Recent progress in cytochrome P450 enzyme electrochemistry

Expert Opinion on Drug Metabolism and Toxicology

Volumn 2, Issue 4, 2006, Pages 581-589

  Fleming, Barry D ^a   Johnson, Daniel L ^a   Bond, Alan M ^a   Martin, Lisandra L ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

Cytochrome P450; Electrochemistry; Enzyme; Immobilisation; Redox potential; Voltammetry

Indexed keywords

CYTOCHROME P450; IMMOBILIZED ENZYME;

BIOPROCESS; ELECTROCHEMISTRY; ELECTRODE; ELECTRON TRANSPORT; ENZYME MECHANISM; ENZYME SUBSTRATE; OXYGENATION; POTENTIOMETRIC TITRATION; POTENTIOMETRY; REVIEW; THERMODYNAMICS; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; PH;

CYTOCHROME P-450 ENZYME SYSTEM; ELECTROCHEMISTRY; ELECTRODES; ELECTRON TRANSPORT; ENZYMES, IMMOBILIZED; HUMANS; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR;

EID: 33747834364     PISSN: 17425255     EISSN: None     Source Type: Journal    
DOI: 10.1517/17425255.2.4.581     Document Type: Review

References (58)

1. ORTIZ DE MONTELLANO PR: Cytochrome P450: Structure, Mechanism, and Biochemistry. Kluwer Academic/Plenum Publishers, New York, USA (2005).
2. POULOS TL, JOHNSON EF: Structures of Cytochrome P450 Enzymes. In: Cytochrome P450: structure, mechanism, and biochemistry. PR Ortiz de Montellano (Ed.), Kluwer Academic/Plenum Publishers, New York, USA (2005):87-114.
3. BISTOLAS N, WOLLENBERGER U, JUNG C, SCHELLER FW: Cytochrome P450 biosensors - a review. Biosens. Bioelectron. (2005) 20(12):2408-2423.
4. SHUMYANTSEVA VV, BULKO TV, ARCHAKOV AI: Electrochemical reduction of cytochrome P450 as an approach to the construction of biosensors and bioreactors. J. Inorg. Biochem. (2005) 99:1051-1063.
5. UDIT AK, GRAY HB: Electrochemistry of heme-thiolate proteins. Biochem. Biophys. Res. Commun. (2005) 338:470-476.
6. RUSLING JF, NASSAR A-EF: Enhanced electron transfer for myoglobin in surfactant films on electrodes. J. Am. Chem. Soc. (1993) 115(25):11891-11897.
7. ZHANG Z, NASSAR A-EF, LU Z, SCHENKMAN JB, RUSLING JF: Direct electron injection from electrodes to cytochrome P450cam in biomembrane-like films. J. Chem. Soc. Faraday Trans. (1997) 93(9):1769-1774.
8. RUSLING JF: Enzyme bioelectrochemistry in cast biomembrame-like films. Acc. Chem. Res. (1998) 31(6):363-369.
9. CHEN X, HU N, ZENG Y, RUSLING JF, YANG J: Ordered electrochemically active films of hemoglobin, didodecylmethylammonium ions, and clay. Langmuir (1999) 15(20):7022-7030.
10. DJURICIC D, FLEMING BD, HILL HAO, TIAN Y: Towards exploiting the electrochemistry of cytochrome P450. In: Trends in Molecular Electrochemistry. AJL Pombeiro, C Amatore (Eds), Marcel Dekker, USA and FontisMedia SA, Switzerland (2004):189-208.
11. WIRTZ M, KLUCIK J, RIVERA M: Ferredoxin-mediated electrocatalytic dehalogenation of haloalkanes by cytochrome P450cam. J. Am. Chem. Soc. (2000) 122(6):1047-1056.
12. SCHELLER F, RENNEBERG R, SCHWARZE W et al.: Electrochemical investigations on the oxygen activation by cytochrome P450. Acta Biol. Med. Germ. (1979) 38(2-3):503-509.
13. FLEMING BD, TIAN Y, BELL SG et al.: Redox properties of cytochrome P450BM3 measured by direct methods. Eur. J. Biochem. (2003) 270:4082-4088.
14. UDIT AK, HILL MG, BITTNER VG, ARNOLD FH, GRAY HB: Reduction of dioxygen catalysed by pyrene-wired heme domain cytochrome P450 BM3 electrodes. J. Am. Chem. Soc. (2004) 126(33):10218-10219.
15. UDIT AK, HINDOYAN N, HILL MG, ARNOLD FH, GRAY HB: Protein-surfactant film voltammetry of wild-type and mutant cytochrome P450 BM3. Inorg. Chem. (2005) 44(12):4109-4111.
16. XUAN GS, JUNG S, KIM S: Electrocatalytic reduction of nitric oxide by cytochrome P450-modified gold electrodes. Bull. Korean Chem. Soc. (2004) 25(2):165-166.
