The effect of benzo[a]pyrene on metabolic activation of anticancer drug ellipticine in mice

Neuroendocrinology Letters

Volumn 34, Issue SUPPL. 2, 2013, Pages 43-54

  Stiborova, Marie ^a   Cerna, Vera ^a   Moserova, Michaela ^a   Arlt, Volker M ^b   Frei, Eva ^c  

^a CHARLES UNIVERSITY   (Czech Republic)

^b KING'S COLLEGE LONDON   (United Kingdom)

^c GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

Anticancer drug; Benzo a pyrene; Cytochrome P450 1A1 2; DNA adducts; Ellipticine; Induction

Indexed keywords

BENZO[A]PYRENE; CYTOCHROME B5; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; ELLIPTICINE; PEROXIDASE; PHOSPHORUS 32; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DRUG METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZO(A)PYRENE; BIOTRANSFORMATION; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; CYTOCHROME P-450 ENZYME SYSTEM; DRUG EVALUATION, PRECLINICAL; DRUG INTERACTIONS; ELLIPTICINES; FEMALE; MICE; MICE, INBRED C57BL; MICE, TRANSGENIC; MICROSOMES, LIVER;

EID: 84893946056     PISSN: 0172780X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (55)

1. 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: 2752-2761. (Pubitemid 36667145)
2. 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: 1092-1101. (Pubitemid 39108677)
3. 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: 220-231.
4. Arlt VM, Stiborova M, Henderson CJ, Thiemann M, Frei E, Aimova D, 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. (Pubitemid 351404884)
5. 32P-postlabelling. Toxicol Lett. 213: 160-166.
6. Auclair C (1987). Multimodal action of antitumor agents on DNA: The ellipticine series. Arch Biochem Biophys. 259: 1-14.
7. Borek-Dohalska L, Frei E, Stiborova 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 (Pubitemid 38526511)
8. Bui PH and Hankinson O (2009a). Functional characterization of human cytochrome P450 2S1 using a synthetic gene-expressed protein in Escherichia coli. Mol Pharmacol. 76: 1031-1043.
9. Bui PH, Hsu EL, Hankinson O (2009b). Fatty acid hydroperoxides support cytochrome P450 2S1-mediated bioactivation of benzo[a]pyrene-7,8-dihydrodiol. Mol Pharmacol. 76: 1044-1052.
10. Downie D, McFadyen MC, Rooney PH, Cruickshank ME, Parkin DE, Miller ID, et al (2005). Profiling cytochrome P450 expression in ovarian cancer: identification of prognostic markers. Clin Cancer Res. 11: 7369-7735.
11. Eling TE, Thompson DC, Foureman GL, Curtis JF, Hughes MF (1990). Prostaglandin H synthase and xenobiotic oxidation. Annu Rev Pharmacol Toxicol. 30: 1-45.
12. Eling TE and Curtis JF (1992). Xenobiotic metabolism by prostaglandin H synthase. Pharm Ther. 53: 261-273.
13. Garbett NC and Graves DE (2004). Extenting nature's leads: the anticancer agent ellipticine. Curr Med Chem Anti-Cancer Agents. 4: 149-172. (Pubitemid 38404690)
14. Henderson CJ, Otto DME, Carrie D, Magnuson MA, McLaren AW, Rosewell I, et al (2003). Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. J Biol Chem. 278: 13480-13486. (Pubitemid 36800122)
15. Hodek P, Krizkova J, Frei E, Singh R, Arlt VM, Stiborova M (2011). Impact of beta-naphthoflavone on genotoxicity of food-derived carcinogens. Neuroendocrinol Lett. 32: 25-34.
16. Hodek P, Trefil P, Simunek J, Hudecek J, Stiborova M (2013). Optimized protocol of chicken antibody (IgY) purification providing electrophoretically homogenous preparations. Int J Electrochem Sci. 8: 113-124.
17. Kizek R, Adam V, Hrabeta J, Eckschlager T, Smutny S, Burda JV, et al (2012). Anthracyclines and ellipticines as DNA-damaging anticancer drugs; recent advances. Pharmacol Ther. 133: 26-39.
