Skip to main content
SpringerLink
Log in

Substrate binding to cytochromes P450

  • Review
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

P450s have attracted tremendous attention owing to not only their involvement in the metabolism of drug molecules and endogenous substrates but also the unusual nature of the reaction they catalyze, namely, the oxidation of unactivated C–H bonds. The binding of substrates to P450s, which is usually viewed as the first step in the catalytic cycle, has been studied extensively via a variety of biochemical and biophysical approaches. These studies were directed towards answering different questions related to P450s, including mechanism of oxidation, substrate properties, unusual substrate oxidation kinetics, function, and active-site features. Some of the substrate binding studies extending over a period of more than 40 years of dedicated work have been summarized in this review and categorized by the techniques employed in the binding studies.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

Notes

  1. The term “absorbance silent” refers to a substrate–P450 interaction that does not involve a change in heme Soret spectra and therefore cannot be detected by absorption spectroscopy.

  2. The term “thermodynamic signatures” is used by the authors to describe plots characterizing the thermodynamic parameters (free energy, enthalpy, and entropy) associated with the binding of a particular ligand.

Abbreviations

αNF:

α-naphthoflavone

CD:

circular dichroism

EPR:

electron paramagnetic resonance

FRET:

Förster resonance energy transfer

HSQC:

heteronuclear single quantum coherence

ITC:

isothermal titration calorimetry

SAM:

self-assembled monolayer

References

  1. Guengerich FP (1994) Toxicol Lett 70:133–138

    Article  CAS  Google Scholar 

  2. Ortiz de Montellano PR (2005) Cytochrome P450: structure, mechanism, and biochemistry, 3rd edn. Kluwer/Plenum, New York

    Google Scholar 

  3. Denisov IG, Makris TM, Sligar SG, Schlichting I (2005) Chem Rev 105:2253–2277

    Article  CAS  Google Scholar 

  4. Guengerich FP (2008) Chem Res Toxicol 21:70–83

    Article  CAS  Google Scholar 

  5. Lewis DFV, Ito Y, Goldfarb PS (2006) Drug Dev Res 66:19–24

    Article  CAS  Google Scholar 

  6. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, Gunsalus IC, Nebert DW (1996) Pharmacogenetics 6:1–42

    Article  CAS  Google Scholar 

  7. Katagiri M, Ganguli BN, Gunsalus IC (1968) J Biol Chem 243:3543–3546

    CAS  Google Scholar 

  8. Sligar SG, Gunsalus IC (1976) Proc Natl Acad Sci USA 73:1078–1082

    Article  CAS  Google Scholar 

  9. Tyson CA, Lipscomb JD, Gunsalus IC (1972) J Biol Chem 247:5777–5784

    CAS  Google Scholar 

  10. Poulos TL, Raag R (1992) FASEB J 6:674–679

    CAS  Google Scholar 

  11. Guengerich FP, Macdonald TL (1984) Acc Chem Res 17:9–16

    Article  CAS  Google Scholar 

  12. Guengerich FP (2001) Chem Res Toxicol 14:611–650

    Article  CAS  Google Scholar 

  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

    Google Scholar 

  14. Stark K, Guengerich FP (2007) Drug Metab Rev 39:627–637

    Article  CAS  Google Scholar 

  15. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE (2004) Drug Metab Dispos 32:1201–1208

