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Chemical Compound Review

Dowfume W 85     1,2-dibromoethane

Synonyms: Sanhyuum, Soilbrom, Soilfume, Aadibroom, Ethylene Bromide, ...
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Disease relevance of sym-Dibromoethane

  • 1,2-Dibromoethane was the only compound that induced a significant incidence (p less than 0.05) of skin papillomas, skin carcinomas, and lung tumors by repeated skin application [1].
  • Paradoxical enhancement of the toxicity of 1,2-dibromoethane by O6-alkylguanine-DNA alkyltransferase [2].
  • The presence of the DNA repair protein O(6)-alkylguanine-DNA alkyltransferase (AGT) paradoxically increases the mutagenicity and cytotoxicity of 1,2-dibromoethane (DBE) in Escherichia coli [2].
  • Integration of trapping and desorption methods with the Salmonella microsuspension bioassay was demonstrated with EDB and 4-NB recoveries from air; chemical analysis and bioassay gave comparable results (within 10%) [3].
  • Experiments were designed to investigate the expression of three cell-cycle-dependent proto-oncogenes in response to two different types of proliferative stimuli: compensatory cell proliferation after partial hepatectomy (PH) or CCl4 and liver hyperplasia induced by the mitogens ethylene dibromide (EDB) and cyproterone acetate (CPA) [4].

High impact information on sym-Dibromoethane

  • The binding of EDB to these macromolecules was augmented with increasing concentrations of microsomes [5].
  • The binding of EDB or EDC with proteins was not significant when denatured microsomes were used or when DNA was used in the absence of microsomes [5].
  • In studies carried out with isolated hepatocytes, equimolar amounts of 1,2-dibromoethane and endogenous GSH were also bound to intracellular DNA and RNA and extracellular DNA [6].
  • Enzymatic hydrolysis of calf thymus DNA labeled with 1,2-dibromoethane in the presence of GSH and GSH S-transferase and subsequent high-performance liquid chromatography of the residues yielded a major fraction, which also was found to contain radiolabel derived from GSH [6].
  • The major DNA adduct formed from the carcinogen ethylene dibromide (1,2-dibromoethane, EDB) is S-[2-(N7-guanyl)ethyl]glutathione, resulting from the reaction of guanyl residues with the half-mustard S-(2-bromoethyl)glutathione, which is generated by glutathione S-transferase-catalyzed conjugation of EDB with glutathione [7].

