Toxic effects of paracetamol and related structures in V79 Chinese hamster cells

Mutagenesis

Volumn 3, Issue 1, 1988, Pages 51-56

  Holme, Jørn A ^a   Hongslo, Jan K ^a   Bjørnstad, Christine ^a   Harvison, Peter J ^a,b   Nelson, Sidney D ^a,b  

^a NORWEGIAN INSTITUTE OF PUBLIC HEALTH   (Norway)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPHENOL; PARACETAMOL; RADIOISOTOPE;

ANIMAL CELL; CELL CULTURE; CELL STRAIN V 79; CYTOLOGY; DNA SYNTHESIS INHIBITION; HAMSTER; HEREDITY; MUTAGENICITY; NONHUMAN; SISTER CHROMATID EXCHANGE;

ACETAMINOPHEN; ANIMAL; CELL SURVIVAL; CELLS, CULTURED; CRICETULUS; DNA REPLICATION; HAMSTERS; SISTER CHROMATID EXCHANGE; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0023869715     PISSN: 02678357     EISSN: None     Source Type: Journal    
DOI: 10.1093/mutage/3.1.51     Document Type: Article

References (41)

1. Alves, P. and Jonasson, J. (1978) New staining method for the detection of sister chromatid exchanges in BrdU-labelled chromosomes. J. Cell. Sci., 32, 185–195.
2. Ashby, J. (1985) The genotoxicity of sodium saccharin and sodium chloride in relation to their cancer-promoting properties. Food Chem. Toxicol., 23, 507–519.
3. Boyd, E.M. and Bereczky, G.M. (1966) Liver necrosis from paracetamol. Br. J. Pharmacol., 26, 606–614.
4. Dahlin, D.C., Miwa, G.T., Lu, A.Y.H. and Nelson, S.D. (1984) N-Acetyl-p-benzoquinone imine: a cytochrome P-450 mediated oxidation product of acetaminophen. Proc. Natl. Acad. Sci. USA, 81, 1327–1331.
5. Dybing, E., Holme, J.A., Gordon, W.P., Søderlund, E.J., Dahlin, D.C. and Nelson, S.D. (1984) Genotoxicity studies with paracetamol. Mutat. Res., 138, 21–32.
6. Fernando, C.R., Calder, I.C. and Ham, K.N. (1980) Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2, 6-dimethyl and N-acetyl-3, 5-dimethyl-p-benzoquinone imines. J. Med. Chem., 23, 1153–1158.
7. Fischer, V. and Mason, R.P. (1984) Stable free radical and benzoquinone imine metabolites of an acetaminophen analogue. J. Biol. Chem., 259, 10284–10288.
8. Fischer, W., West, P.R., Nelson, S.D., Harvison, P.J. and Mason, R.P. (1985) Formation of 4-aminophenoxyl free radical from the acetaminophen metabolite N-acetyl-p-benzoquinone imine. J. Biol. Chem., 21, 11446–11450.
9. Flaks, A. and Flaks, B. (1983) Induction of liver cell tumors in IF mice by paracetamol. Carcinogenesis, 4, 363–368.
10. Flaks, B., Flaks, A. and Shaw, A.P.W. (1985) Induction by paracetamol of bladder and liver tumors in the rat. Acta Pathol. Microbiol. Immunol. Scand., A93, 367–377.
11. Guengerich, F.P. and Liebler, D.C. (1985) Enzymatic activation of chemicals to toxic metabolites. CRC Crit. Rev. Toxicol., 14, 259–307.
12. Harvison, P.J., Egan, P.W., Gale, P.H. and Nelson, S.D. (1986) Acetaminophen as a cosubstrate and inhibitor of prostaglandin H synthase. In Kocsis, J.J., Jollow, D.J., Witmer, C.M., Nelson, J.O. and Snyder, R. (eds), Biological Reactive Intermediates III, Adv. Exp. Med. Biol., Vol. 197, pp. 739–747.
13. Hayward, N.K. and Lavin, M.F. (1987) Inhibition of DNA, RNA and protein synthesis and chromatin alteration by N-hydroxyphenacetin. Xenobiotica, 17, 115–124.
14. Hayward, N.K., Lavin, M.F., and Craswell, P.W. (1982) Inhibition of DNA synthesis and alteration to DNA structure by the phenacetin analog p-aminophenol. Biochem. Pharmacol., 31,. 1425–1429.
15. Hayward, N.K., Calder, I. and Lavin, M.F. (1986) Effect of N-hydroxyparacetamol on DNA, RNA and protein synthesis and chromatin structure. Mol. Pharmacol., 29, 478–483.
16. Holme, J.A. and Søderlund, E. (1986) Species differences in cytotoxic effects of phenacetin and paracetamol in primary monolayer cultures of hepatocytes. Mutat. Res., 164, 167–175.
17. Holme, J.A., Dahlin, D.C., Nelson, S.D. and Dybing, E. (1984) Cytotoxic effects of N-acetyl-p-benzoquinone imine, a common arylating intermediate of paracetamol and N-hydroxyparacetamol. Biochem. Pharmacol., 33, 401–406.
18. Holme, J.A., Hongslo, J., Søderlund, E., Brunborg, G., Christensen, T., Alexander, J. and Dybing, E. (1987) Comparative genotoxic effects of IQ and MeIQ in Salmonella typhimurium and cultured mammalian cells. Mutat. Res., 187, 181–190.
19. Hongslo, J.K., Christensen, T., Bjørnstad, C., Støttum, A. and Holme, J.A. (1986) Genotoxic effect of paracetamol in V79 Chinese Hamster cells. Abstracts. XVI Annual Meeting on the European Environmental Mutagen Society, Brussels, p. 20.