    Article  CAS  Google Scholar 

  16. Wienkers LC, Heath TG (2005) Nat Rev Drug Discov 4:825–833

    Article  CAS  Google Scholar 

  17. Nebert DW, Russell DW (2002) Lancet 360:1155–1162

    Article  CAS  Google Scholar 

  18. Isin EM, Guengerich FP (2006) Biochim Biophys Acta 1770:314–329

    Google Scholar 

  19. Guengerich FP, Isin EM (2008) Acta Chem Sloven 55:7–19

    CAS  Google Scholar 

  20. Yun C-H, Kim K-H, Calcutt MW, Guengerich FP (2005) J Biol Chem 280:12279–12291

    Article  CAS  Google Scholar 

  21. Isin EM, Guengerich FP (2006) J Biol Chem 281:9127–9136

    Article  CAS  Google Scholar 

  22. Schenkman JB, Remmer H, Estabrook RW (1967) Mol Pharmacol 3:113–123

    CAS  Google Scholar 

  23. Sharrock M, Muenck E, Debrunner PG, Marshall V, Lipscomb JD, Gunsalus IC (1973) Biochemistry 12:258–265

    Article  CAS  Google Scholar 

  24. Daff SN, Chapman SK, Turner KL, Holt RA, Govindaraj S, Poulos TL, Munro AW (1997) Biochemistry 36:13816–13823

    Article  CAS  Google Scholar 

  25. Aguey-Zinsou K-F, Bernhardt PV, De Voss JJ, Slessor KE (2003) Chem Commun 418–419

  26. Guengerich FP (1983) Biochemistry 22:2811–2820

    Article  CAS  Google Scholar 

  27. Backes WL, Sligar SG, Schenkman JB (1982) Biochemistry 21:1324–1330

    Article  CAS  Google Scholar 

  28. Huang YY, Hara T, Sligar S, Coon MJ, Kimura T (1986) Biochemistry 25:1390–1394

    Article  CAS  Google Scholar 

  29. Backes WL, Eyer CS (1989) J Biol Chem 264:6252–6259

    CAS  Google Scholar 

  30. Yamazaki H, Johnson WW, Ueng Y-F, Shimada T, Guengerich FP (1996) J Biol Chem 271:27438–27444

    Article  CAS  Google Scholar 

  31. Guengerich FP, Johnson WW (1997) Biochemistry 36:14741–14750

    Article  CAS  Google Scholar 

  32. Fersht A (1999) Structure and mechanism in protein science. Freeman, New York

    Google Scholar 

  33. Das A, Grinkova YV, Sligar SG (2007) J Am Chem Soc 129:13778–13779

    Article  CAS  Google Scholar 

  34. Hosea NA, Miller GP, Guengerich FP (2000) Biochemistry 39:5929–5939

    Article  CAS  Google Scholar 

  35. Isin EM, Guengerich FP (2007) J Biol Chem 282:6863–6874

    Article  CAS  Google Scholar 

  36. Griffin BW, Peterson JA (1972) Biochemistry 11:4740–4746

    Article  CAS  Google Scholar 

  37. Chun Y-J, Shimada T, Sanchez-Ponz R, Martin MV, Lei L, Zhao B, Kelly SL, Waterman MR, Lamb DC, Guengerich FP (2007) J Biol Chem 282:17486–17500

    Article  CAS  Google Scholar 

  38. Roberts AG, Atkins WM (2007) Arch Biochem Biophys 463:89–101

    Article  CAS  Google Scholar 

  39. Denisov IG, Baas BJ, Grinkova YV, Sligar SG (2007) J Biol Chem 282:7066–7076

    Article  CAS  Google Scholar 

  40. Yoon M-Y, Campbell AP, Atkins WM (2004) Drug Metab Rev 36:219–230

    Article  CAS  Google Scholar 

  41. Sohl CD, Isin EM, Eoff RL, Marsch GA, Stec DF, Guengerich FP (2008) J Biol Chem 283:7293–7308

    Article  CAS  Google Scholar 

  42. Fernando H, Halpert JR, Davydov DR (2006) Biochemistry 45:4199–4209

    Article  CAS  Google Scholar 

  43. Cupp-Vickery J, Anderson R, Hatziris Z (2000) Proc Natl Acad Sci USA 97:3050–3055

    Article  CAS  Google Scholar 

  44. Zhao B, Lamb DC, Lei L, Kelly SL, Yuan H, Hachey DL, Waterman MR (2007) Biochemistry 46:8725–8733

    Article  CAS  Google Scholar 

  45. Zhao B, Guengerich FP, Bellamine A, Lamb DC, Izumikawa M, Funa N, Lei L, Podust LM, Sundamoorthy M, Reddy LM, Kelly SL, Stec D, Voehler M, Falck JR, Moore BS, Shimada T, Waterman MR (2005) J Biol Chem 280:11599–11607

