Comparison of DNA adduct formation by aristolochic acids in various in vitro activation systems by 32P-post-labelling: Evidence for reductive activation by peroxidases

Carcinogenesis

Volumn 18, Issue 5, 1997, Pages 1055-1062

  Schmeiser, Heinz H ^a   Frei, Eva ^a   Wiessler, Manfred ^a   Stiborová, Marie ^b  

^a GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ARISTOLOCHIC ACID; CARCINOGEN; DNA; HORSERADISH PEROXIDASE; LACTOPEROXIDASE; PEROXIDASE; PHOSPHORUS 32; PLANT EXTRACT; XANTHINE OXIDASE; ZINC;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DNA ADDUCT; ION EXCHANGE CHROMATOGRAPHY; ISOTOPE LABELING; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; REDUCTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ANIMALS; ARISTOLOCHIC ACIDS; DNA ADDUCTS; HYDROGEN-ION CONCENTRATION; MALE; MICROSOMES; OXIDATION-REDUCTION; PEROXIDASES; PHENANTHRENES; RATS; RATS, SPRAGUE-DAWLEY; XANTHINE OXIDASE; ZINC;

EID: 0031408650     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/18.5.1055     Document Type: Article

References (34)

1. Woo, Y.-T., Lai, D.Y., Arcos, J.C. and Argus, M.F. (1988) Chemical Induction of Cancer IIIc. Academic Press, San Diego, CA.
2. Schmeiser, H.H., Bieler, C.A., Wiessler, M., van Ypersele de Strihou, C. and Cosyns, J.-P. (1996) Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy. Cancer Res., 56, 2025-2028.
3. Jackson, L., Kofman, S., Weiss, A. and Brodovsky, H. (1964) Aristolochic acid (NSC-50413): Phase 1 clinical study. Cancer Chemother. Rep., 42, 35-37.
4. Mengs, U., Lang, W. and Poch, J.A. (1982) The carcinogenic action of aristolochic acid. Arch. Toxicol., 51, 107-119.
5. Mengs, U. (1988) Tumour induction in mice following exposure to aristolochic acid. Arch. Toxicol., 61, 504-505.
6. 32P-post-labelling analysis of DNA adducts formed by aristolochic acidl and II. Carcinogenesis, 11, 1627-1633.
7. Schmeiser, H.H., Pool, B.L. and Wiessler, M. (1986) Identification and mutagenicity of metabolites of aristolochic acid formed by rat liver. Carcinogenesis, 7, 59-63.
8. Krumbiegel, G., Hallensleben, J., Meunicke, W., Rittmann, N. and Roth, H.J. (1987) Studies on the metabolism of aristolochic acidI and II. Xenobiotica, 17, 981-991.
9. Howard, P.C. and Beland, F.A. (1982) Xanthine oxidase catalysed binding of 1-nitropyrene to DNA: Biochem. Biophys. Res. Commun., 104, 727-731.
10. Kedderis, G.L. and Miwa, G.T. (1988) The metabolic activation of nitroheterocyclic therapeutic agents. Drug Metab. Rev., 19, 33-62.
11. Ohgaki, H., Negishi, C., Wakabayashi, K., Kusama, K., Sato, S. and Sugimura, T. (1984) Induction of sarcomas in rats by subscutaneous injection of dinitropyrenes. Carcinogenesis, 5, 583-585.
12. Djuric, Z., Fifer, E.K., Yamazoe, Y. and Beland, F.A. (1988) DNA binding by 1-nitropyrene and 1,6 dinitropyrene in vitro and in vivo: effects of nitroreductase induction. Carcinogenesis, 9, 357-364.
13. Goeptar, A.R., Scheerens, H. and Vermeulen, N.P.E. (1995) Oxygen and xenobiotic reductase activities of cytochrome P450. Crit. Rev. Toxicol., 25, 25-65.
14. Schmeiser, H.H., Schoepe, K.-B. and Wiessler, M. (1988) DNA adduct formation of aristolochic acidI and II in vitro and in vivo. Carcinogenesis, 9, 297-303.
15. Pfau, W., Schmeiser, H.H. and Wiessler, M. (1990) Aristolochic acid binds covalently to the exocyclic amino group of purine nucleotides in DNA. Carcinogenesis, 11, 313-319.
16. 6-adenyl arylation of DNA by aristolochic acidII and a synthetic model for the putative proximate carcinogen. Chem. Res. Toxicol., 4, 581-586.