20. Hongslo, J.K., Christensen, T., Brunborg, G., Bjømstad, C. and Holme, J.A. (1987) Genotoxic effects of paracetamol in V79 Chinese hamster cells. Mutat. Res., in press.
21. Ishii, Y. and Bender, M.A. (1980) Effect of inhibitors of DNA synthesis on spontaneous and ultraviolet light-induced sister-chromatid exchanges in Chinese hamster cells. Mutat. Res., 79, 19–32.
22. Kato, H. (1974) Possible role of DNA synthesis in formation of sister chromatid exchanges. Nature, 252, 739–941.
23. Lambert, B., Chu, E.H.Y., Carli, L.De, Erling, U.H., Evans, H.J., Hayashi, M., Thilly, W.G. and Vainio, H. (1986) Report 7. Assays for genetic changes in mammalian cells. In Montesano, R., Batsch, H., Vainio, H., Wilbourn, J. and Yamasaki, H. (eds), Long-term and Short-term Assays for Carcinogens: A Critical Appraisal. LARC Scientific Publications, no. 83 IARC, Lyon, pp. 167–243.
24. Latt, S.A., Allen, J., Bloom, S.E., Carrano, A., Falke, E., Kram, D., Schneider, E., Schreck, R., Tice, R., Whitfield, B. and Wolff, S. (1981) Sister-chromatid exchanges: a report of the Gene-Tox program. Mutat. Res., 87, 17–62.
25. Lim, M., Liu, L.F., Jacobson-Kram, D. and Williams, J.R. (1986) Induction of sister chromatid exchanges by inhibitors of topoisomerases. Cell Biol. Toxicol., 2, 485–494.
26. Mitchell, J.R., Jollow, D.J., Potter, W.Z., Gilette, J.R. and Brodie, B.B. (1973) Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J. Pharmacol. Exp. Ther., 187, 211–217.
27. Morris, S.M. and Heflich, R.H. (1984) A comparison of the toxic and SCE-inducing effects of inhibitors of ADP-ribosyl transferase in Chinese hamster ovary cells. Mutat. Res., 126, 63–71.
28. Oikawa, A., Tohda, H., Kanai, M., Miwa, M. and Sugimura, T. (1980) Inhibitors of poly (adenosine diphosphate ribose) polymerase induce sister chromatid exchanges. Biochem. Biophys. Res. Commun., 97, 1311–1316.
29. Painter, R.M. (1980) A replication model for sister chromatid exchange. Mutat. Res., 70, 337–341.
30. Painter, R.N. and Howard, R. (1982) The HeLa DNA-synthesis inhibition test as a rapid screen for mutagenic carcinogens. Mutat. Res., 92, 427–437.
31. 2 mouse embryo cells. Environ. Mutagenesis, 9 (Suppl. 8), 84.
32. Perry, P.E. and Thomson, E.J. (1984) The methodology of sister chromatid exchanges. In Kilbey, B.J., Legator, M., Nichols, W. and Ramel, C. (eds), Handbook of Mutagenicity Test Procedures. Elsevier, Amsterdam, pp. 269–290.
33. Pommier, Y., Zwelling, L.A., Kao-Shan, C.-S., Whang-Peng, J. and Bradley, M.O. (1985) Correlations between intercalator-induced DNA strand breaks and sister chromatid exchanges, mutations and cytotoxicity in Chinese hamster cells. Cancer Res., 45, 3143–3149.
34. Potter, D.W. and Hinson, J.A. (1987a) Mechanisms of acetaminophen oxidation to N-acetyl-p-benzoquinone imine by horseradish peroxidase and cytochrome P-450. J. Biol. Chem., 262, 966–973.
35. Potter, D.W. and Hinson, J.A. (1987b) The 1- and 2-electron oxidation of acetaminophen catalyzed by prostaglandin H synthetase. J. Biol. Chem., 262, 974–980.
36. Prescott, L.F., Wright, N., Roscoe, P. and Brown, S.S. (1971) Plasma paracetamol half-life and hepatic necrosis in patients with paracetamol overdosage. Lancet, i, 519–522.
37. Sasaki, M., Yoshida, S. and Hiraga, K. (1983) Additional effect of acetaminophen on the mutagenicity and clastogenicity of N-methyl-N′-nitro-N-nitrosoguanidine in cultured Chinese hamster CHO-KI cells. Mutat. Res., 122, 367–372.
38. Schwartz, J.L., Morgan, W.F., Kapp, L.N. and Wolff, S. (1983) Effects of 3-amino-benzamide on DNA synthesis and cell cycle progression in Chinese hamster ovary cells. Exp. Cell Res., 143, 377–382.
39. Streeter, S.J., Dahlin, D.C., Nelson, S.D. and Baillie, T.A. (1984) The covalent binding of acetaminophen to protein: evidence for cysteine residues as major sites of arylation in vitro. Chem.-Biol. Interactions, 48, 349–366.
40. Wolff, S. (1977) Sister chromatid exchange. Annu. Rev. Genet., 11, 183–201.
41. Wolff, S., Bodycote, J. and Painter, R.B. (1974) Sister chromatid exchanges induced in Chinese hamster cells by UV irradiation of different stages of the cell cycle: the necessity for cells to pass through S. Mutat. Res., 25, 73–81.