    Article  CAS  Google Scholar 

  46. Ekroos M, Sjögren T (2006) Proc Nat Acad Sci USA 103:13682–13687

    Article  CAS  Google Scholar 

  47. Johnson EF, Stout CD (2005) Biochem Biophys Res Commun 338:331–336

    Article  CAS  Google Scholar 

  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

    Google Scholar 

  49. Otyepka M, Skopalik J, Anzenbacherova E, Anzenbacher P (2007) Biochim Biophys Acta 1770:376–389

    CAS  Google Scholar 

  50. Leibman KC, Hildebrandt AG, Estabrook RW (1969) Biochem Biophys Res Commun 36:789–794

    Article  CAS  Google Scholar 

  51. Mitani F, Horie S (1969) J Biochem 66:139–149

    CAS  Google Scholar 

  52. Jefcoate CR (1978) Methods Enzymol 52:258–279

    Article  CAS  Google Scholar 

  53. Lewis DF (2003) Arch Biochem Biophys 409:32–44

    Article  CAS  Google Scholar 

  54. Atkins WM (2006) Expert Opin Drug Metab Toxicol 2:573–579

    Article  CAS  Google Scholar 

  55. Ueng Y-F, Kuwabara T, Chun Y-J, Guengerich FP (1997) Biochemistry 36:370–381

    Article  CAS  Google Scholar 

  56. Tracy TS (2006) Drugs R D 7:349–363

    Article  CAS  Google Scholar 

  57. Guengerich FP (1999) Annu Rev Pharmacol Toxicol 39:1–17

    Article  CAS  Google Scholar 

  58. Harlow GR, Halpert JR (1998) Proc Natl Acad Sci USA 95:6636–6641

    Article  CAS  Google Scholar 

  59. Roberts AG, Campbell AP, Atkins WM (2005) Biochemistry 44:1353–1366

    Article  CAS  Google Scholar 

  60. Cameron MD, Wen B, Roberts AG, Atkins WM, Campbell AP, Nelson SD (2007) Chem Res Toxicol 20:1434–1441

    Article  CAS  Google Scholar 

  61. Davydov DR, Fernando H, Halpert JR (2006) Biophys Chem 123:95–101

    Article  CAS  Google Scholar 

  62. Job P (1928) Ann Chim Appl 9:113–203

    CAS  Google Scholar 

  63. Facchiano A, Ragone R (2003) Anal Biochem 313:170–172

    Article  CAS  Google Scholar 

  64. Baas BJ, Denisov IG, Sligar SG (2004) Arch Biochem Biophys 430:218–228

    Article  CAS  Google Scholar 

  65. Nath A, Grinkova YV, Sligar SG, Atkins WM (2007) J Biol Chem 282:28309–28320

    Article  CAS  Google Scholar 

  66. Venkatakrishnan K, Von Moltke LL, Greenblatt DJ (1998) J Pharm Sci 87:1502–1507

    Article  CAS  Google Scholar 

  67. Miller GP, Guengerich FP (2001) Biochemistry 40:7262–7272

    Article  CAS  Google Scholar 

  68. Isin EM, Sohl CD, Eoff RL, Guengerich FP (2008) Arch Biochem Biophys 473:69–75

    Article  CAS  Google Scholar 

  69. Burleigh BD Jr, Foust GP, Williams CH Jr (1969) Anal Biochem 27:536–544

    Article  CAS  Google Scholar 

  70. Foust GP, Burleigh BD Jr, Mayhew SG, Williams CH Jr, Massey V (1969) Anal Biochem 27:530–535

    Article  CAS  Google Scholar 

  71. Guengerich FP, Krauser JA, Johnson WW (2004) Biochemistry 43:10775–10788

    Article  CAS  Google Scholar 

  72. Walsh C (1979) Enzymatic reaction mechanisms. Freeman, San Francisco

    Google Scholar 

