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On the Possible Role of the Miscoding DNA-Lesions, 1,N6-Etheno-Adenine and 3,N4-Ethenocytosine, in Vinyl Chloride-Induced Mutagenesis and Carcinogenesis

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Chromosome Damage and Repair

Part of the book series: NATO Advanced Study Institutes Series ((NSSA,volume 40))

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Abstract

Chloroacetaldehyde (CAA) and chloroethylene oxide (CEO), two reactive metabolites of vinyl chloride, were used to introduce increasing amounts of 1,N6-ethenoadenine (εA) and 3,N4-etheno cytosine (εC) residues in poly(dA) and poly(dC), respectively. The modified polynucleotides were assayed with E. coli DNA polymerase I for their template activity and for misincorporation. The miscoding properties of εA and εC that we observed may explain the mutagenic effects reported for vinyl chloride and its metabolites; these lesions may also represent one of the initial steps in vinyl chloride or CEO-induced carcinogenesis.

This work was supported in part by a contract, no. NO1 CP-55630, from the National Cancer Institute, USPHS.

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References

  1. J.L. Creech and M.N. Johnson, Angiosarcoma of the liver in the manufacture of polyvinyl chloride, J. Occup. Med., 16: 150151 (1974).

    Google Scholar 

  2. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 19, International Agency for Research on Cancer, Lyon, France (1979).

    Google Scholar 

  3. H. Bartsch and R. Montesano, Mutagenic and carcinogenic effects of vinyl chloride, Mutat. Res., 32: 93–114 (1975).

    CAS  Google Scholar 

  4. A. Barbin, H. Brésil, A. Croisy, P. Jacquignon, C. Malaveille, R. Montesano, and H. Bartsch, Liver-microsome-mediated formation of alkylating agents from vinyl bromide and vinyl chloride, Biochem. Biophys. Res. Commun., 67: 596–603 (1975).

    Article  CAS  Google Scholar 

  5. E. Huberman, H. Bartsch, and L. Sachs, Mutation induction in Chinese hamster V79 cells by two vinyl chloride metabolites, chloroethylene oxide and 2-chloroacetaldehyde, Int. J. Cancer, 16: 639–644 (1975).

    Article  CAS  PubMed  Google Scholar 

  6. N. Loprieno, R. Barale, S. Baroncelli, H. Bartsch, G. Bronzetti, A. Cammellini, C. Corsi, D. Frezza, R. Nieri, C. Leporini, D. Rosellini, and A.M. Rossi, Induction of gene mutations and gene conversions by vinyl chloride metabolites in yeast, Cancer Res., 36: 253–257 (1977).

    Google Scholar 

  7. C. Malaveille, H. Bartsch, A. Barbin, A.M. Camus, R. Montesano, A. Croisy, and P. Jacquignon, Mutagenicity of vinyl chloride, chloroethyleneoxide, chloroacetaldehyde and chloroethanol, Biochem. Biophys. Res. Commun., 63: 363–370 (1975).

    Article  CAS  Google Scholar 

  8. U. Rannug, R. Göthe, and C.A. Wachtmeister, The mutagenicity of chloroethylene oxide, chloroacetaldehyde, 2-chloroethanol and chloroacetic acid, conceivable metabolites of vinyl chloride, Chem.-biol. Interactions, 12: 251–263 (1976).

    CAS  Google Scholar 

  9. F. Zajdela, A. Croisy, A. Barbin, C. Malaveille, L. Tomatis, and H. Bartsch, Carcinogenicity of chloroethylene oxide, an ultimate reactive metabolite of vinyl chloride, and bis(chloromethyl)ether after subcutaneous administration and in initiation-promotion experiments in mice, Cancer Res., 40: 352–356 (1980).

    PubMed  CAS  Google Scholar 

  10. G. Bonse, T. Urban, D. Reichert, and D. Henschler, Chemical reactivity, metabolic oxirane formation and biological reactivity of chlorinated ethylenes in the isolated perfused rat liver preparation, Biochem. Pharmacol., 24: 1829–1834 (1975).

    CAS  Google Scholar 

  11. R.J. Laib and H.M. Bolt, Alkylation of RNA by vinyl chloride metabolites in vitro and in vivo: formation of 1,N6-ethenoadenosine, Toxicology, 8: 185–195 (1977).

    Article  CAS  PubMed  Google Scholar 

  12. R.J. Laib and H.M. Bolt, Formation of 3,N4-ethenocytidine moieties in RNA by vinyl chloride metabolites in vitro and in vivo, Arch. Toxicol., 39: 235–240 (1978).

    CAS  Google Scholar 

  13. J.R. Barrio, J.A. Secrist III, and N.J. Leonard, Fluorescent adenosine and cytidine derivatives, Biochem. Biophys. Res. Commun., 46: 597–604 (1972).

    Article  CAS  Google Scholar 

  14. T. Green and D.E. Hathway, Interactions of vinyl chloride with rat-liver DNA in vivo, Chem.-biol. Interactions, 22: 211–224 (1978).