Chemical compound and disease context of sym-Dibromoethane


Biological context of sym-Dibromoethane


Anatomical context of sym-Dibromoethane


Associations of sym-Dibromoethane with other chemical compounds


Gene context of sym-Dibromoethane


Analytical, diagnostic and therapeutic context of sym-Dibromoethane


  1. Carcinogenicity of halogenated olefinic and aliphatic hydrocarbons in mice. Van Duuren, B.L., Goldschmidt, B.M., Loewengart, G., Smith, A.C., Melchionne, S., Seldman, I., Roth, D. J. Natl. Cancer Inst. (1979) [Pubmed]
  2. Paradoxical enhancement of the toxicity of 1,2-dibromoethane by O6-alkylguanine-DNA alkyltransferase. Liu, L., Pegg, A.E., Williams, K.M., Guengerich, F.P. J. Biol. Chem. (2002) [Pubmed]
  3. Determination of volatile and semivolatile mutagens in air using solid absorbents and supercritical fluid extraction. Wong, J.M., Kado, N.Y., Kuzmicky, P.A., Ning, H.S., Woodrow, J.E., Hsieh, D.P., Seiber, J.N. Anal. Chem. (1991) [Pubmed]
  4. Liver hyperplasia is not necessarily associated with increased expression of c-fos and c-myc mRNA. Coni, P., Pichiri-Coni, G., Ledda-Columbano, G.M., Rao, P.M., Rajalakshmi, S., Sarma, D.S., Columbano, A. Carcinogenesis (1990) [Pubmed]
  5. Binding of carcinogenic halogenated hydrocarbons to cell macromolecules. Banerjee, S., Van Duuren, B.L. J. Natl. Cancer Inst. (1979) [Pubmed]
  6. Evidence for formation of an S-[2-(N7-guanyl)ethyl]glutathione adduct in glutathione-mediated binding of the carcinogen 1,2-dibromoethane to DNA. Ozawa, N., Guengerich, F.P. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  7. Covalent binding of 1,2-dihaloalkanes to DNA and stability of the major DNA adduct, S-[2-(N7-guanyl)ethyl]glutathione. Inskeep, P.B., Koga, N., Cmarik, J.L., Guengerich, F.P. Cancer Res. (1986) [Pubmed]
  8. Carcinogenicity studies on halogenated hydrocarbons. Weisburger, E.K. Environ. Health Perspect. (1977) [Pubmed]
  9. Metabolism of 1,2-dibromoethane in the human fetal liver. Kulkarni, A.P., Edwards, J., Richards, I.S. Gen. Pharmacol. (1992) [Pubmed]
  10. Alpha1-adrenergic receptors and their significance to chemical-induced nephrotoxicity--a brief review. Stedeford, T., Cardozo-Pelaez, F., Vultaggio, B., Muro-Cacho, C., Luzardo, G.E., Harbison, R.D. Res. Commun. Mol. Pathol. Pharmacol. (2001) [Pubmed]
  11. Characterization of the hepatic DNA damage caused by 1,2-dibromoethane using the alkaline elution technique. White, R.D., Sipes, I.G., Gandolfi, A.J., Bowden, G.T. Carcinogenesis (1981) [Pubmed]
  12. Molecular mechanisms of dibromoalkane cytotoxicity in isolated rat hepatocytes. Khan, S., Sood, C., O'Brien, P.J. Biochem. Pharmacol. (1993) [Pubmed]
  13. Metabolic activation of 1,2-dibromoethane to a free radical intermediate by rat liver microsomes and isolated hepatocytes. Tomasi, A., Albano, E., Dianzani, M.U., Slater, T.F., Vannini, V. FEBS Lett. (1983) [Pubmed]
  14. Conjugative metabolism of 1,2-dibromoethane in mitochondria: disruption of oxidative phosphorylation and alkylation of mitochondrial DNA. Thomas, C., Will, Y., Schoenberg, S.L., Sanderlin, D., Reed, D.J. Biochem. Pharmacol. (2001) [Pubmed]
  15. Cell proliferation in rat kidney induced by 1,2-dibromoethane. Ledda-Columbano, G.M., Columbano, A., Coni, P., Curto, M., Faa, G., Pani, P. Toxicol. Lett. (1987) [Pubmed]
  16. Enhancement of BALB/c 3T3 cells transformation by 1,2-dibromoethane promoting effect. Colacci, A., Vaccari, M., Perocco, P., Da Vià, C., Silingardi, P., Manzini, E., Horn, W., Grilli, S. Carcinogenesis (1996) [Pubmed]
  17. Induction of DNA repair in rat spermatocytes and hepatocytes by 1,2-dibromoethane: the role of glutathione conjugation. Working, P.K., Smith-Oliver, T., White, R.D., Butterworth, B.E. Carcinogenesis (1986) [Pubmed]