  73. Yao H, McCullough CR, Costache AD, Pullela PK, Sem DS (2007) Proteins Struct Funct Bioinf 69:125–138

    Article  CAS  Google Scholar 

  74. Lakowicz JR (1999) Principles of fluorescence spectroscopy. Kluwer/Plenum, New York

    Google Scholar 

  75. Sandhu P, Guo Z, Baba T, Martin MV, Tukey RH, Guengerich FP (1994) Arch Biochem Biophys 309:168–177

    Article  CAS  Google Scholar 

  76. Weber G, Teale FJW (1959) Discuss Faraday Soc 27:134–141

    Article  Google Scholar 

  77. Förster T (1969) Angew Chem Int Ed Engl 8:333–343

    Article  Google Scholar 

  78. Lehrer SS (1997) Methods Enzymol 278:286–295

    Article  CAS  Google Scholar 

  79. Dabrowski MJ, Schrag ML, Wienkers LC, Atkins WM (2002) J Am Chem Soc 124:11866–11867

    Article  CAS  Google Scholar 

  80. Davydov DR, Kumar S, Halpert JR (2002) Biochem Biophys Res Commun 294:806–812

    Article  CAS  Google Scholar 

  81. Williams PA, Cosme J, Vinkovic DM, Ward A, Angove HC, Day PJ, Vonrhein C, Tickle IJ, Jhoti H (2004) Science 305:683–686

    Article  CAS  Google Scholar 

  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. Prasad S, Mazumdar S, Mitra S (2000) FEBS Lett 477:157–160

    Article  CAS  Google Scholar 

  84. Prasad S, Mitra S (2002) Biochemistry 41:14499–14508

    Article  CAS  Google Scholar 

  85. Stortelder A, Keizers PHJ, Oostenbrink C, De Graaf C, De Kruijf P, Vermeulen NPE, Gooijer C, Commandeur JNM, Van der Zwan G (2006) Biochem J 393:635–643

    Article  CAS  Google Scholar 

  86. Lampe JN, Atkins WM (2006) Biochemistry 45:12204–1221

    Article  CAS  Google Scholar 

  87. Lampe JN, Fernandez C, Nath A, Atkins WM (2008) Biochemistry 47:509–516

    Article  CAS  Google Scholar 

  88. Stryer L (1965) J Mol Biol 13:482–495

    Article  CAS  Google Scholar 

  89. Chougnet A, Stoessel C, Woggon W-D (2003) Bioorg Med Chem Lett 13:3643–3645

    Article  CAS  Google Scholar 

  90. Chougnet A, Grinkova Y, Ricard D, Sligar S, Woggon W-D (2007) ChemMedChem 2:717–724

    Article  CAS  Google Scholar 

  91. Sackett DL, Wolff J (1987) Anal Biochem 167:228–234

    Article  CAS  Google Scholar 

  92. Davydov DR, Botchkareva AE, Davydova NE, Halpert JR (2005) Biophys J 89:418–432

    Article  CAS  Google Scholar 

  93. Tsalkova TN, Davydova NY, Halpert JR, Davydov DR (2007) Biochemistry 46:106–119

    Article  CAS  Google Scholar 

  94. Shuker SB, Hajduk PJ, Meadows RP, Fesik SW (1996) Science 274:1531–1534

    Article  CAS  Google Scholar 

  95. Medek A, Olejniczak ET, Meadows RP, Fesik SW (2000) J Biomol NMR 18:229–238

    Article  CAS  Google Scholar 

  96. Pochapsky TC, Kostic M, Jain N, Pejchal R (2001) Biochemistry 40:5602–5614

    Article  CAS  Google Scholar 

  97. Marley J, Lu M, Bracken C (2001) J Biomol NMR 20:71–75

    Article  CAS  Google Scholar 

  98. Rupasinghe SG, Duan H, Frericks Schmidt HL, Berthold DA, Rienstra CM, Schuler MA (2007) Biochim Biophys Acta 1768:3061–3070