    CAS  Google Scholar 

  15. L.L. Gerchman and D.B. Ludlum, The properties of 06-methylguanine in templates for RNA polymerase, Biochim. Biophys. Acta, 308: 310–316 (1973).

    CAS  Google Scholar 

  16. P.J. Abbott and R. Saffhill, DNA synthesis with methylated poly(dC-dG) templates. Evidence for a competitive nature to miscoding by 06-methylguanine, Biochim. Biophys. Acta, 562: 51–61 (1979).

    CAS  Google Scholar 

  17. A.E. Pegg, Formation and metabolism of alkylated nucleosides: possible role in carcinogenesis by nitroso compounds and alkylating agents, Adv. Cancer Res., 25: 195–269 (1977).

    Article  CAS  Google Scholar 

  18. C.W. Shearman and L.A. Loeb, Effects of depurination on the fidelity of DNA synthesis, J. Mol. Biol., 128: 197–218 (1979).

    Article  CAS  PubMed  Google Scholar 

  19. C.W. Shearman and L.A. Loeb, Effects of depurination on the fidelity of DNA synthesis, J. Mol. Biol., 128: 197–218 (1979).

    Article  CAS  PubMed  Google Scholar 

  20. J. Biernat, J. Ctssiolk, P.., ßérnicki,.R.W4 Adamtak, W.1. Krzyzosiak, and M. Wiewigrowski, New observations concerning the chloroacetaldehyde reaction with some tRNA constituents. Stable intermediates, kinetics and selectivity of the reaction, Nucleic Acids Res., 5: 789–804 (1978).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. J. McCann, V. Simenon, D. Streitwieser, and B.N. Ames., Mutagenicity of chloroacetaldehyde, a possible metabolic product of 1,2-dichloroethane (ethylene dichloride), chloroethanol (ethylene chlorohydrin), vinyl chloride, and cyclophosphamide, Proc. Nati. Acad. Sci. USA, 72: 3190–3193 (1975).

    Article  CAS  Google Scholar 

  22. U. Rannug, A. Johanson, C. Reuel, and C. Wachtmeister, Mutagenicity of vinyl chloride after metabolic activation, Ambio, 3: 194–197 (1974).

    CAS  Google Scholar 

  23. P.J. Abbott and R. Saffhill, DNA synthesis with methylated poly(dA-dT) templates: possible role of 04-methylthymine as a pro-mutagenic base, Nucleic Acids Res., 4: 761–769 (1977).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. B. Singer, N-Nitroso alkylating agents: formation and persistence of alkyl derivatives in mammalian nucleic acids as contributing factors in carcinogenesis, J. Nati. Cancer Inst., 62: 1329–1339 (1979).

    CAS  Google Scholar 

  25. H. Ottenwälder, R.J. Laib, and H.M. Bolt, Alkylation of RNA by vinyl bromide metabolites in vitro and in vivo, Arch. Toxicol., 41: 279–286 (1979).

    Google Scholar 

  26. D.B. Ludlum, B.S. Kramer, J. Wang, and C. Fenselau, Reaction of 1,3-bis(2-chloroethyl)-1 nitrosourea with synthetic poly-nucleotides, Biochemistry, 14: 5480–5485 (1975).

    Article  CAS  PubMed  Google Scholar 

  27. W.P. Tong and D.B. Ludlum, Mechanism of action of the nitrosoureas-III. Reaction of bis-chloroethyl nitrosourea and bis-fluoroethyl nitrosourea with adenosine, Biochem. Pharmacol., 28: 1175–1179 (1979).

    CAS  Google Scholar 

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Authors and Affiliations

  1. International Agency for Research on Cancer, 150 cours Albert-Thomas, F-69372, Lyon Cédex 2, France

    Alain Barbin & Helmut Bartsch

  2. Free University of Brussels, B-1640, Rhode-St-Genèse, Belgium

    Philippe Lecomte & Miroslav Redman

Authors
  1. Alain Barbin
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  2. Helmut Bartsch
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  3. Philippe Lecomte
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  4. Miroslav Redman
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Editor information

Editors and Affiliations

  1. Norwegian Defense Research Establishment, Kjeller, Norway

    Erling Seeberg

  2. University of Bergen, Bergen, Norway

    Kjell Kleppe

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© 1981 Plenum Press, New York

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Barbin, A., Bartsch, H., Lecomte, P., Redman, M. (1981). On the Possible Role of the Miscoding DNA-Lesions, 1,N6-Etheno-Adenine and 3,N4-Ethenocytosine, in Vinyl Chloride-Induced Mutagenesis and Carcinogenesis. In: Seeberg, E., Kleppe, K. (eds) Chromosome Damage and Repair. NATO Advanced Study Institutes Series, vol 40. Springer, New York, NY. https://doi.org/10.1007/978-1-4684-7956-0_53

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  • DOI: https://doi.org/10.1007/978-1-4684-7956-0_53

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4684-7958-4

  • Online ISBN: 978-1-4684-7956-0

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