The stimulatory role of human cytochrome b5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: A new cell expression system to study cytochrome P450 mediated biotransformation

Mutagenesis

Volumn 20, Issue 2, 2005, Pages 93-100

  Duarte, Maria Paula ^a,b   Palma, Bernardo Brito ^a   Gilep, Andrei A ^c   Laires, António ^a,b   Oliveira, José Santos ^b   Usanov, Sergey A ^c   Rueff, José ^a   Kranendonk, Michel ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOPYRENE; 2 AMINO 3 METHYIMIDAZOL(4,5 F)QUINOLONE; 2 AMINOANTHRACENE; 4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; 6 CHRYSENAMINE; CHRYSENE DERIVATIVE; CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2A6; CYTOCHROME P450 2E1; DIPROPYLNITROSAMINE; PYRENE DERIVATIVE; QUINOLONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE FERRIHEMOPROTEIN REDUCTASE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHEMICAL MUTAGENESIS; CONTROLLED STUDY; ESCHERICHIA COLI K 12; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ARYL HYDROCARBON HYDROXYLASES; BIOTRANSFORMATION; CARCINOGENS; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 CYP2E1; CYTOCHROMES B5; ENZYME ACTIVATION; ESCHERICHIA COLI K12; HUMANS; MIXED FUNCTION OXYGENASES; MUTAGENICITY TESTS; MUTAGENS; NADPH-FERRIHEMOPROTEIN REDUCTASE; PLASMIDS; RECOMBINANT PROTEINS; XENOBIOTICS;

ESCHERICHIA; ESCHERICHIA COLI K12;

EID: 18344393458     PISSN: 02678357     EISSN: None     Source Type: Journal    
DOI: 10.1093/mutage/gei012     Document Type: Article

References (31)