    Article  CAS  Google Scholar 

  99. Banci L, Bertini I, Marconi S, Pierattelli R (1993) Eur J Biochem 215:431–437

    Article  CAS  Google Scholar 

  100. Banci L, Bertini I, Marconi S, Pierattelli R, Sligar SG (1994) J Am Chem Soc 116:4866–4873

    Article  CAS  Google Scholar 

  101. Wei JY, Pochapsky TC, Pochapsky SS (2005) J Am Chem Soc 127:6974–6976

    Article  CAS  Google Scholar 

  102. Poli-Scaife S, Attias R, Dansette PM, Mansuy D (1997) Biochemistry 36:12672–12682

    Article  CAS  Google Scholar 

  103. Roberts AG, Diaz MD, Lampe JN, Shireman LM, Grinstead JS, Dabrowski MJ, Pearson JT, Bowman MK, Atkins WM, Campbell AP (2006) Biochemistry 45:1673–1684

    Article  CAS  Google Scholar 

  104. Khan KK, Liu H, Halpert JR (2003) Drug Metab Dispos 31:356–359

    Article  CAS  Google Scholar 

  105. Liu K, Ryan D, Nakanishi K, McDermott A (1995) J Am Chem Soc 117:6897–6906

    Article  CAS  Google Scholar 

  106. Liu K, Williams J, Lee H, Fitzgerald MM, Jensen GM, Goodin DB, McDermott AE (1998) J Am Chem Soc 120:10199–10202

    Article  CAS  Google Scholar 

  107. Castellani F, van Rossum B, Diehl A, Schubert M, Rehbein K, Oschkinat H (2002) Nature 420:98–102

    Article  CAS  Google Scholar 

  108. Lee H, Ortiz de Montellano PR, McDermott AE (1999) Biochemistry 38:10808–10813

    Article  CAS  Google Scholar 

  109. Myers TG, Thummel KE, Kalhorn TF, Nelson SD (1994) J Med Chem 37:860–867

    Article  CAS  Google Scholar 

  110. van de Straat R, de Vries J, de Boer HJR, Vromans RM, Vermeulen NPE (1987) Xenobiotica 17:1–9

    Google Scholar 

  111. Regal KA, Nelson SD (2000) Arch Biochem Biophys 384:47–58

    Article  CAS  Google Scholar 

  112. Hummel MA, Gannett PM, Aguilar JS, Tracy TS (2004) Biochemistry 43:7207–7214

    Article  CAS  Google Scholar 

  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. Jovanovic T, McDermott AE (2005) J Am Chem Soc 127:13816–13821

    Article  CAS  Google Scholar 

  116. Orme-Johnson NR, Orme-Johnson WH (1978) Methods Enzymol 52:252–257

    Article  CAS  Google Scholar 

  117. Cammer W, Schemkman JB, Estabrook RW (1966) Biochem Biophys Res Commun 23:264–268

    Article  CAS  Google Scholar 

  118. Spiro TG, Grygon CA (1988) J Mol Struct 173:79–90

    Article  CAS  Google Scholar 

  119. Champion PM, Stallard BR, Wagner GC, Gunsalus IC (1982) J Am Chem Soc 104:5469–5472

    Article  CAS  Google Scholar 

  120. Kalsbeck WA, Ghosh A, Pandey RK, Smith KM, Bocian DF (1995) J Am Chem Soc 117:10959–10968

    Article  CAS  Google Scholar 

  121. Anzenbacher P, Hudecek J (2001) J Inorg Biochem 87:209–213

    Article  CAS  Google Scholar 

  122. Hildebrandt P, Heibel G, Anzenbacher P, Lange R, Krüger V, Stier A (1994) Biochemistry 33:12920–12929

    Article  CAS  Google Scholar 

  123. Deng T, Proniewicz LM, Kincaid JR (1999) Biochemistry 38:13699–13706

    Article  CAS  Google Scholar 

  124. Tosha T, Kagawa N, Ohta T, Yoshioka S, Waterman MR, Kitagawa T (2006) Biochemistry 45:5631–5640

    Article  CAS  Google Scholar 

  125. Mak PJ, Im S-C, Zhang H, Waskell LA, Kincaid JR (2008) Biochemistry 47:3950–3963

    Article  CAS  Google Scholar 

  126. Bonifacio A, Keizers PHJ, Commandeur JNM, Vermeulen NPE, Robert B, Gooijer C, Van der Zwan G (2006) Biochem Biophys Res Commun 343:772–779