17. LVOV YM, LUZ, SCHENKMAN JB, ZU X, RUSLING JF: Direct electrochemistry of myoglobin and cytochrome P450cam in alternate layer-by-layer films with DNA and other polyions. J. Am. Chem. Soc. (1998) 120(17):4073-4080.
18. MAYHEW MP, REIPA V, HOLDEN MJ, VILKER VL: Improving the cytochrome P450 enzyme system for electrode-driven biocatalysis of styrene epoxidation. Biotechnol. Prog. (2000) 16(4):610-616.
19. MUNGE B, ESTAVILLO C, SCHENKMAN JB, RUSLING JF: Optimisation of electrochemical and peroxide-driven oxidation of styrene with ultrathin polyion films containing P450cam and myoglobin. Chembiochem (2003) 4:82-89.
20. ESTAVILLO C, LU Z, JANSSON I, SCHENKMAN JB, RUSLING JF: Epoxidation of styrene by human cyt P450 1A2 by thin film electrolysis and peroxide activation compared to solution reactions. Biophys. Chem. (2003) 104:291-296.
21. FAULKNER KM, SHET MS, FISHER CW, ESTABROOK RW: Electrocatalytically driven ω-hydrdoxylation of fatty acids using cytochrome P450 4A1. Proc. Natl. Acad. Sci. USA (1995) 92:7705-7709.
22. ESTABROOK RW, FAULKNER KM, SHET MS, FISHER CW: Application of electrochemistry for P450-catalysed reactions. Methods Enzymol. (1996) 272:44-51.
23. UDIT AK, ARNOLD FH, GRAY HB: Cobaltocene-mediated catalytic monooxygenation using holo and heme domain cytochrome P450 BM3. J. Inorg. Biochem. (2004) 98:1547-1550.
24. IWUOHA EI, JOSEPH S, ZHANG Z et al.: Drug metabolism biosensors: electrochemical reactivities of cytochrome P450cam immobilised in synthetic vesicular systems. J. Pharm. Biomed. Anal. (1998) 17:1101-1110.
25. FANTUZZI A, FAIRHEAD M, GILARDI G: Direct electrochemistry of immobilized human cytochrome P450 2E1. J. Am. Chem. Soc. (2004) 126(16):5040-5041.
26. REIPA V, MAYHEW MP, VILKER VL: A direct electrode-driven P450 cycle for biocatalysis. Proc. Natl. Acad. Sci. USA (1997) 94:13554-13558.
27. SUGIHARAN, OGOMA Y, ABE K, KONDO Y, AKAIKE T: Immobilization of cytochrome P450 and electrochemical control of its activity. Polym. Adv. Technol. (1998) 9:307-313.
28. SHUMYANTSEVA VV, BULKO TV, BACHMANN TT et al.: Electrochemical reduction of flavocytochromes 2B4 and 1A2 and their catalytic activity. Arch. Biochem. Biophys. (2000) 377(1):43-48.
29. IWUOHA EI, WILSON A, HOWEL M et al.: Cytochrome P4502D6 (CYP2D6) bioelectrode for fluoxetine. Anal. Lett. (2004) 37(5):929-941.
30. SHUMYANTSEVA VV, IVANOV YD, BISTOLAS N et al.: Direct electron transfer of cytochrome P450 2B4 at electrodes modified with nonionic detergent and colloidal clay nanoparticles. Anal. Chem. (2004) 76(20):6046-6052.
31. JOSEPH S, RUSLING JF, LVOV YM, FRIEDBERG T, FUHR U: An amperometric biosensor with human CYP3A4 as a novel drug screening tool. Biochem. Pharmacol. (2003) 65:1817-1826.
32. PATERNOLLI C, ANTONINI M, GHISELLINI P, NICOLINI C: Recombinant cytochrome P450 immobilization for biosensor applications. Langmuir (2004) 20(26):11706-11712.
33. BARD AJ, FAULKNER LR: Electrochemical methods: Fundamentals and Applications. John Wiley & Sons, New York, USA (2001).
34. GUO L-H, HILL HAO: Direct electrochemistry of proteins and enzymes. Adv. Inorg. Chem. (1991) 36:341-375.
35. BOND AM: Chemical and electrochemical approaches to the investigation of redox reactions of simple electron transfer metalloproteins. Inorg. Chim. Acta. (1994) 226:293-340.
36. ARMSTRONG F, HILL HAO, WALTON NJ: Direct electrochemistry of redox proteins. Acc. Chem. Res. (1988) 21:407-413.
37. ARMSTRONG FA, WILSON GS: Recent developments in faradaic bioelectrochemistry. Electrochim. Acta (2000) 45:2623-2645.