17. 32P-post-labelling analysis using different chromatographic procedures. Carcinogenesis, 15, 1187-1192.
18. Kimura, T., Kodama, M. and Nagata, Ch. (1982) N-hydroxylation enzymes of carcinogenic aminoazo dyes: possible involvement of cytochrome P-448. Jpn. J. Cancer. Gann, 73, 455-462.
19. Stiborová, M., Asfaw, B., Anzenbacher, P., Lesetick, É,L. and Hodek, P. (1988) The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomes of rat livers. Cancer Lett., 40, 319-326.
20. Stiborová, M., Asfaw, B., Frei, E., Schmeiser, H.H. and Wiessler, M. (1995) Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct in DNA. Chem. Res. Toxicol., 8, 489-498.
21. 32P-postlabelling of DNA adducts derived from peroxidase activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I). Carcinogenesis, 11, 1843-1848.
22. 32P-post-labelling analysis of nonradioactive aromatic carcinogen-DNA adducts. Carcinogenesis, 3, 1081-1092.
23. 32P-post-labelling and high pressure liquid chromatographic analyses for 7,12-dimethylbenz[a]anthracene-DNA adducts. Carcinogenesis, 9, 633-638.
24. 32P-labelled nucleoside 3′,5′-bisphosphate adducts of polycyclic aromatic hydrocarbons. J. Chromatogr., 570, 65-76.
25. Broschard, T.H., Wiessler, M., von der Lieth, C.W. and Schmeiser, H.H. (1994) Translesional synthesis on DNA templates containing site-specifically placed deoxyadenosine and deoxyguanosine adducts formed by the plant carcinogen aristolochic acid. Carcinogenesis, 15, 2331-2340.
26. Broschard, T.H., Wiessler, M. and Schmeiser, H.H. (1995) Effect of site-specifically located aristolochic acid DNA adducts on in vitro DNA synthesis by human DNA polymerase α. Cancer Lett., 98, 47-56.
27. Beland, F.A. and Marques, M.M. (1994) DNA adducts of nitropolycyclic aromatic hydrocarbons. In Hemminki, K., Dipple, A., Shuker, D.E.G., Kadlubar, F.F., Segerback, D. and Bartsch, H. (eds) DNA Adducts: Identification and Biological Significance. IARC, Lyon, France, No. 125, pp. 229-244.
28. Swaminathan, S., Johnson, M.D., Reznikoff, C.A. and Bryanm, G.T. (1984) Bioconversion and macromolecular binding of 2-amino-4(5-nitro-2.furyl)thiazole by cultured rat urothelial cells., Cancer Res., 44, 5511-5516.
29. Perez-Reyes, D., Kalyanaraman, B. and Mason, R.P. (1980) The reductive metabolism of metronidazole and ronidazole by aerobic liver microsomes. Mol. Pharmacol., 17, 239-244.
30. Nakamura, M., Yamazaki, I., Kotani, T. and Ohtaki, S. (1985) Thyroid peroxidase selects the mechanism of either 1- or 2-electron oxidation of phenols, depending on their substituents. J. Biol. Chem., 260, 13546-13552.
31. Stock, B.H., Schreiber, J., Guenat, C., Mason, R.P., Bend, J.R. and Eling, T.S. (1986) Evidence for a free radical mechanism of styrene-glutathione conjugate formation catalysed by prostaglandin H synthase and horseradish peroxidase. J. Biol. Chem., 261, 15915-15922.
32. Ohnishi, T., Yamazaki, H., Iyanagi, T., Nakamura, T. and Yanazaki, I. (1969) One-electron-transfer reactions in biochemical systems. II. Reaction of free radicals formed in the enzymic oxidation. Biochim. Biophys. Acta, 172, 357-369.
33. Hillar, A. and Loewen, P.C. (1995) Comparison of isoniazid oxidation catalysed by bacterial catalase-peroxidase and horseradish peroxidase. Arch. Biochem. Biophys., 323, 438-446.
34. Thompson, D.C. and Eling, T.E. (1991) Reactive intermediates formed during the peroxidative oxidation of anidisine isomers. Chem. Res. Toxicol., 4, 474-481.