Cytotoxicity of and DNA adduct formation by ellipticine in human U87MG glioblastoma cancer cells

Neuroendocrinology Letters

Volumn 30, Issue SUPPL.1, 2009, Pages 60-66

  Martinkova, Eva ^a,b   Dontenwill, Monique ^b   Frei, Eva ^c   Stiborova, Marie ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b Faculté de Pharmacie   (France)

^c GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

Anticancer drug; Cytochrome P450; DNA adduct; Ellipticine; Glioblastoma

Indexed keywords

12 HYDROXYELLIPTICINE; 13 HYDROXYELLIPTICINE; CYCLOOXYGENASE 1; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1B1; CYTOCHROME P450 3A4; DNA; DRUG METABOLITE; ELLIPTICINE; LACTOPEROXIDASE; PHOSPHORUS 32; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL PROLIFERATION; CONTROLLED STUDY; DNA ADDUCT; DNA MODIFICATION; DRUG CYTOTOXICITY; ENZYME ACTIVATION; GENE EXPRESSION; GLIOBLASTOMA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; POLYMERASE CHAIN REACTION; PROTEIN EXPRESSION; WESTERN BLOTTING;

EID: 77349123536     PISSN: 0172780X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Aimova D, Svobodova L, Kotrbova V, Mrazova B, Hodek P, Hudecek J, et al (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: 1926-1934.
2. Acton EM, Narayanan VL, Risbood PA, Shoemaker RH, Vistica DT, Boyd MR (1994). Anticancer specificity of some ellipticinium salts against human brain tumors in vitro. J Med Chem. 37: 2185-9.
3. Auclair C (1987). Multimodal action of antitumor agents on DNA: The ellipticine series. Arch Biochem Biophys. 259: 1-14.
4. Arguello F, Alexander MA, Greene JF Jr., Stinson SF, Jorden JL, Smith EM, et al (1998). Preclinical evaluation of 9-chloro-2-methylellipticinium acetate alone and in combination with conventional anticancer drugs for the treatment of human brain tumor xenografts. J Cancer Res Clin Oncol. 124: 19-26.
5. 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: 603-15.
6. Chen RM, Chou MW, Ueng TH (1998). Induction of cytochrome P450 1A in hamster liver and lung by 6-nitrochrysene. Arch Toxicol. 72: 395-401.
7. Chu Y, Hsu MT (1992). Ellipticine increases the superhelical density of intracellular SV40 DNA by intercalation. Nucleic Acids Res. 20: 4033-8.
8. Dickins M (2004). Induction of cytochromes P450. Curr Top Med Chem. 4: 1745-66.
9. Dutheil F, Dauchy S, Diry M, Sazdovitch V, Cloarec O, Mellottee L, et al (2009). Xenobiotic metabolizing enzymes and transporters in the normal human brain: regional and cellular mapping as a basis for putative roles in cerebral function. Drug Metab Dispos. 37:1528-38.
10. Dracinsky M, Sejbal J, Rygerova B, Stiborova M (2007). An efficient modification of ellipticine synthesis and preparation of 13-hydroxyellipticine. Tetrahetron Lett. 48: 6893-5.
11. Frei E, Bieler CA, Arlt VM, Wiessler M, Stiborova 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.
12. Froelich-Ammon SJ, Patchan MW, Osheroff N, Thompson RB (1995). Topoisomerase II binds to ellipticine in the absence or presence of DNA. Characterization of enzyme-drug interactions by fluorescence spectroscopy. J Biol Chem. 270: 14998-5004.
13. Garbett NC, Graves DE (2004). Extenting nature's leads: the anticancer agent ellipticine. Curr Med Chem Anti-Cancer Agents. 4: 149-72.
14. Iba MM, Fung J, Pak YM, Thomas PE, Fisher H, Sekowski A, et al (1999). Dose-dependent up-regulation of rat pulmonary, renal, and hepatic cytochrome P-450 (CYP) 1A expression by nicotine feeding. Drug Metab Dispos. 27: 977-82.
15. Iba MM, Fung J, Giannone JV, Okey AB (2000). Comparative induction of CYP1A1 expression by pyridine and its metabolites. Arch Biochem Biophys. 378: 299-310.
16. Krizkova J, Burdova K, Hudecek J, Stiborova M, Hodek P (2008). Induction of cytochromes P450 in small intestine by chemopreventive compounds. Neuroendocrinol. Lett. 29, 717-721.
17. 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.
18. 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: 789-95.
19. 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: 2550-7.
20. Livak KJ, Schmittgen TD (2001). Analysis of relative gene expression data using real-time quantitative PCR and the 2(-Delta Delta C(T)) Method. Methods. 25: 402-8.
21. Mondesir JM, Bidart JM, Goodman A, Alberici GF, Caille P, Troalen F, et al (1985). Drug-induced antibodies during 2-N-methyl-9-hydroxyellipticinium acetate (NSC-264137) treatment: schedule dependency and relationship to hemolysis. J Clin Oncol. 3: 735-40.
22. 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: 728-32.
23. Ohashi M, Sugikawa E, Nakanishi N (1995). Inhibition of p53 protein phosphorylation by 9-hydroxyellipticine: A possible anticancer mechanism. Jpn J Cancer Res. 86: 819-29.
24. Penas-Prado M, Gilbert MR (2007). Molecularly targeted therapies for malignant gliomas: advances and challenges. Expert Rev Anticancer Ther. 7:641-61.
25. 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: 1169-85.
26. 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: 270-9.
27. Poljakova J, Eckschlager T, Hrabeta J, Hrebickova 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: 1466-79.
28. Rouesse JG, Le Chevalier T, Caille P, Mondesir JM, Sancho-Garnier H, May-Levin F et al (1985). Phase II study of elliptinium in advanced breast cancer. CancerTreat Rep. 69: 707-8.
29. Sathornsumetee S, Reardon DA, Desjardins A, Quinn JA, Vredenburgh JJ, Rich JN (2007). Molecularly targeted therapy for malignant glioma. Cancer. 110: 13-24.
30. Shi LM, Fan Y, Myers TG, O'Connor PM, Pauli KD, Friend SH, et al (1998a). Mining the NCI anticancer drug discovery databases: genetic function approximation for the QSAR study of anticancer ellipticine analogues. J Chem Inf Comput Sci. 38: 189-99.
31. Shi LM, Myers TG, Fan Y, O'Connor PM, Pauli KD, Friend SH, et al (1998b). Mining the National Cancer Institute Anticancer Drug Discovery Database: cluster analysis of ellipticine analogs with p53-inverse and central nervous system-selective patterns of activity. Mol Pharmacol. 53: 241-51.
32. Somers R, Rouesse J, van Oosterom A, Thomas D (1985). Phase II study of elliptinium in metastatic soft tissue sarcoma. Eur J Cancer Clin Oncol. 21: 591-3.
33. 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: 1675-84.
34. 32P-postlabeling. Int J Cancer. 107: 885-90.
35. 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.
36. Stiborova M, Sejbal J, Borek-Dohalska L, Aimova D, Poljakova J, Forsterova K, 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: 8374-80.
37. Stiborova M, Rupertova M, Schmeiser HH, Frei E (2006). Molecular mechanism of antineoplastic action of an anticancer drug ellipticine. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 150: 13-23.
38. 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: 243-51.
39. 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.
40. 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: 318-27.
41. Sugikawa E, Hosoi T, Yazaki N, Gamanuma N, Nakanishi N, Ohashi M (1999). Mutant p53 mediated induction of cell cycle arrest and apoptosis at G1 phase by 9-hydroxyellipticine. Anticancer Res. 19: 3099-108.