38. RUSLING JF, ZHANG Z: Designing functional biomolecular films on electrodes. In: Biomolecular Films: Design, Function and Applications. JF Rusling (Ed.), Marcel Dekker Inc, New York, USA (2003): 1-64.
39. WU E-S, YANG CS: Lateral diffusion of cytochrome P450 in phospholipid bilayers. Biochemistry (1984) 23:28-33.
40. AGUEY-ZINSOU K-F, BERNHARDT PV, DE VOSS JJ, SLESSOR KE: Electrochemistry of P450cin: new insights into P450 electron transfer. Chem. Commun. (2003) 3:418-419.
41. KOO LS, IMMOS CE, COHEN MS, FARMER PJ, ORTIZ DE MONTELLANO PR: Enhanced electron transfer and lauric acid hydroxylation by site-directed mutagenesis of CYP119. J. Am. Chem. Soc. (2002) 124(20):5684-5691.
42. OKU Y, OHTAKI A, KAMITORI S et al.: Structure and direct electrochemistry of cytochrome P450 from the thermoacidophilic crenarchaeon, Sulfolobus tokodaii strain 7. J. Inorg. Biochem. (2004) 98:1194-1199.
43. SHUKLA A, GILLAM EM, MITCHELL DJ, BERNHARDT PV: Direct electrochemistry of enzymes from rhe cytochrome P450 2C family. Electrochem. Commun. (2005) 7:437-442.
44. JOHNSON DL, LEWIS BC, ELLIOT DJ, MINERS JO, MARTIN LL: Electrochemical characterisation of the human cytochrome CYP2C9. Biochem. Pharmacol. (2005) 69:1533-1541.
45. JOHNSON DL, CONLEY AJ, MARTIN LL: Direct electrochemistry of human, bovine and porcine cytochrome P450c17. J. Mol. Endocrinol. (2006) 36(2):349-359.
46. FISHER MT, SLIGAR SG: Control of heme protein redox potential and reduction rate: linear free energy relation between potential and ferric spin state equilibrium. J. Am. Chem. Soc. (1985) 107(17):5018-5019.
47. DAFF SN, CHAPMAN SK, TURNER KL et al.: Redox control of the catalytic cycle of flavocytochrome P450 BM3. Biochemistry (1997) 36(45):13816-13823.
48. LIGHT DR, ORME-JOHNSON NR: Beef adrenal cortical cytochrome P450 which catalyzes the conversion of cholesterol to pregnenolone. J. Biol. Chem. (1981) 256(1):343-350.
49. LAWSON RJ, LEYS D, SUTCLIFFE MJ et al.: Thermodynamic and biophysical characterization of cytochrome P450 Biol from Bacillus subtilis. Biochemistry (2004) 43(39):12410-12426.
50. KAZLAUSKAITE J, WESTLAKE ACG, WONG L-L, HILL HAO: Direct electrochemistry of cytochrome P450cam. Chem. Commun. (1996) 18:2189-2190.
51. TODOROVIC S, JUNG C, HILDEBRANDT P, MURGIDA DH: Conformational transitions and redox potential shifts of cytochrome P450 induced by immobilization. J. Biol. Inorg. Chem. (2006) 11:119-127.
52. JOHNSON DL, MARTIN LL: Controlling protein orientation at interfaces using histidine tags: an alternative to Ni/NTA. J. Am. Chem. Soc. (2005) 127(7):2018-2019.
53. SMITH DE: AC polaragraphy and related techniques: theory and practice. In: Electroanalytical Chemistry. AJ Bard (Ed.), Marcel Dekker, New York, USA (1966):1-155.
54. BOND AM, DUFFY NW, GUO S-X, ZHANG J, ELTON DM: Changing the look of voltammetry. Anal. Chem. (2005) 77(9):186A-196A.
55. ZHANG J, GUO S-X, BOND AM, MARKEN F: Large-amplitude Fourier transformed high-harmonic alternating current cyclic voltammetry: kinetic discrimination of interfering faradaic processes at glassy carbon and at boron-doped diamond electrodes. Anal. Chem. (2004) 76(13):3619-3629.
56. GUO S-X, ZHANG J, ELTON DM, BOND AM: Fourier transform large-amplitude alternating current cyclic voltammetry of surface-bound azurin. Anal. Chem. (2004) 76(1):166-177.
57. FLEMING BD, ZHANG J, BOND AM, BELL SG, WONG L-L: Separation of electron transfer and coupled chemical reaction components of biocatalytic processes using Fourier transform ac voltammetry. Anal. Chem. (2005) 77(11):3502-3510.
58. LEI C, WOLLENBERGER U, JUNG C, SCHELLER FW: Clay-bridged electron transfer between cytochrome P450cam and electrode. Biochem. Biophys. Res. Commun. (2000) 268(3):740-744.