL Poulos BC Finzel IC Gunsalus GC Wagner J Kraut 1985 J Biol Chem 260 16122 16130
160. TL Poulos BC Finzel AJ Howard 1987 J Mol Biol 195 687 700
161. TL Poulos BC Finzel AJ Howard 1986 Biochemistry 25 5314 5322
162. TL Poulos 2003 Proc Natl Acad Sci USA 100 13121 13122
163. JR Cupp-Vickery H Li TL Poulos 1994 Proteins 20 197 201
164. JR Cupp-Vickery TL Poulos 1995 Struct Biol 2 144 153
165. JR Cupp-Vickery TL Poulos 1997 Steroids 62 112 116
166. EE Scott JR Halpert 2005 Trends Biochem Sci 30 5 7
167. MR Wester EF Johnson C Marques-Soares PM Dansette D Mansuy CD Stout 2003 Biochemistry 42 6370 6379
168. MR Wester EF Johnson C Marques-Soares S Dijols PM Dansette D Mansuy CD Stout 2003 Biochemistry 42 9335 9345
169. PA Williams J Cosme A Ward HC Angove D Matak Vinkovic H Jhoti 2003 Nature 424 464 468
170. MR Wester JK Yano GA Schoch C Yang KJ Griffin CD Stout EF Johnson 2004 J Biol Chem 279 35630 35637
171. GA Schoch JK Yano MR Wester KJ Griffin CD Stout EF Johnson 2004 J Biol Chem 279 9497 9503
172. JK Yano MH Hsu KJ Griffin CD Stout EF Johnson 2005 Nat Struct Biol 12 822 823
173. S Sansen M-H Hsu CD Stout EF Johnson 2007 Arch Biochem Biophys 464 197 206
174. S Sansen JK Yano RL Reynald G Schoch K Griffin CD Stout EF Johnson 2007 J Biol Chem 282 14348 14355
175. BK Muralidhara S Negi CC Chin W Braun JR Halpert 2006 J Biol Chem 281 8051 8061
176. Z Wu LM Podust FP Guengerich 2005 J Biol Chem 280 41090 41100
177. FP Guengerich 2006 Proc Natl Acad Sci USA 103 13565 13566
178. Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, Johnson EF (2004) J Biol Chem 38091-38094
179. JM Hutzler MJ Hauer TS Tracy 2001 Drug Metab Dispos 29 1029 1034
180. JM Hutzler LC Wienkers JL Wahlstrom TJ Carlson TS Tracy 2003 Arch Biochem Biophys 410 16 24
181. MJ de Groot 2006 Drug Discov Today 11 601 606
182. DFV Lewis 2005 Expert Opin Drug Metab Toxicol 1 5 8
183. MJ Sykes RA [tmp] McKinnon JO Miners 2008 J Med Chem 51 780 791
184. I Zamora L Afzelius G Cruciani 2003 J Med Chem 46 2313 2324
185. D Zhou L Afzelius SW Grimm TB Andersson RJ Zauhar I Zamora 2006 Drug Metab Dispos 34 976 983
186. L Afzelius CH Arnby A Broo L Carlsson C Isaksson U Jurva B Kjellander K Kolmodin K Nilsson F Raubacher L Weidolf 2007 Drug Metab Rev 39 61 86
187. G Caron G Ermondi B Testa 2007 Pharm Res 24 480 501
188. D Fishelovitch C Hazan S Shaik HJ Wolfson R Nussinov 2007 J Am Chem Soc 129 1602 1611
189. DL Harris JY Park L Gruenke L Waskell 2004 Proteins 55 895 914
190. V Cojocaru PJ Winn RC Wade 2007 Biochim Biophys Acta 1770 390 401
191. SK Lüdemann V Lounnas RC Wade 2000 J Mol Biol 303 797 811
192. SK Lüdemann V Lounnas RC Wade 2000 J Mol Biol 303 813 830
193. PJ Winn SK Ludemann R Gauges V Lounnas RC Wade 2002 Proc Natl Acad Sci USA 99 5361 5366
194. RC Wade PJ Winn I Schlichting Sudarko 2004 J Inorg Biochem 98 1175 1182
195. K Schleinkofer Sudarko PJ Winn S Luedemann RC Wade 2005 EMBO Rep 6 584 589
196. H Remmer J Schenkman RW Estabrook H Sasame J Gillette S Narasimhulu DY Cooper O Rosenthal 1966 Mol Pharmacol 2 187 190