    CAS  Google Scholar 

  127. Tosha T, Kagawa N, Arase M, Waterman MR, Kitagawa T (2008) J Biol Chem 283:3708–3717

    Article  CAS  Google Scholar 

  128. Todorovic S, Jung C, Hildebrandt P, Murgida DH (2006) J Biol Inorg Chem 11:119–127

    Article  CAS  Google Scholar 

  129. Smith WE (1993) Methods Enzymol 226:482–495

    Article  CAS  Google Scholar 

  130. Haes AJ, Van Duyne RP (2002) J Am Chem Soc 124:10596–10604

    Article  CAS  Google Scholar 

  131. Riboh JC, Haes AJ, McFarland AD, Yonzon CR, Van Duyne RP (2003) J Phys Chem B 107:1772–1780

    Article  CAS  Google Scholar 

  132. Zhao J, Das A, Zhang X, Schatz GC, Sligar SG, Van Duyne RP (2006) J Am Chem Soc 128:11004–11005

    Article  CAS  Google Scholar 

  133. Pearson JT, Hill JJ, Swank J, Isoherranen N, Kunze KL, Atkins WM (2006) Biochemistry 45:6341–6353

    Article  CAS  Google Scholar 

  134. Freyer MW, Lewis EA (2008) Methods Cell Biol 84:79–113

    Article  CAS  Google Scholar 

  135. Velazquez Campoy A, Freire E (2005) Biophys Chem 115:115–124

    Article  CAS  Google Scholar 

  136. Ababou A, Ladbury JE (2007) J Mol Recognit 20:4–14

    Article  CAS  Google Scholar 

  137. Ladbury JE (2004) BioTechniques 37:885–887

    CAS  Google Scholar 

  138. Muralidhara BK, Halpert JR (2007) Drug Metab Rev 39:539–556

    Article  CAS  Google Scholar 

  139. Muralidhara BK, Sun L, Negi S, Halpert JR (2008) J Mol Biol 377:232–245

    Article  CAS  Google Scholar 

  140. Zhao Y, White MA, Muralidhara BK, Sun L, Halpert JR, Stout CD (2006) J Biol Chem 281:5973–5981

    Article  CAS  Google Scholar 

  141. Greenfield N, Fasman GD (1969) Biochemistry 8:4108–4116

    Article  CAS  Google Scholar 

  142. Kelly SM, Jess TJ, Price NC (2005) Biochim Biophys Acta 1751:119–139

    CAS  Google Scholar 

  143. Dawson JH, Trudell JR, Linder RE, Barth G, Bunnenberg E, Djerassi C (1978) Biochemistry 17:33–42

    Article  CAS  Google Scholar 

  144. Shimizu T, Iizuka T, Shimada H, Ishimura Y, Nozawa T, Hatano M (1981) Biochim Biophys Acta 670:341–354

    CAS  Google Scholar 

  145. Sono M, Dawson JH (1982) J Biol Chem 257:5496–5502

    CAS  Google Scholar 

  146. Andersson LA, Johnson AK, Peterson JA (1997) Arch Biochem Biophys 345:79–87

    Article  CAS  Google Scholar 

  147. Sono M, Perera R, Jin S, Makris TM, Sligar SG, Bryson TA, Dawson JH (2005) Arch Biochem Biophys 436:40–49

    Article  CAS  Google Scholar 

  148. Bancel F, Hui Bon Hoa G, Anzenbacher P, Balny C, Lange R (2002) Methods Enzymol 357:145–157

    Article  CAS  Google Scholar 

  149. Hui Bon Hoa G, McLean MA, Sligar SG (2002) Biochim Biophys Acta Protein Struct Mol 1595:297–308

    CAS  Google Scholar 

  150. Jung C (2002) Biochim Biophys Acta 1595:309–328

    CAS  Google Scholar 

  151. Fisher MT, Scarlata SF, Sligar SG (1985) Arch Biochem Biophys 240:456–463

    Article  CAS  Google Scholar 

  152. Jung C, Hui Bon Hoa G, Davydov D, Gill E, Heremans K (1995) Eur J Biochem 233:600–606

    Article  CAS  Google Scholar 

  153. Schulze H, Ristau O, Jung C (1994) Eur J Biochem 224:1047–1055