1. Henderson,C.J., Otto,D.M.E., Carrie,D., Magnuson,M.A., McLaren,A.W., Rosewell,A.W. and Wolf,C.R. (2003) Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. J. Bio. Chem., 278, 13480-13486.
2. Ingelman-Sundberg,M. (2004) Human drug metabolising cytochrome P450 enzymes: properties and polymorphisms. Nanuyn-Schmiedebergs Arch. Pharmacol., 369, 89-104.
3. Ingelman-Sundberg,M. (2001) Genetic susceptibility to adverse effects of drugs and environmental toxicants. The role of the CYP family of enzymes. Mutat. Res., 482, 11-19.
4. Autrup,H. (2000) Genetic polymorphisms in human xenobiotica metabolizing enzymes as susceptibility factors in toxic response. Mutat. Res., 464, 65-76.
5. Guengerich,F.P. (1998) The environmental genome project: functional analysis of polymorphisms. Environ. Health Perspect., 106, 365-368.
6. Kranendonk,M., Laires,A., Rueff,J., Estabrook,R.W. and Vermeulen,N.P.E. (2000) Heterologous expression of xenobiotic mammalian-metabolizing enzymes in mutagenicity tester bacteria: an update and practical considerations. CRC Crit. Rev. Toxicol., 30, 287-306.
7. Rueff,J., Gaspar,J. and Kranendonk,M. (2002) DNA polymorphisms as modulators of genotoxicity and cancer. Biol. Chem., 383, 923-932.
8. Kranendonk,M., Fisher,C.W., Roda,R., Carreira,F., Theisen,P., Laires,A., Rueff,J., Vermeulen,N.P.E. and Estabrook,R.W. (1999) Escherichia coli MTC, a NADPH cytochrome P450 reductase competent mutagenicity tester strain for the expression of human cytochrome P450: comparison of three types of expression systems. Mutat. Res., 439, 287-300
9. Kranendonk,M., Roda,R., Carreira,F., Theisen,P., Laires,A., Fisher,C.W., Rueff,J., Vermeulen,N.P.E. and Estabrook,R.W. (1999). Escherichia coli MTC, a human NADPH cytochrome P450 reductase competent mutagenicity tester strain for the expression of human cytochrome P450 isoforms 1A1, 1A2, 2A6, 3A4 or 3A5: catalytic activities and mutagenicity studies. Mutat. Res., 441, 73-83.
10. Schenkan,J.B. and Jansson,I. (2003) The many roles of cytochrome b5. Pharmacol. Ther., 97, 139-152.
11. Yamaori,S., Yamazaki,H., Suzuki,A., Yamada,A., Tani,H., Kamidate,T., Fujita,K. and Kamataki,T. (2003) Effects of cytochrome b5 on drug oxidation activities of human cytochrome P450 (CYP) 3As: similarity of CYP3A5 with CYP3A4 but not CYP3A7. Biochem. Pharmacol., 66, 2333-2340.
12. Voice,M.W., Zhang,Y., Wolf,R., Burchel,B. and Friedberg,T. (1999) Effects of human cytochrome b5 on CYP3A4 activity and stability in vivo. Arch. Biochem. Biophys., 366, 116-124.
13. Yamazaki,H., Gillam,E.M.J., Dong,M.S., Johnson,W.W., Guengerich,F.P. and Shimada,T. (1997) Reconstitution of recombinant cytochrome P450 2C10(2C9) and comparison with cytochrome 3A4 and other forms: Effect of cytochrome P450-P450 and cytochrome P450-b5 interactions. Arch. Biochem. Biophys., 342, 329-337.
14. Yamazaki,H., Nakamura,M., Komatsu,T., Ohyama,K., Hatanaka,N., Asahi,S., Shimada,N., Guengerich,F.P., Shimada,T., Nakajima,M. and Yokoi,T. (2002) Roles of NADPH-P450 reductase and apo- and holocytochrome b5 on xenobiotic oxidations catalysed by 12 recombinant human cytochrome P450s expressed in membranes of Escherichi coli. Protein Expr. Purif., 24, 329-337.
15. Cooper,M.T. and Porter,T.D. (2001) Cytochrome b5 coexpression increases the CYP2E1-dependent mutagenicity of dialkylnitrosamines in methyltransferase- dencient strains of Salmonella typhimurium. Mutat. Res., 484, 61-68.
16. Mokashi,V., Li,L. and Porter,T.D. (2003) Cytochrome b5 reductase and cytochrome b5 support the CYP2E1-mediated activation of nitrosamines in a recombinant Ames test. Mutat. Res., 412, 147-152.
17. Yamazaki,H., Nakano,M., Gillam,E.M.J., Bell,L.C., Guengerich,F.P. and Shimada,T. (1996) Requirement for cytochrome b5 in the oxidation of 7-ethoxycoumarin, chlorzoxazone, aniline, and N-nitrosodimethylamine by recombinant cytochrome P450 2E1 and by human liver microsomes. Biochem. Pharmacol., 52, 301-309.
18. Loughran,P.A., Roman,L.J., Miller,R.T. and Masters,B.S.S. (2001) The kinetic and spectral characterization of the E.coli expressed mammalian CYP4A7: cytochrome b5 effects vary with substrate. Arch. Biochem. Biophys., 385, 311-321.
19. Kang,I.H., Kim,H.J., Oh,H., Park,Y.I. and Dong,M.S. (2004). Biphasic effects of the flavonoids quercetin and naringenin on the metabolic activation of 2-amino-3,5-dimethylimidazo[4,5-f]quinoline by Salmonella typhimurium TA1538 co-expressing human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and cytochrome b5. Mutat. Res., 545, 37-47.
20. Gilep,A.A., Guryev,O.L., Usanov,S.A. and Estabrook,R.W. (2001) Expression, purification, and physical properties of recombinant flavocytochrome fusion proteins containing rat cytochrome b5 linked to the NADPH-cytochrome P450 reductase by different membrane-binding segments. Arch. Biochem. Biophys., 2, 222-234.
21. Yamazaki,H., Shimada,T., Martin,M.V. and Guengerich,F.P. (2001) Stimulation of cytochrome P450 reactions by apo-cytochrome b5. J. Biol. Chem., 276, 30885-30891
22. Holmans,P.L., Shet,M.S., Martin-Wixtrom,C.A., Fisher,C.W. and Estabrook,R.W. (1994) The high-level expression in Escherichia coli of the membrane-bound form of rat cytochrome b5 and studies on their mechanism of function. Arch. Biochem. Biophys., 2, 554-565.
23. Kranendonk,M., Pintado,F., Mesquita,P., Laires,A., Vermeulen,N.P.E. and Rueff,J. (1996) MX100, a new Escherichia coli tester strain for use in genotoxicity studies. Mutagenesis, 11, 327-333.
24. Sambrook,J., Fritsch,T.F. and Maniatis,T. (1989). Molecular Cloning: A Laboratory Manual, 2nd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
25. Kranendonk,.M, Mesquita,P., Laires,A., Vermeulen,N.P.E. and Rueff,J. (1998) Expression of human cytochrome P450 1A2 in Escherichia coli: a system for biotransformation and genotoxicity studies of chemical carcinogens. Mutagenesis, 13, 263-269.
26. Pearce,R.R., McIntyre,C.J., Madan,A., Sanzgiri,U., Draper,A.J., Bullock,P.L., Cook,D.C., Burton,A., Latham,J., Nevins,C. and Parkinson,A. (1996) Effects of freezing, thawing and storing human liver microsomes on cytochrome P450 activity. Arch. Biochem. Biophys., 2, 145-169.
27. Kranendonk,M., Commandeur,J.N., Laires,A., Rueff,J. and Vermeulen,N.P.E. (1997) Characterization of enzyme activities and cofactors involved in bioactivation and bioinactivation of chemical carcinogens in the tester strains Escherichia coli K12 MX100 and Salmonella typhimurium LT2 TA100. Mutagenesis, 12, 245-254.
28. Paine,M.F., Khalighi,M., Fisher,J.M., Shen,D.D., Kunze,K.L., Marsh,C.L., Perkins,J.D. and Thummel,K.E. (1997) Characterization of interintestinal and intraintestinal variations in human CYP3A4-dependent metabolism. J. Pharmacol. Exp. Ther., 283, 1552-1562.
29. Yamazaki,H., Nakajima,M., Nakamura,M., Asahi,S., Shimada,N., Gillam,E.M.J., Guengerich,F.P., Shimada,T. and Yokoi,T. (1999) Enhancement of cytochrome P-450 3A4 catalytic activities by cytochrome b5 in bacterial membranes. Drug Metab. Dispos., 27, 999-1004.
30. Venkatakrishnan,K., Von Moltke,L.L., Court,J.S., Harmatz,J.S., Crespi,C.L. and Greenblatt,D.J. (2000) Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between approaches. Drug Metab. Dispos., 28, 1493-1504.
31. Fisher,C.W., Caudle,D.L., Martin-Wixtrom,C., Quattrochi,L.C., Tukey,R.H., Waterman,M.R. and Estabrook,R.W. (1992) High-level expression of functional human cytochrome P450 1A2 in Escherichia coli. FASEB J., 6, 759-764.