Open Access

Ellipticine and benzo(a)pyrene increase their own metabolic activation via modulation of expression and enzymatic activity of cytochromes P450 1A1 and 1A2


Cite

Aimová D, Svobodová L, Kotrbová V, Mrázová B, Hodek P, Hudecek J, Václavíková R, Frei E, Stiborová M (2007) The anticancer drug ellipticine is a potent inducer of rat cytochromes P450 1A1 and 1A2, thereby modulating its own metabolism. Drug Metab Dispos 35: 1926-34.10.1124/dmd.107.016048Search in Google Scholar

Arlt VM, Henderson CJ, Wolf CR, Schmeiser HH, Phillips DH, Stiborova M (2006) Bioactivation of 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone: evidence for DNA adduct formation mediated by cytochrome P450 enzymes and peroxidases. Cancer Lett 234: 220-31.10.1016/j.canlet.2005.03.035Search in Google Scholar

Arlt VM, Hewer A, Sorg BL, Schmeiser HH, Phillips DH, Stiborova M (2004) 3-Aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone, forms DNA adducts after metabolic activation by human and rat liver microsomes: evidence for activation by cytochrome P450 1A1 and P450 1A2. Chem Res Toxicol 17: 1092-101.10.1021/tx049912vSearch in Google Scholar

Arlt VM, Stiborova M, Henderson CJ, Osborne MR, Bieler CA, Frei E, Martinek V, Sopko B, Wolf CR, Schmeiser HH, Phillips DH (2005) Environmental pollutant and potent mutagen 3-nitrobenzanthrone forms DNA adducts after reduction by NAD(P)H: quinone oxidoreductase and conjugation by acetyltransferases and sulfotransferases in human hepatic cytosols. Cancer Res 65: 2644-52.10.1158/0008-5472.CAN-04-3544Search in Google Scholar

Arlt VM, Stiborová M, Henderson CJ, Thiemann M, Frei E, Aimová D, Singh R, Gamboa da Costa G, Schmitz OJ, Farmer PB, Wolf CR, Phillips DH (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: 656-65.Search in Google Scholar

Arlt VM, Stiborova M, Hewer A, Schmeiser HH, Phillips DH (2003) Human enzymes involved in the metabolic activation of the environmental contaminant 3-nitrobenzanthrone: evidence for reductive activation by human NADPH: cytochrome P450 reductase. Cancer Res 63: 2752-61.Search in Google Scholar

Baird WM, Hooven LA, Mahadevan B (2005) Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action. Environ Mol Mutagen 45: 106-14.10.1002/em.20095Search in Google Scholar

Bořek-Dohalská L, Frei E, Stiborová M (2004) DNA adduct formation by the anticancer drug ellipticine and its hydroxy derivatives in human breast adenocarcinoma MCF-7 cells. Collect Czech Chem Commun 69: 603-615.10.1135/cccc20040603Search in Google Scholar

Frei E, Bieler CA, Arlt VM, Wiessler M, Stiborová M (2002) Covalent binding of the anticancer drug ellipticine to DNA in V79 cells transfected with human cytochrome P450 enzymes. Biochem Pharmacol 64: 289-95.10.1016/S0006-2952(02)01072-9Search in Google Scholar

Henderson CJ, Otto DM, Carrie D, Magnuson MA, McLaren AW, Rosewell I, Wolf CR (2003) Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. J Biol Chem 278: 13480-6.10.1074/jbc.M21208720012566435Search in Google Scholar

Henderson CJ, Pass GJ, Wolf CR (2006) The hepatic cytochrome P450 reductase null mouse as a tool to identify a successful candidate entity. Toxicology letters 162: 111-7.10.1016/j.toxlet.2005.10.01616343823Search in Google Scholar

IARC Monogr Eval Carcinog Risk Chem Hum (1983) Polynuclear Aromatic Compounds 32, 211.Search in Google Scholar

Kotrbová V, Aimová D, Březinová A, Janouchová K, Poljaková J, Hodek P, Frei E, Stiborová M (2006) Cytochromes P450 reconstituted with NADPH: P450 reductase mimic the activating and detoxicating metabolism of the anticancer drug ellipticine in microsomes. Neuro Endocrinol Lett 27(Suppl. 2): 18-20.Search in Google Scholar

Kouri RE, Salerno RA, Whitmire CE (1973) Relationships between aryl hydrocarbon hydroxylase inducibility and sensitivity to chemically induced subcutaneous sarcomas in various strains of mice. J Natl Cancer Inst 50: 363-8.10.1093/jnci/50.2.3634702110Search in Google Scholar

Phillips DH (1999) Polycyclic aromatic hydrocarbons in the diet. Mutat Res 443: 139-47.10.1016/S1383-5742(99)00016-2Search in Google Scholar

Phillips DH (2002) Smoking-related DNA and protein adducts in human tissues Carcinogenesis 23: 1979-2004.10.1093/carcin/23.12.197912507921Search in Google Scholar