    Article  CAS  Google Scholar 

  154. Unno M, Ishimori K, Ishimura Y, Morishima I (1994) Biochemistry 33:9762–9768

    Article  CAS  Google Scholar 

  155. Mitani F, Iizuka T, Shimada H, Ueno R, Ishimura Y (1985) J Biol Chem 260:12042–12048

    CAS  Google Scholar 

  156. Lange R, Heiber-Langer I, Bonfils C, Fabre I, Negishi M, Balny C (1994) Biophys J 66:89–98

    CAS  Google Scholar 

  157. Davydov DR, Halpert JR, Renaud J-P, Hui Bon Hoa G (2003) Biochem Biophys Res Commun 312:121–130

    Article  CAS  Google Scholar 

  158. Davydov DR, Baas BJ, Sligar SG, Halpert JR (2007) Biochemistry 46:7852–7864

    Article  CAS  Google Scholar 

  159. Poulos TL, Finzel BC, Gunsalus IC, Wagner GC, Kraut J (1985) J Biol Chem 260:16122–16130

    CAS  Google Scholar 

  160. Poulos TL, Finzel BC, Howard AJ (1987) J Mol Biol 195:687–700

    Article  CAS  Google Scholar 

  161. Poulos TL, Finzel BC, Howard AJ (1986) Biochemistry 25:5314–5322

    Article  CAS  Google Scholar 

  162. Poulos TL (2003) Proc Natl Acad Sci USA 100:13121–13122

    Article  CAS  Google Scholar 

  163. Cupp-Vickery JR, Li H, Poulos TL (1994) Proteins 20:197–201

    Article  CAS  Google Scholar 

  164. Cupp-Vickery JR, Poulos TL (1995) Struct Biol 2:144–153

    Article  CAS  Google Scholar 

  165. Cupp-Vickery JR, Poulos TL (1997) Steroids 62:112–116

    Article  CAS  Google Scholar 

  166. Scott EE, Halpert JR (2005) Trends Biochem Sci 30:5–7

    Article  CAS  Google Scholar 

  167. Wester MR, Johnson EF, Marques-Soares C, Dansette PM, Mansuy D, Stout CD (2003) Biochemistry 42:6370–6379

    Article  CAS  Google Scholar 

  168. Wester MR, Johnson EF, Marques-Soares C, Dijols S, Dansette PM, Mansuy D, Stout CD (2003) Biochemistry 42:9335–9345

    Article  CAS  Google Scholar 

  169. Williams PA, Cosme J, Ward A, Angove HC, Matak Vinkovic D, Jhoti H (2003) Nature 424:464–468

    Article  CAS  Google Scholar 

  170. Wester MR, Yano JK, Schoch GA, Yang C, Griffin KJ, Stout CD, Johnson EF (2004) J Biol Chem 279:35630–35637

    Article  CAS  Google Scholar 

  171. Schoch GA, Yano JK, Wester MR, Griffin KJ, Stout CD, Johnson EF (2004) J Biol Chem 279:9497–9503

    Article  CAS  Google Scholar 

  172. Yano JK, Hsu MH, Griffin KJ, Stout CD, Johnson EF (2005) Nat Struct Biol 12:822–823

    Article  CAS  Google Scholar 

  173. Sansen S, Hsu M-H, Stout CD, Johnson EF (2007) Arch Biochem Biophys 464:197–206

    Article  CAS  Google Scholar 

  174. Sansen S, Yano JK, Reynald RL, Schoch G, Griffin K, Stout CD, Johnson EF (2007) J Biol Chem 282:14348–14355

    Article  CAS  Google Scholar 

  175. Muralidhara BK, Negi S, Chin CC, Braun W, Halpert JR (2006) J Biol Chem 281:8051–8061

    Article  CAS  Google Scholar 

  176. Wu Z, Podust LM, Guengerich FP (2005) J Biol Chem 280:41090–41100

    Article  CAS  Google Scholar 

  177. Guengerich FP (2006) Proc Natl Acad Sci USA 103:13565–13566

    Article  CAS  Google Scholar 

  178. Yano JK, Wester MR, Schoch GA, Griffin KJ, Stout CD, Johnson EF (2004) J Biol Chem 38091–38094

