DNA adduct formation by the anticancer drug ellipticine in rats determined by 32P postlabeling

International Journal of Cancer

Volumn 107, Issue 6, 2003, Pages 885-890

  Stiborová, Marie ^a   Breuer, Andrea ^b   Aimová, Dagmar ^a   Stibrová Rupertová, Martina ^a   Wiessler, Manfred ^b   Frei, Eva ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

32p postlabeling; Activation; Anticancer drug; Cytochrome P450; DNA adduct; Ellipticine

Indexed keywords

DEOXYGUANOSINE; DNA; ELLIPTICINE; PHOSPHORUS 32;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; CORRELATION ANALYSIS; COVALENT BOND; DNA ADDUCT; DNA DETERMINATION; DNA DRUG COMPLEX; DRUG ACTIVITY; DRUG DNA BINDING; DRUG MECHANISM; ENZYME ACTIVATION; HEART; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY; LIVER; LUNG; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN LOCALIZATION; RAT;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP1A2; DNA ADDUCTS; ELLIPTICINES; ISOTOPE LABELING; MALE; MICROSOMES; MICROSOMES, LIVER; ORGAN SPECIFICITY; PHOSPHORUS RADIOISOTOPES; RATS; RATS, WISTAR; TISSUE DISTRIBUTION;

EID: 0242425937     PISSN: 00207136     EISSN: None     Source Type: Journal    
DOI: 10.1002/ijc.11511     Document Type: Article

References (38)