18. Kotrbova V, Aimova D, Brezinova A, Janouchova K, Poljakova J, Hodek P, et al (2006). Cytochromes P450 reconstituted with NADPH:P450 reductase mimic the activating and detoxicating metabolism of the anticancer drug ellipticine in microsomes. Neuroendocrinol Lett. 27: 18-20. (Pubitemid 46534329)
19. 5 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.
20. Kuo PL, Hsu YL, Chang CH, Lin CC (2005a). The mechanism of ellipticine-induced apoptosis and cell cycle arrest in human breast MCF-7 cancer cells. Cancer Lett. 223: 293-301. (Pubitemid 40719627)
21. Kuo PL, Hsu YL, Kuo YC, Chang CH, Lin CC (2005b). The antiproliferative inhibition of ellipticine in human breast mda-mb-231 cancer cells is through cell cycle arrest and apoptosis induction. Anti-Cancer Drugs. 16: 789-795. (Pubitemid 41104930)
22. Kuo PL, Kuo YC, Hsu YL, Cho CY, Lin CC (2006). Ellipticine induced apoptosis through p53-dependent pathway in human hepatocellular carcinoma HepG2 cells. Life Sci. 78: 2550-2557.
23. Lu H, Chen CS, Waxman DJ (2009). Potentiation of methoxymorpholinyl doxorubicin antitumor activity by P450 3A4 gene transfer. Cancer Gene Ther. 16: 393-404.
24. Ma J and Waxman DJ (2007). Collaboration between hepatic and intratumoral prodrug activation in a P450 prodrug-activation gene therapy model for cancer treatment. Mol Cancer Ther. 6: 2879-2890. (Pubitemid 350206766)
25. Martinkova E, Dontenwill M, Frei E, Stiborova M (2009). Cytotoxicity of and DNA adduct formation by ellipticine in human U87MG glioblastoma cancer cells. Neuroendocrinol Lett. 30: 60-66.
26. Martinkova E, Maglott A, Leger, DY, Bonnet D, Stiborova M, Takeda K, et al (2010). α5β1 integrin antagonists reduce chemotherapy-induced premature senescence and facilitate apoptosis in human glioblastoma cells. Int J Cancer. 127: 1240-1248.
27. Moserova M, Kotrbova V, Rupertova M, Naiman K, Hudecek J, Hodek P, et al (2008). Isolation and partial characterization of the adduct formed by 13-hydroxyellipticine with deoxyguanosine in DNA. Neuroendocrinol Lett. 29: 728-732.
28. Phillips DH and Venitt S (2012). DNA and protein adducts in human tissues resulting from exposure to tobacco smoke. Int J Cancer. 131: 2733-2753.
29. Poljakova J, Dracinsky M, Frei E., Hudecek J, Stiborova M (2006). The effect of pH on peroxidase-mediated oxidation of and DNA-adduct formation by ellipticine. Collect Czech Chem Commun. 71: 1169-1185. (Pubitemid 44432311)
30. Poljakova J, Frei E, Gomez JE, Aimova D, Eckschlager T, Hrabeta J, et al (2007). DNA adduct formation by the anticancer drug ellipticine in human leukemia HL-60 and CCRF-CEM cells. Cancer Lett. 252: 270-279. (Pubitemid 46809792)
31. Poljakova J, Eckschlager T, Hrabeta J, Hrebackova J, Smutny S, Frei E, et al (2009). The mechanism of cytotoxicity and DNA adduct formation by the anticancer drug ellipticine in human neuroblastoma cells. Biochem Pharmacol. 77: 1466-1479.
32. Poljakova J, Hrebackova J, Dvorakova M, Moserova M, Eckschlager T, Hrabeta J, et al (2011). Anticancer agent ellipticine combined with histone deacetylase inhibitors, valproic acid and trichostatin A, is an effective DNA damage strategy in human neuroblastoma. Neuroendocrinol Lett. 32: 101-116.
33. Poljakova J, Eckschlager T, Kizek R, Frei E, Stiborova M (2013). Electrochemical determination of enzymes metabolizing ellipticine in thyroid cancer cells - a tool to explain the mechanism of ellipticine toxicity to these cells. Int J Electrochem Sci. 8: 1573-1585.
34. Rendic S and DiCarlo FJ (1997). Human cytochrome P450 enzymes: A status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev. 29: 413-480.
35. Saarikoski T, Rivera SP, Hankinson O, Husgafvel-Pursiainen K (2005). CYP2S1: a short review. Toxicol Appl Pharmacol. 207: 62-69.
36. Slepneva IA, Sergeeva SV, Khramtsov W (1995). Reversible inhibition of NADPH-cytochrome P450 reductase by alpha-lipoic acid. Biochem Biophys Res Commun. 214: 1246-1253.
