Mutagenicity of N-nitrosodiethanolamine in a V79-derived cell line expressing two human biotransformation enzymes

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 643, Issue 1-2, 2008, Pages 64-69

  Liu, Yungang ^a   Glatt, Hansruedi ^a  

^a GERMAN INSTITUTE OF HUMAN NUTRITION   (Germany)

Author keywords

2 Nitropropane; CYP2E1; Genetically engineered cell lines; Mutagenicity; N Nitrosodiethanolamine; N Nitrosodimethylamine; Sulphotransferase (SULT)

Indexed keywords

1 AMINOBENZOTRIAZOLE; 2 NITROPROPANE; BIS(2 HYDROXYETHYL)NITROSAMINE; CYTOCHROME P450 2E1; DIMETHYLNITROSAMINE; PENTACHLOROPHENOL; SULFOTRANSFERASE 1A1;

ANIMAL CELL; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; CYTOTOXICITY; GENE MUTATION; MUTAGENICITY; MUTATION RATE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ARYLSULFOTRANSFERASE; CELL PROLIFERATION; CELLS, CULTURED; CRICETINAE; CRICETULUS; CYTOCHROME P-450 CYP2E1; DIETHYLNITROSAMINE; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; MUTAGENICITY TESTS; MUTAGENS; MUTATION; NITROPARAFFINS; PROPANE;

MAMMALIA; RODENTIA;

EID: 49049098816     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrfmmm.2008.06.003     Document Type: Article

References (31)

1. IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans: N-Nitrosodiethanolamine (2000), International Agency for Research on Cancer, Lyon, France pp. 403-438
2. Mori Y., Yamazaki H., and Konishi Y. Mutagenicity of N-nitrosodiethanolamine in the Salmonella/microsome test. Mutat. Res. 192 (1987) 91-94
3. Kerklaan P., Mohn G., and Bouter S. Comparison of the mutagenic activity of dialkylnitrosamines in animal-mediated and in vitro assays using an Escherichia coli indicator. Carcinogenesis 2 (1981) 909-914
4. Knasmüller S., Stehlik G., and Mohn G. Studies on the metabolic activation of diethanolnitrosamine in animal-mediated and in vitro assays using Escherichia coli K-12 343/113 as an indicator. J. Cancer Res. Clin. Oncol. 112 (1986) 266-271
5. Eisenbrand G., Denkel E., and Pool B. Alcoholdehydrogenase as an activating enzyme for N-nitrosodiethanolamine (NDELA): in vitro activation of NDELA to a potent mutagen in Salmonella typhimurium. J. Cancer Res. Clin. Oncol. 108 (1984) 76-80
6. Henn I., Eisenbrand G., and Zankl H. Increased mutagenicity of N-nitrosodiethanolamine in human lymphocyte cultures after activation by alcohol dehydrogenase. J. Cancer Res. Clin. Oncol. 115 (1989) 445-448
7. Sterzel W., and Eisenbrand G. N-Nitrosodiethanolamine is activated in the rat to an ultimate genotoxic metabolite by sulfotransferase. J. Cancer Res. Clin. Oncol. 111 (1986) 20-24
8. Loeppky R.N., Fuchs A., Janzowski C., Humberd C., Goelzer P., Schneider H., and Eisenbrand G. Probing the mechanism of the carcinogenic activation of N-nitrosodiethanolamine with deuterium isotope effects: in vivo induction of DNA single-strand breaks and related in vitro assays. Chem. Res. Toxicol. 11 (1998) 1556-1566
9. Loeppky R.N. The mechanism of bioactivation of N-nitrosodiethanolamine. Drug Metab. Rev. 31 (1999) 175-193
10. Janzowski C., Scharner A., and Eisenbrand. Activation of nitrosamines by cytochrome P450 isoforms expressed in transfected V79 cells. Eur. J. Cancer Prevent. 5 (1996) 154
11. Glatt H.R., de Balle L., and Oesch F. Ethanol- or acetone-pretreatment of mice strongly enhances the bacterial mutagenicity of dimethylnitrosamine in assays mediated by liver subcellular fraction, but not in host-mediated assays. Carcinogenesis 2 (1981) 1057-1061
12. Glatt H.R. Sulfotransferases in the bioactivation of xenobiotics. Chem. Biol. Interact. 129 (2000) 141-170
13. Liu Y.-G., Muckel E., Doehmer J., and Glatt H.R. Phenol and hydroquinone induce gene mutations in V79-derived cells expressing human xenobiotic-metabolising enzymes. Nova Acta Leopoldina NF87 329 (2003) 231-237
14. Glatt H.R., Schneider H., and Liu Y.-G. V79-hCYP2E1-hSULT1A1, a cell line for the sensitive detection of genotoxic effects induced by carbohydrate pyrolysis products and other food-borne chemicals. Mutat. Res. 580 (2005) 41-52
15. Glatt H.R., Boeing H., Engelke C.E.H., Kuhlow A., Ma L., Pabel U., Pomplun D., Teubner W., and Meinl W. Human cytosolic sulphotransferases: genetics, characteristics, toxicological aspects. Mutat. Res. 482 (2001) 27-40
16. Ortiz de Montellano P.R., and Mathews J.M. Autocatalytic alkylation of the cytochrome P450 prosthetic haem group by 1-aminobenzotriazole: isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem. J. 195 (1981) 761-764
17. Emoto C., Murase S., Sawada Y., Jones B.C., and Iwasaki K. In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole. Drug Metab. Pharmacokinet. 18 (2003) 287-295
18. Meerman J.H.N., Sterenborg H.M., and Mulder G.J. Use of pentachlorophenol as long-term inhibitor of sulfation of phenols and hydroxamic acids in the rat in vivo. Biochem. Pharmacol. 32 (1983) 1587-1593
19. Glatt H.R. Sulphotransferases. In: Ioannides C. (Ed). Handbook of Enzyme Systems that Metabolise Drugs and Other Xenobiotics (2002), John Wiley & Sons, Sussex 353-439
20. Whittemore R.M., Pearce L.B., and Roth J.A. Purification and kinetic characterization of a phenol-sulfating form of phenol sulfotransferase from human brain. Arch. Biochem. Biophys. 249 (1986) 464-471
21. Tamási V., Hazai E., Porsmyr-Palmertz M., Ingelman-Sundberg M., Vereczkey L., and Monostory K. GYKI-47261, a new AMPA [2-amino-3-(3-hydroxymethylisoxazole-4-yl)propionic acid] antagonist, is a CYP2E1 inducer. Drug Metab. Dispos. 31 (2003) 1310-1314
22. Glatt H.R., Gemperlein I., Setiabudi F., Platt K.-L., and Oesch F. Expression of xenobiotic-metabolizing enzymes in propagatable cell cultures and induction of micronuclei by 13 compounds. Mutagenesis 5 (1990) 241-249
23. Schmalix W.A., Barrenscheen M., Landsiedel R., Janzowski C., Eisenbrand G., Gonzalez F., Eliasson E., Ingelman-Sundberg M., Perchermeier M., Greim H., and Doehmer J. Stable expression of human cytochrome P450 2E1 in V79 Chinese hamster cells. Eur. J. Pharmacol. 293 (1995) 123-131
24. Glatt H.R., Davis W., Meinl W., Hermersdörfer H., Venitt S., and Phillips D.H. Rat, but not human, sulfotransferase activates a tamoxifen metabolite to produce DNA adducts and gene mutations in bacteria and mammalian cells in culture. Carcinogenesis 19 (1998) 1709-1713
25. Kreis P., Brandner S., Coughtrie M.W.H., Pabel U., Meinl W., Glatt H.R., and Andrae U. Human phenol sulfotransferases hP-PST and hM-PST activate propane 2-nitronate to a genotoxicant. Carcinogenesis 21 (2000) 295-299
26. 6-hydroxyethyldeoxyguanosine adducts. Chem. Res. Toxicol. 15 (2002) 470-482
27. 6-hydroxyethyldeoxyguanosine DNA adducts produced by nitrosamine bident carcinogens. Chem. Res. Toxicol. 18 (2005) 556-565
28. Kollock R., Frank H., Seidel A., Meinl W., and Glatt H.R. Oxidation of alcohols and reduction of aldehydes derived from methyl- and dimethylpyrenes by cDNA-expressed human alcohol dehydrogenases. Toxicology 245 (2008) 65-75
29. Preussmann R., Spiegelhalder B., Eisenbrand G., Würtele G., and Hofmann I. Urinary excretion of N-nitrosodiethanolamine in rats following its epicutaneous and intratracheal administration and its formation in vivo following skin application of diethanolamine. Cancer Lett. 13 (1981) 227-231
30. Bonfanti M., Magagnotti C., Fanelli R., and Airoldi L. Comparative in vitro and in vivo β-oxidation of N-nitrosodiethanolamine in different animal species. Chem. Biol. Interact. 59 (1986) 203-210
31. Thielen S., Baum M., Hoffmann M., Loeppky R.N., and Eisenbrand G. Genotoxicity of glycidamide in comparison to (±)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide and α-acetoxy-N-nitroso-diethanolamine in human blood and in mammalian V79-cells. Mol. Nutr. Food Res. 50 (2006) 430-436