  18. Ethylene dibromide: negative results with the mouse dominant lethal assay and the electrophoretic specific-locus test. Barnett, L.B., Lovell, D.P., Felton, C.F., Gibson, B.J., Cobb, R.R., Sharpe, D.S., Shelby, M.D., Lewis, S.E. Mutat. Res. (1992) [Pubmed]
  19. Lipid peroxidation and irreversible cell damage: synergism between carbon tetrachloride and 1,2-dibromoethane in isolated rat hepatocytes. Danni, O., Chiarpotto, E., Aragno, M., Biasi, F., Comoglio, A., Belliardo, F., Dianzani, M.U., Poli, G. Toxicol. Appl. Pharmacol. (1991) [Pubmed]
  20. Metabolic activation of halogenated hydrocarbons in the conjunctival epithelium and excretory ducts of the intraorbital lacrimal gland in mice. Brittebo, E.B., Eriksson, C., Brandt, I. Exp. Eye Res. (1991) [Pubmed]
  21. Liver AP-1 activation due to carbon tetrachloride is potentiated by 1,2-dibromoethane but is inhibited by alpha-tocopherol or gadolinium chloride. Camandola, S., Aragno, M., Cutrin, J.C., Tamagno, E., Danni, O., Chiarpotto, E., Parola, M., Leonarduzzi, G., Biasi, F., Poli, G. Free Radic. Biol. Med. (1999) [Pubmed]
  22. Comparative in vivo genotoxicity and acute hepatotoxicity of three 1,2-dihaloethanes. Storer, R.D., Conolly, R.B. Carcinogenesis (1983) [Pubmed]
  23. Activation of bis-electrophiles to mutagenic conjugates by human O6-alkylguanine-DNA alkyltransferase. Valadez, J.G., Liu, L., Loktionova, N.A., Pegg, A.E., Guengerich, F.P. Chem. Res. Toxicol. (2004) [Pubmed]
  24. Mutagenicity of 1,2-dichloroethane and 1,2-dibromoethane in two human lymphoblastoid cell lines. Crespi, C.L., Seixas, G.M., Turner, T.R., Ryan, C.G., Penman, B.W. Mutat. Res. (1985) [Pubmed]
  25. The use of human in vitro metabolic parameters to explore the risk assessment of hazardous compounds: the case of ethylene dibromide. Ploemen, J.P., Wormhoudt, L.W., Haenen, G.R., Oudshoorn, M.J., Commandeur, J.N., Vermeulen, N.P., de Waziers, I., Beaune, P.H., Watabe, T., van Bladeren, P.J. Toxicol. Appl. Pharmacol. (1997) [Pubmed]
  26. Roles of horizontal gene transfer and gene integration in evolution of 1,3-dichloropropene- and 1,2-dibromoethane-degradative pathways. Poelarends, G.J., Kulakov, L.A., Larkin, M.J., van Hylckama Vlieg, J.E., Janssen, D.B. J. Bacteriol. (2000) [Pubmed]
  27. The role of human O(6)-alkylguanine-DNA alkyltransferase in promoting 1,2-dibromoethane-induced genotoxicity in Escherichia coli. Liu, H., Xu-Welliver, M., Pegg, A.E. Mutat. Res. (2000) [Pubmed]
  28. Isolation and characterization of N7-guanyl adducts derived from 1,2-dibromo-3-chloropropane. Humphreys, W.G., Kim, D.H., Guengerich, F.P. Chem. Res. Toxicol. (1991) [Pubmed]
  29. Cloning, biochemical properties, and distribution of mycobacterial haloalkane dehalogenases. Jesenská, A., Pavlová, M., Strouhal, M., Chaloupková, R., Tesínská, I., Monincová, M., Prokop, Z., Bartos, M., Pavlík, I., Rychlík, I., Möbius, P., Nagata, Y., Damborsky, J. Appl. Environ. Microbiol. (2005) [Pubmed]
  30. Decrease of hepatic mitochondrial glutathione and mitochondrial injury induced by 1,2-dibromoethane in the rat in vivo: effect of diethylmaleate pretreatment. Botti, B., Bini, A., Calligaro, A., Meletti, E., Tomasi, A., Vannini, V. Toxicol. Appl. Pharmacol. (1986) [Pubmed]
  31. Quantitative analysis of embryonic kidney impairment by confocal microscopy and stereology: effect of 1,2-dibromoethane in the chick mesonephros. Náprstková, I., Radochová, B., Novotná, B., Jirkovská, M., Janácek, J., Kubínová, L. Br. Poult. Sci. (2005) [Pubmed]
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