37. Stiborova M, Bieler CA, Wiessler M, Frei E (2001). The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem Pharmacol. 62: 675-684.
38. 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. (Pubitemid 35204721)
39. Stiborova M, Breuer A, Aimova D, Stiborova-Rupertova 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. (Pubitemid 37429828)
40. Stiborova M, Stiborova-Rupertova M, Borek-Dohalska 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. (Pubitemid 36139409)
41. Stiborova M, Sejbal J, Borek-Dohalska L, Poljakova J, Forsterova K, Rupertova M, et al (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. (Pubitemid 39496831)
42. Stiborova M, Frei E, Hodek P, Wiessler M, Schmeiser HH (2005). Human hepatic and renal microsomes, cytochromes P450 1A1/2, NADPH:cytochrome P450 reductase and prostaglandin H synthase mediate the formation of aristolochic acid-DNA adducts found in patients with urothelial cancer. Int J Cancer. 113: 189-197. (Pubitemid 39628308)
43. Stiborova M, Borek-Dohalska L, Kotrbova V, Kukackova K, Janouchova K, Rupertova M, et al (2006a). Oxidation pattern of the anticancer drug ellipticine by hepatic microsomes - Similarity between human and rat systems. Gen Physiol Biophys. 25: 245-261. (Pubitemid 44857439)
44. Stiborova M, Dracinska H, Hajkova J, Kaderabkova P, Frei E, Schmeiser HH, et al (2006b). The environmental pollutant and carcinogen 3-nitrobenzanthrone and its human metabolite 3-aminobenzanthrone are potent inducers of rat hepatic cytochromes P450 1A1 and -1A2 and NAD(P)H:quinone oxidoreductase. Drug Metab Dispos. 34: 1398-1405. (Pubitemid 44079882)
45. Stiborova M, Rupertova M, Schmeiser HH, Frei E (2006c). Molecular mechanism of antineoplastic action of an anticancer drug ellipticine. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 150: 13-23.
46. Stiborova M, Poljakova J, Ryslava H, Dracinsky 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. (Pubitemid 44956832)
47. Stiborova M, Rupertova M, Aimova D, Ryslava H, Frei E (2007b). Formation and persistence of DNA adducts of anticancer drug ellipticine in rats. Toxicology. 236: 50-60. (Pubitemid 46777068)
48. Stiborova M, Arlt VM, Henderson CJ, Wolf CR, Kotrbova V, Moserova M, et al (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: 318-327. (Pubitemid 351172414)
49. Stiborova M, Moserova M., Mrazova B, Kotrbova V, Frei E (2010). Role of cytochromes P450 and peroxidases in metabolism of the anticancer drug ellipticine: additional evidence of their contribution to ellipticine activation in rat liver, lung and kidney. Neuroendocrinol Lett. 31: 26-35.
50. Stiborova M, Rupertova M, Frei E (2011). Cytochrome P450- and peroxidase-mediated oxidation of anticancer alkaloid ellipticine dictates its anti-tumor efficiency. Biochim Biophys Acta. 1814: 175-185.
51. Stiborova M, Cechova T, Borek-Dohalska L, Moserova M, Frei E, Schmeiser HH, et al (2012a). Activation and detoxification metabolism of urban air pollutants 2-nitrobenzanthrone and carcinogenic 3-nitrobenzanthrone by rat and mouse hepatic microsomes. Neuroendocrinol Lett. 33: 8-15.
52. 5 increases cytochrome P450 3A4-mediated activation of anticancer drug ellipticine to 13-hydroxyellipticine whose covalent binding to DNA is elevated by sulfotransferases and N,O-acetyltransferases. Chem Res Toxicol. 25: 1075-1085.
53. 32P-postlabeling technique. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 156: 115-121.
54. 5. Toxicology. 302: 233-241.
55. Ueng Y-F, Kuwabara T, Chun Y-J, Guengerich FP (1997). Cooperativity in oxidation catalyzed by cytochrome P450 3A4. Biochemistry. 36: 370-381. (Pubitemid 27043473)