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Chemical Compound Review

AG-E-20930     2-bromoethanal

Synonyms: LS-7233, CTK4D3979, AKOS006279610, BRN 0969223, AC1L2Y3K, ...
 
 
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Disease relevance of BRN 0969223

 

High impact information on BRN 0969223

  • Supercoiled plasmid DNAs (at bacterial superhelical density) harboring the homopurine-homopyrimidine sequence, poly(dG)-poly(dC), were reacted with bromoacetaldehyde (BAA), a reagent that reacts with unpaired DNA bases [3].
  • Plasmid pT181 DNA secondary structures have been analyzed in vitro by nuclease S1 digestion and in vivo by bromoacetaldehyde treatment [4].
  • These altered DNA structures are found at reproducible positions relative to the beta A-globin gene regardless of whether the bromoacetaldehyde is presented to intact erythrocytes, erythrocyte nuclei, or the beta A-globin gene itself carried in pBR322 as purified supercoiled DNA [5].
  • A region of about 200 base pairs 5' to the chicken beta A-globin gene, which contains sites sensitive to nuclease S1, to several restriction endonucleases, and to very low levels of DNase I, also contains DNA structures that are preferentially sensitive to bromoacetaldehyde [5].
  • Studies with labeled 2-bromoacetaldehyde indicate that the slow kinetics of DNA binding by this compound is responsible in part for this phenomenon [6].
 

Biological context of BRN 0969223

 

Anatomical context of BRN 0969223

 

Associations of BRN 0969223 with other chemical compounds

  • Chloroacetaldehyde, like bromoacetaldehyde, was found to be a specific probe for detecting unpaired DNA bases in supercoiled plasmid DNA [11].
  • These results coupled with analyses with chemical (diethyl pyrocarbonate, osmium tetroxide, and bromoacetaldehyde) and enzymatic (S1 nuclease, T7 gene 3 product, and MHhaI) probes indicated that the entire sequence was adopting a left-handed helix in each case [12].
  • Two possible mechanisms for the reported carcinogenic synergism between ethylene dibromide (EDB) and disulfiram have been investigated in vivo and in vitro, the first involving increased production of an EDB-derived glutathione mustard and the second increased production of bromoacetaldehyde [13].
  • A previous method of determination of adenine compounds by high-performance liquid chromatography, using bromoacetaldehyde as a fluorescent reagent and a column of Hitachi gel No. 3012-N, was improved and extended to biological materials, especially to measure enzyme activities [14].
 

Gene context of BRN 0969223

  • 2-Bromoethylene oxide and 2-bromoacetaldehyde, suspected metabolites of VBR, were synthesized and found to be substrates for rat liver epoxide hydrolase and equine liver alcohol dehydrogenase, respectively [6].
  • Flexibility in Mu operator DNA was demonstrated by an unusual supercoil-induced DNA conformation, which was detectable by chemical modification with bromoacetaldehyde or digestion with P1 nuclease [15].
  • The transition has been characterized by 2 dimensional gel electrophoresis, mapping of S1, P1 and T7 endonuclease 1 sensitive sites, and mapping of sites that are sensitive to modification by bromoacetaldehyde [16].
 

Analytical, diagnostic and therapeutic context of BRN 0969223

References

  1. Fluorescence study of secondary structure of DNA within bacteriophage lambda. Shurdov, M.A., Kiyanov, S.V. FEBS Lett. (1983) [Pubmed]
  2. Chromatin structure and induction-dependent conformational changes of human interferon-beta genes in a mouse host cell. Bode, J., Pucher, H.J., Maass, K. Eur. J. Biochem. (1986) [Pubmed]
  3. Poly(dG)-poly(dC) sequences, under torsional stress, induce an altered DNA conformation upon neighboring DNA sequences. Kohwi-Shigematsu, T., Kohwi, Y. Cell (1985) [Pubmed]
  4. Initiation of rolling-circle replication in pT181 plasmid: initiator protein enhances cruciform extrusion at the origin. Noirot, P., Bargonetti, J., Novick, R.P. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  5. Detection of an altered DNA conformation at specific sites in chromatin and supercoiled DNA. Kohwi-Shigematsu, T., Gelinas, R., Weintraub, H. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  6. Roles of 2-haloethylene oxides and 2-haloacetaldehydes derived from vinyl bromide and vinyl chloride in irreversible binding to protein and DNA. Guengerich, F.P., Mason, P.S., Stott, W.T., Fox, T.R., Watanabe, P.G. Cancer Res. (1981) [Pubmed]
  7. Persistence of DNA synthesis arrest sites in the presence of T4 DNA polymerase and T4 gene 32, 44, 45 and 62 DNA polymerase accessory proteins. Charette, M.F., Weaver, D.T., DePamphilis, M.L. Nucleic Acids Res. (1986) [Pubmed]
  8. Unusual DNA structure in the regulatory region of the human papovavirus JC virus. Amirhaeri, S., Wohlrab, F., Major, E.O., Wells, R.D. J. Virol. (1988) [Pubmed]
  9. Analysis of DNA structure in the human insulin gene-linked polymorphic region in vivo. Hammond-Kosack, M.C., Kilpatrick, M.W., Docherty, K. J. Mol. Endocrinol. (1992) [Pubmed]
  10. Inter-individual variability in the oxidation of 1,2-dibromoethane: use of heterologously expressed human cytochrome P450 and human liver microsomes. Wormhoudt, L.W., Ploemen, J.H., de Waziers, I., Commandeur, J.N., Beaune, P.H., van Bladeren, P.J., Vermeulen, N.P. Chem. Biol. Interact. (1996) [Pubmed]
  11. Unusual conformational effect exerted by Z-DNA upon its neighboring sequences. Kohwi-Shigematsu, T., Manes, T., Kohwi, Y. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  12. Characteristics of Z-DNA helices formed by imperfect (purine-pyrimidine) sequences in plasmids. McLean, M.J., Lee, J.W., Wells, R.D. J. Biol. Chem. (1988) [Pubmed]
  13. Ethylene dibromide and disulfiram: studies in vivo and in vitro on the mechanism of the observed synergistic carcinogenic response. Elliott, B.M., Ashby, J. Carcinogenesis (1980) [Pubmed]
  14. Analyses of adenosine and adenine nucleotides in biological materials by fluorescence reaction-high-performance liquid chromatography. Yoshioka, M., Yamada, K., Abu-Zeid, M.M., Fujimori, H., Fuke, A., Hirai, K., Goto, A., Ishii, M., Sugimoto, T., Parvez, H. J. Chromatogr. (1987) [Pubmed]
  15. Supercoiling and integration host factor change the DNA conformation and alter the flow of convergent transcription in phage Mu. Higgins, N.P., Collier, D.A., Kilpatrick, M.W., Krause, H.M. J. Biol. Chem. (1989) [Pubmed]
  16. Transition of a cloned d(AT)n-d(AT)n tract to a cruciform in vivo. Haniford, D.B., Pulleyblank, D.E. Nucleic Acids Res. (1985) [Pubmed]
  17. Fluorometric assay using high-pressure liquid chromatography for the microsomal metabolism of certain substituted aliphatics to 1,N6-ethenoadenine-forming metabolites. Rinkus, S.J., Legator, M.S. Anal. Biochem. (1985) [Pubmed]
 
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