The impact of individual cytochrome P450 enzymes on oxidative metabolism of benzo[a]pyrene in human livers

Environmental and Molecular Mutagenesis

Volumn 57, Issue 3, 2016, Pages 229-235

  Šulc, Miroslav ^a   Indra, Radek ^a   Moserová, Michaela ^a   Schmeiser, Heinz H ^b   Frei, Eva ^a   Arlt, Volker M ^c,d   Stiborová, Marie ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^c KING'S COLLEGE LONDON   (United Kingdom)

^d PUBLIC HEALTH ENGLAND   (United Kingdom)

Author keywords

Benzo a pyrene; Cytochrome P450; Human liver; Metabolism

Indexed keywords

BENZO[A]PYRENE; CYTOCHROME B5; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; CYTOCHROME P450 2A6; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; BENZO(A)PYRENE-DNA ADDUCT; DNA ADDUCT;

AEROBIC METABOLISM; ARTICLE; DETOXIFICATION; DNA ADDUCT; ENZYME ACTIVATION; HUMAN; HUMAN TISSUE; LIVER; OXIDATION; PROTEIN EXPRESSION; ANIMAL; DRUG INACTIVATION; ENZYMOLOGY; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; METABOLISM; OXIDATION REDUCTION REACTION; RABBITS AND HARES;

ANIMALS; BENZO(A)PYRENE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DNA ADDUCTS; HUMANS; INACTIVATION, METABOLIC; LIVER; MICROSOMES, LIVER; OXIDATION-REDUCTION; RABBITS;

EID: 84960443957     PISSN: 08936692     EISSN: 10982280     Source Type: Journal    
DOI: 10.1002/em.22001     Document Type: Article

References (25)