Poljaková J, Dračínský M, Frei E, Hudeček J Stiborová, M (2006) The effect of pH on peroxidase-mediated oxidation of and DNA-adduct formation by ellipticine. Collect. Czech. Chem. Commun. 71: 1169-1185.10.1135/cccc20061169Search in Google Scholar

Poljaková J, Frei E, Gomez JE, Aimová D, Eckschlager T, Hraběta J, Stiborová M (2007) DNA adduct formation by the anticancer drug ellipticine in human leukemia HL-60 and CCRF-CEM cells. Cancer Lett 252: 270-9.10.1016/j.canlet.2006.12.03717306925Search in Google Scholar

Stiborová M, Arlt VM, Henderson CJ, Wolf CR, Kotrbová V, Moserová M, Hudecek J, Phillips DH, Frei E. (2008) Role of hepatic cytochromes P450 in bioactivation of the anticancer drug ellipticine: studies with the hepatic NADPH: cytochrome P450 reductase null mouse. Toxicol Appl Pharmacol 226: 318-27.10.1016/j.taap.2007.09.01717976674Search in Google Scholar

Stiborová M, Bieler CA, Wiessler M, Frei E (2001) The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem Pharmacol 62: 675-84.10.1016/S0006-2952(01)00806-1Search in Google Scholar

Stiborová M, Bořek-Dohalská L, Aimová D, Kotrbová V, Kukačková K, Janouchová K, Rupertová M, Ryšlavá H, Hudeček J, Frei E (2006a) Oxidation pattern of the anticancer drug ellipticine by hepatic microsomes - Similarity between human and rat systems. Gen Physiol Biophys 25: 245-261.Search in Google Scholar

Stiborová M, Breuer A, Aimová D, Stiborová-Rupertová M, Wiessler M, Frei E (2003a) DNA adduct formation by the anticancer drug ellipticine in rats determined by 32P-postlabeling. Int J Cancer 107: 885-890.10.1002/ijc.1151114601046Search in Google Scholar

Stiborová M, Martínek V, Rýdlová 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: 145-154.10.1016/j.canlet.2004.07.03615766589Search in Google Scholar

Stiborová M, Poljaková J, Ryšlavá H, Dračínský M, Eckschlager T, Frei E (2007a) Mammalian peroxidases activate anticancer drug ellipticine to intermediates forming deoxyguanosine adducts in DNA identical to those found in vivo and generated from 12-hydroxyellipticine and 13-hydroxyellipticine. Int J Cancer 120: 243-251.10.1002/ijc.2224717066455Search in Google Scholar

Stiborová M, Rupertová M, Aimová D, Ryšlavá H, Frei E (2007b) Formation and persistence of DNA adducts of anticancer drug ellipticine in rats. Toxicology 236: 50-60.10.1016/j.tox.2007.03.02617482743Search in Google Scholar

Stiborová M, Rupertová M, Schmeiser HH, Frei E (2006b) Molecular mechanism of antineoplastic action of an anticancer drug ellipticine. Biomed Pap 150: 13-23.10.5507/bp.2006.00216936898Search in Google Scholar

Stiborová M, Sejbal J, Bořek-Dohalská L, Aimová D, Poljaková J, Forsterová K, Rupertová M, Wiesner J, Hudeček J, Wiessler M, Frei E (2004) The anticancer drug ellipticine forms covalent DNA adducts, mediated by human cytochromes P450, through metabolism to 13-hydroxyellipticine and ellipticine N2-oxide. Cancer Res 64: 8374-8380.10.1158/0008-5472.CAN-04-220215548707Search in Google Scholar

Stiborová M, Stiborová-Rupertová M, Bořek-Dohalská L, Wiessler M, Frei E (2003b) Rat microsomes activating the anticancer drug ellipticine to species covalently binding to deoxyguanosine in DNA are a suitable model mimicking ellipticine bioactivation in humans. Chem Res Toxicol 16: 38-47.10.1021/tx020081812693029Search in Google Scholar

Svobodová M Šístková J, Dračínská H, Hudeček J, Hodek P, Schmeiser HH, Arlt VM, Frei E, Stiborová M (2007) Reductive activation of environmental pollutants 3-nitrobenzanthrone and 2-nitrobenzanthrone. Che. Listy 100: s277-s279.Search in Google Scholar

Uno S, Dalton TP, Derkenne S, Curran CP, Miller ML, Shertzer HG, Nebert DW (2004) Oral exposure to benzo[a]pyrene in the mouse: detoxication by inducible cytochrome P450 is more important than metabolic activation. Mol Pharmacol 65: 1225-37.10.1124/mol.65.5.122515102951Search in Google Scholar

Uno S, Dalton TP, Dragin N, Curran CP, Derkenne S, Miller ML, Shertzer HG, Gonzalez FJ, Nebert DW (2006) Oral benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate. Mol Pharmacol 69: 1103-14.10.1124/mol.105.02150116377763Search in Google Scholar

eISSN:
1337-9569
ISSN:
1337-6853
Language:
English
Publication timeframe:
4 times per year
Journal Subjects:
Medicine, Clinical Medicine, Pharmacology, Toxicology