Abstract
Metabolic activation of 1,2-dichloroethane (DCE) and 1,2-dibromoethane (DBE) to forms able to bind covalently with DNA occurs in vitroeither by wat of microsomal or cytosolic pathways. The involvement of these two pathways is variable with respect to species or compound tested. Rat enzymes are generally more efficient than mouse enzymes in bioactivating haloalkanes and DBE is more reactive than DCE. This parallels both the previous report on in vivocomparative interaction and the higher genotoxicity of DBE.
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Abbreviations
- DCE:
-
dichloroethane
- DBE:
-
dibromoethane
- PB:
-
phenobarbitone
- ANOVA:
-
analysis of variance
References
ARFELLINI, G., BARTOLI, S., COLACCI, A., MAZZULLO, M., GALLI, M.C., PRODI, G., and GRILLI, S. (1983). Comparative interaction of dichloroethane and dibromoethane with rat and mouse nucleic acid. IRCS Med. Sci.11:81–82.
ARFELLINI, G., BARTOLI, S., COLACCI, A., MAZZULLO, M., GALLI, M.C., PRODI, G., and GRILLI, S. (1984).In vivo andin vitro binding of 1,2-dibromoethane and 1,2-dichloroethane to macromolecules in rat and mouse organs. J. Cancer Res. Clin. Oncol.108:204–213.
BANERJEE, S., and VAN DUUREN, B.L. (1979). Binding of carcinogenic halogenated hydrocarbons to cell macromolecules. J. Natl. Cancer Inst.63:707–711.
BANERJEE, S., VAN DUUREN, B.L., and ORUAMBO, F.I. (1980). Microsome-mediated covalent binding of 1,2-dichloroethane to lung microsomal protein and salmon sperm DNA. Cancer Res.40:2170–2173.
BRADFORD, M.M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem.73:248–254.
BURTON, K. (1956). A study on the conditions and mechanism of the diphenylamine reaction for the colorimetric estimation of deoxyribonucleic acid. Biochem. J.62:315–323.
FERRERI, A.M., ROCCHI, P., CAPUCCI, A., and PRODI, G. (1983). Induction of diphtheria toxin-resistant mutants in human cells by halogenated compounds. J. Cancer Res. Clin. Oncol.105:111–112.
GUENGERICH, F.P. (1977). Separation and purification of multiple forms of microsomal cytochrome P-450: Activities of different forms of cytochrome P-450 towards several compounds of environmental interest. J. Biol. Chem.252:3970–3979.
GUENGERICH, F.P., CRAWFORD, W.M., Jr., DOMORADZKI, J.Y., MACDONALD, T.L., and WATANABE, P.G. (1980).In vitro activation of 1,2-dichloroethane by microsomal and cytosolic enzymes. Toxicol. Appl. Pharmacol.55:303–317.
IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans. (1977). Vol. 15, IARC, Lyon, pp. 195–209.
IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans. (1979). Vol. 20, IARC, Lyon, pp. 429–448.
IARC Monographs on the evaluation of the carcinogenic risk of chemicals to humans. (1982). Suppl. 4, IARC, Lyon, pp. 124–126.
LIVESEY, J.C. and ANDERS, M.V. (1979).In vitro metabolism of 1,2-dihaloethanes to ethylene. Drug Metab. Disposition7:199–203.
LUTZ, K. (1979).In vivo covalent binding of organic chemicals to DNA as a quantitative indicator in the process of chemical carcinogenesis. Mutat. Res.65:289–356.
PEROCCO, P. and PRODI, G. (1981). DNA damage by haloalkanes in human lymphocytes culturedin vitro. Cancer Lett.13:213–218.
POWERS, M.B., VOELKER, R.W., PAGE, N.P., WEISBURGER, E.K., and KRAYBILL, H.F. (1975). Carcinogenicity of ethylene dibromide (EDB) and 1,2-dibromo-3-chloropropane (DBCP) after oral administration in rats and mice. Toxicol. Appl. Pharmacol.33:171–172.
RANNUG, U., SUNDVAL, A., and RAMEL, C. (1978). The mutagenic effect of 1,2-dichloroethane onSalmonella typhimurium. I. Activation through conjugation with glutathionein vitro. Chem. Biol. Interact.20:1–16.
RANNUG, U. (1980). Genotoxic effects of 1,2-dibromoethane and 1,2-dichloroethane. Mutat. Res.76:269–295.
SCHNEIDER, W.C (1945). Phosphorus compounds in animal tissues. I. Extraction and estimation of desoxypentose nuclei acide and of pentose nucleic acid. J. Biol. Chem.161:293–303.
SCHNEIDER, W.C. (1957). Determination of nucleic acids in tissues by pentose analysis. Meth. Enzymol.3: 680–684.
SUNDHEIMER, D.V., WHITE, R.D., BRENDEL, K., and SIPES, I.G. (1982). The bioactivation of 1,2-dibromoethane in rat hepatocytes: covalent binding to nucleic acids. Carcinogenesis3:1129–1133.
VAN BLADEREN, P.J., BREIMER, D.D., ROTEVEEL-SMIJS, G.M.T., DE KNIJFF, P., MOHN, G.R., VAN MEETEREN-WALCHLY, B., BIUJS, W., and VAN DER GEN, A. (1981). The relation between the structure of vicinal dihalogen compounds and their mutagenic activationvia conjugation to glutathione. Carcinogenesis2:499–505.
WILLIAMS, G.M., LASPIA, M.F., and DUNKEL, V.C. (1982). Reliability of the hepatocyte primary culture/DNA repair test in testing of coded carcinogens and noncarcinogens. Mutat. Res.97:359–370.
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Supported by grants from Ministero Pubblica Instruzione and from Ministero della Sanità (Contract No. 500.4/RSC/135/L/2353), Rome, Italy.
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Colacci, A., Mazzullo, M., Arfellini, G. et al. In vitro microsome- and cytosol-mediated binding of 1,2-dichloroethane and 1,2-dibromoethane with DNA. Cell Biol Toxicol 1, 45–55 (1985). https://doi.org/10.1007/BF00717790
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DOI: https://doi.org/10.1007/BF00717790