1. Arlt VM, Stiborova M, Henderson CJ, Thiemann M, Frei E, Aimova D, Singhs R, da Costa GG, Schmitz OJ, Farmer PB, et al. 2008. Metabolic activation of benzo[a]pyrene in vitro by hepatic cytochrome P450 contrasts with detoxification in vivo: experiments with hepatic cytochrome P450 reductase null mice. Carcinogenesis 29:656-665.
2. Arlt VM, Krais AM, Godschalk RW, Riffo-Vasquez Y, Mrizova I, Roufosse CA, Corbin C, Shi Q, Frei E, Stiborova M, et al. 2015. Pulmonary inflammation impacts on CYP1A1-mediated respiratory tract DNA damage induced by the carcinogenic air pollutant benzo[a]pyrene. Toxicol Sci 146:213-225.
3. Baird WM, Hooven LA, Mahadevan B. 2005. Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action. Environ Mol Mutagen 45:106-114.
4. Bauer E, Guo Z, Ueng YF, Bell LC, Zeldin D, Guengerich FP. 1995. Oxidation of benzo[a]pyrene by recombinant human cytochrome P450 enzymes. Chem Res Toxicol 8:136-142.
5. Edwards RJ, Adams DA, Watts PS, Davies DS, Boobis AR. 1998. Development of a comprehensive panel of antibodies against the major xenobiotic metabolising forms of cytochrome P450 in humans. Biochem Pharmacol 56:377-387.
6. Endo K, Uno S, Seki T, Ariga T, Kusumi Y, Mitsumata M, Yamada S, Makishima M. 2008. Inhibition of aryl hydrocarbon receptor transactivation and DNA adduct formation by CYP1 isoform-selective metabolic deactivation of benzo[a]pyrene. Toxicol Appl Pharmacol 230:135-143.
7. Estrada DF, Skinner AL, Laurence JS, Scott EE. 2014. Human cytochrome P450 17A1 conformational celection. J Biol Chem 289:14310-14320.
8. 5 by NADPH-cytochrome P450 reductase. Arch Biochem Biophys 440:204-211.
9. 5 reductase can act as sole electron donors to the hepatic cytochrome P450 system. Mol Pharmacol 83:1209-1217.
10. Huang MT, Wood AW, Chang RL, Yagi H, Sayer JM, Jerina DM, Conney AH. 1986. Inhibitory effect of 3-hydroxybenzo(a)pyrene on the mutagenicity and tumorigenicity of (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7, 8, 9, 10-tetrahydrobenzo(a)pyrene. Cancer Res 46:558-566.
11. Iarc 2010. International Agency for Research on Cancer. Some non-heterocyclic polycyclic aromatic hydrocarbons and some related exposures. IARC Monogr Eval Carcinog Risks Hum 92:1-853.
12. Indra R, Moserova M, Kroftova N, Sulc M, Martinkova M, Adam V, Eckschlager T, Kizek R, Arlt VM, Stiborova M. 2014. Modulation of human cytochrome P450 1A1-mediated oxidation of benzo[a]pyrene by NADPH:cytochrome P450 oxidoreductase and cytochrome b5. Neuro Endocrinol Lett 35:105-113.
13. Jiang H, Gelhaus SL, Mangal D, Harvey RG, Blair IA, Penning TM. 2007. Metabolism of benzo[a]pyrene in human bronchoalveolar H358 cells using liquid chromatography-mass spectrometry. Chem Res Toxicol 20:1331-1341.
14. Kim JH, Stansbury KH, Walker NJ, Trush MA, Strickland PT, Sutter TR. 1998. Metabolism of benzo[a]pyrene and benzo[a]pyrene-7, 8-diol by human cytochrome P450 1B1. Carcinogenesis 19:1847-1853.
15. Kucab JE, van Steeg H, Luijten M, Schmeiser HH, White PA, Phillips DH, Arlt VM. 2015. TP53 mutations induced by BPDE in Xpa-WT and Xpa-Null human TP53 knock-in (Hupki) mouse embryo fibroblasts. Mutat Res 773:48-62.
16. Kotrbova V, Mrazova B, Moserova M, Martinek V, Hodek P, Hudecek J, Frei E, Stiborova M. 2011. Cytochrome b5 shifts oxidation of the anticancer drug ellipticine by cytochromes P450 1A1 and 1A2 from its detoxication to activation, thereby modulating its pharmacological efficacy. Biochem Pharmacol 82:669-680.
17. 5 profoundly affects hepatic and extrahepatic drug metabolism. Mol Pharmacol 75:269-278.
18. 5 in cytochrome P450 reactions. J Biochem Mol Toxicol 16:311-316.
19. Rendic S, Di Carlo FJ. 1997. Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 29:413-580.
20. Schenkman JB, Jansson I. 2003. The many roles of cytochrome b5. Pharmacol Ther 97:139-152.
21. Shi Q, Haenen GR, Maas L, Arlt VM, Spina D, Vasquez YR, Moonen E, Veith C, Van Schooten FJ, Godschalk RW. Inflammation-associated extracellular β-glucuronidase alters cellular responses to the chemical carcinogen benzo[a]pyrene. Arch Toxicol (in press). doi: 10.1007/s00204-015-1593-7.
22. Stiborova M, Martinek V, Rydlova H, Hodek P, Frei E. 2002. Sudan I is a potential carcinogen for humans: Evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes. Cancer Res 62:5678-5684.
23. Stiborova M, Martinek V, Rydlova H, Koblas T, Hodek P. 2005. Expression of cytochrome P450 1A1 and its contribution to oxidation of a potential human carcinogen 1-phenylazo-2-naphthol (Sudan I) in human livers. Cancer Lett 220:145-154.
24. Stiborova M, Martinek V, Schmeiser HH, Frei E. 2006. Modulation of CYP1A1-mediated oxidation of carcinogenic azo dye Sudan I and its binding to DNA by cytochrome b5. Neurol Endocrinol Lett 27(Suppl2):35-39.
25. Stiborova M, Moserova M, Cerna V, Indra R, Dracinsky M, Šulc M, Henderson CJ, Wolf CR, Schmeiser HH, Phillips DH, Frei E, Arlt VM. 2014. Cytochrome b5 and epoxide hydrolase contribute to benzo[a]pyrene-DNA adduct formation catalyzed by cytochrome P450 1A1 under low NADPH:P450 oxidoreductase conditions. Toxicology 318:1-12.