  179. Hutzler JM, Hauer MJ, Tracy TS (2001) Drug Metab Dispos 29:1029–1034

    CAS  Google Scholar 

  180. Hutzler JM, Wienkers LC, Wahlstrom JL, Carlson TJ, Tracy TS (2003) Arch Biochem Biophys 410:16–24

    Article  Google Scholar 

  181. de Groot MJ (2006) Drug Discov Today 11:601–606

    Article  CAS  Google Scholar 

  182. Lewis DFV (2005) Expert Opin Drug Metab Toxicol 1:5–8

    Article  CAS  Google Scholar 

  183. Sykes MJ, McKinnon RA, Miners JO (2008) J Med Chem 51:780–791

    Article  CAS  Google Scholar 

  184. Zamora I, Afzelius L, Cruciani G (2003) J Med Chem 46:2313–2324

    Article  CAS  Google Scholar 

  185. Zhou D, Afzelius L, Grimm SW, Andersson TB, Zauhar RJ, Zamora I (2006) Drug Metab Dispos 34:976–983

    CAS  Google Scholar 

  186. Afzelius L, Arnby CH, Broo A, Carlsson L, Isaksson C, Jurva U, Kjellander B, Kolmodin K, Nilsson K, Raubacher F, Weidolf L (2007) Drug Metab Rev 39:61–86

    Article  CAS  Google Scholar 

  187. Caron G, Ermondi G, Testa B (2007) Pharm Res 24:480–501

    Article  CAS  Google Scholar 

  188. Fishelovitch D, Hazan C, Shaik S, Wolfson HJ, Nussinov R (2007) J Am Chem Soc 129:1602–1611

    Article  CAS  Google Scholar 

  189. Harris DL, Park JY, Gruenke L, Waskell L (2004) Proteins 55:895–914

    Article  CAS  Google Scholar 

  190. Cojocaru V, Winn PJ, Wade RC (2007) Biochim Biophys Acta 1770:390–401

    CAS  Google Scholar 

  191. Lüdemann SK, Lounnas V, Wade RC (2000) J Mol Biol 303:797–811

    Article  CAS  Google Scholar 

  192. Lüdemann SK, Lounnas V, Wade RC (2000) J Mol Biol 303:813–830

    Article  CAS  Google Scholar 

  193. Winn PJ, Ludemann SK, Gauges R, Lounnas V, Wade RC (2002) Proc Natl Acad Sci USA 99:5361–5366

    Article  CAS  Google Scholar 

  194. Wade RC, Winn PJ, Schlichting I, Sudarko (2004) J Inorg Biochem 98:1175–1182

    Article  CAS  Google Scholar 

  195. Schleinkofer K, Sudarko, Winn PJ, Luedemann S, Wade RC (2005) EMBO Rep 6:584–589

    Article  CAS  Google Scholar 

  196. Remmer H, Schenkman J, Estabrook RW, Sasame H, Gillette J, Narasimhulu S, Cooper DY, Rosenthal O (1966) Mol Pharmacol 2:187–190

    CAS  Google Scholar 

Download references

Acknowledgements

F.P.G. is suported by US Public Health Service grants R37 CA090426 and P30 ES000267. We thank W. Comstock for editorial assistance.

Author information

Authors and Affiliations

  1. Biotransformation Section, Department of Discovery DMPK & Bioanalytical Chemistry, AstraZeneca R & D Mölndal, 431 83, Mölndal, Sweden

    Emre M. Isin

  2. Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine, Nashville, TN, 37232-0146, USA

    F. Peter Guengerich

Authors
  1. Emre M. Isin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. F. Peter Guengerich
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Emre M. Isin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Isin, E.M., Guengerich, F.P. Substrate binding to cytochromes P450. Anal Bioanal Chem 392, 1019–1030 (2008). https://doi.org/10.1007/s00216-008-2244-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-008-2244-0

Keywords

Search

Navigation