1. Stiborová M, Bieler CA, Wiessler M, Frei E. The anticancer agent ellipticine on activation by cytochrome P450 forms covalent DNA adducts. Biochem Pharmacol 2001;62:1675-84.
2. Auclair C. Multimodal action of antitumor agents on DNA: the ellipticine series. Arch Biochem Biophys 1987;259:1-14.
3. Singh MP, Hill GC, Peoch D, Rayner B, Inabach JL, Lown JW. High-field NMR and restrained molecular modeling studies on a DNA heteroduplex containing a modified apurinic abasic site in the form of covalently linked 9-aminoellipticine. Biochemistry 1994;33:10271-85.
4. Chu Y, Hsu MT. Ellipticine increases the superhelical density of intracellular SV40 DNA by intercalation. Nucl Acids Res 1992;20:4033-8.
5. Monnot M, Mauffret O, Simon V, Lescot E, Psaume B, Saucier JM, Charra M, Belehradek J Jr, Fermandjian S. DNA-drug recognition and effects on topoisomerase II-mediated cytotoxicity: a three-mode binding model for ellipticine derivatives. J Biol Chem 1991;25:1820-9.
6. Fossé P, René B, Charra M, Paoletti C, Saucier JM. Stimulation of topoisomerase II-mediated DNA cleavage by ellipticine derivatives: structure-activity relationships. Mol Pharmacol 1992;42:590-5.
7. Froelich-Ammon SJ, Patchan MW, Osheroff N, Thompson RB. Topoisomerase II binds to ellipticine in the absence or presence of DNA: characterization of enzyme-drug interactions by fluorescence spectroscopy. J Biol Chem 1995;270:14998-5004.
8. Ohashi M, Sugikawa E, Nakanishi N. Inhibition of p53 protein phosphorylation by 9-hydroxyellipticine: a possible anticancer mechanism. Jpn J Cancer Res 1995;86:819-29.
9. Schwaller MA, Allard B, Lescot E, Moreau F. Protonophoric activity of ellipticine and isomers across the energy-transducing membrane of mitochondria. J Biol Chem 1995;270:22709-13.
10. Murray GI, Weaver RJ, Paterson PJ, Ewen SW, Melvin WT, Burke MD. Expression of xenobiotic metabolizing enzymes in breast cancer. J Pathol 1993;169:347-53.
11. Murray GI, Melvin WT, Burke M. Cytochrome P450 expression in tumors. J Pathol 1995;3:147-52.
12. Patterson LH, McKeown SR, Robson T, Gallagher R, Raleigh SM, Orr S. Antitumor prodrug development using cytochrome P450 (CYP) mediated activation. Anti-Cancer Drug Design 1999;14:473-86.
13. Stiborová M, Stiborová-Rupertová M, Bořek-Dohalská L, Wiessler M, Frei E. Rat microsomes activating the anticancer drug ellipticine to species covalently binding to deoxyguanosine in DNA are a suitable model mimicking elliptocine bioactivation in humans. Chem Res Toxicol 2003;16:38-47.
14. Frei E, Bieler CA, Arlt VM, Wiessler M, Stiborová M. Covalent binding of the anticancer drug ellipticine to DNA in V79 cells transfected with human cytochrome P450 enzymes. Biochem Pharmacol 2002;64:289-95.
15. Stiborová M, Martínek V, Rýdlová H, Hodek P, Frei E. Sudan 1 is a potential carcinogen for humans: evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes. Cancer Res 2002;62:5678-84.
16. Wiechelman KJ, Braun RD, Fitzpatrick JD. Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation. Anal Biochem 1988;175:231-7.
17. Omura T, Sato R. The carbon monoxide-binding pigment of liver microsomes: I, evidence for its hemoprotein nature. J Biol Chem 1964;239:2370-8.
18. Sottocasa GL, Kuylenstierna I, Ernster I, Bergstrand A. An electron transport system associated with the outer membrane of liver mitochondria. J Cell Biol 1967;32:415-38.
19. Vermilion JL, Coon MJ. Identification of the high and low potential flavins of liver microsomal NADPH-cytochrome P450 reductase. J Biol Chem 1978;253:8812-9.
20. Haugen DA, Coon MJ. Properties of electrophoretically homogeneous phenobarbital-inducible and beta-naphthoflavone-inducible forms of liver microsomal cytochrome P-450. J Biol Chem 1976;251:7929-39.
21. Yang CS, Tu YY, Koop DR, Coon MJ. Metabolism of nitrosamines by purified rabbit liver cytochrome P-450 isozymes. Cancer Res 1985;45:1140-5.
22. Saito T, Strobel HW. Purification to homogeneity and characterization of a form of cytochrome P-450 with high specificity for benzo[a]pyrene from β-naphthoflavone-pretreated rat liver microsomes. J Biol Chem 1981;256:984-8.
23. Yasukochi Y, Peterson JA, Masters B. NADPH-cytochrome c (P450) reductase: spectrophotometric and stopped flow kinetic studies on the formation of reduced flavoprotein intermediates. J Biol Chem 1979;254:7097-104.
24. Polson A, von Wechmar MB, van Regenmortel MH. Isolation of viral IgY antibodies from yolks of immunized hens. Immmunol Commun 1980;9:475-93.
25. Polson A, von Wechmar MB, Fazakerley G. Antibodies to proteins from yolk of immunized hens. Immmunol Commun 1980;9:494-514.
26. Laemmli UK. Cleavage of structural proteins during assembly of the head of bacteriophage T4. Nature 1970;227:680-5.
27. Murray BP, Edwards RJ, Murray S, Singleton AM, Davies DS, Boobis AR. Human hepatic CYP1A1 and CYP1A2 content, determined with specific anti-peptide antibodies, correlates with the mutagenic activation of PhIP. Carcinogenesis 1993;14:585-92.
28. Guengerich FP, Wang P, Davidson NK. Estimation of isozymes of microsomal cytochrome P-450 in rats, rabbits, ad humans using immunochemical staining coupled with sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Biochemistry 1982;21:1698-706.
29. Iba MM, Alam J, Touchard C, Thomas PE, Ghosal A, Fung J. Coordinate upregulation of CYP1A1 and HO-1 expression and modulation of δ-aminolevulinic acid synthase and tryptophan pyrrolase activities in pyridine-trated rats. Biochem Pharmacol 1999;58:723-34.
30. Sonner M, Crestiel T. Delayed ontogenesis of CYP1A2 in the human liver. Eur J Biochem 1998;251:893-8.
31. 32P-adduct assay comparative recoveries of structurally diverse DNA adducts in the various enhancement procedures. Carcinogenesis 1988;8:687-93.
32. 32P-postlabeling analysis using different chromatographic procedures. Carcinogenesis 1994;15:1187-92.
33. Stiborová M, Frei E, Sopko B, Wiessler M, Schmeiser HH. Carcinogenic aristolochic acids upon activation by DT-diaphorase form adducts found in DNA of patients with Chinese herbs nephropathy. Carcinogenesis 2002;23:617-25.
34. Nedelcheva V. Gut I P450 in the rat and man: methods of investigation, substrate specificities and relevance to cancer. Xenobiotica 1994;40:1151-75.
35. Aimová D, Dlouhá T, Frei E, Stiborová M. Anticancer drug ellipticine acts as an inducer of CYP1A1/2 and potentiates its own pharmacological efficiency. In: Anzenbacher P, Hudecek J, eds. Cytochromes P450, biochemistry, biophysics and drug metabolism: 13th International Conference on Cytochromes P450. Bologna, Italy: Monduzzi Editore, 2003. 133-8.
36. Frei E, Borek-Dohalská L, Wiessler M, Stiborová M. Ellipticine forms covalent DNA adducts in rats with properties similar to adducts formed in vitro after activation by cytochrome P450 or peroxidases. Proc Am Assoc Cancer Res 2001;42:252.
37. Aimová D, Stiborová M. Interaction of anticancer drug ellipticine with cytochromes P450 dictates its physiological properties. Chem Listy 2002;96:209.
38. DeMarini DM, Abu-Shakra A, Gupta R, Hendee LJ, Levine JG. Molecular analysis of mutations induced by the intercalating agent ellipticine at the hisD3052 allele of Salmonella typhimurium TA98. Environ Mol Mutagenesis 1992;20:12-8.