PMID: 3771627Jan 1, 1986Paper

DNA adducts of halogenated hydrocarbons

Journal of Cancer Research and Clinical Oncology
H M BoltH Ottenwälder

Abstract

Although formation of DNA adducts has been postulated for several halomethanes, no chemical identification of such adducts has been performed so far. There is, however, evidence that methyl chloride does not act biologically as a DNA methylating agent. 1,2-Dichloroethane and 1,2-dibromoethane are activated through conjugation with glutathione. There is some evidence for formation on an N-7 adduct of guanine which carries an ethyl-S-cysteinyl moiety. Extensive work has been published on adducts of vinyl chloride, both in vitro and in vivo. The major DNA adduct is 7-(2-oxoethyl)guanine; a minor adduct appears to be N2,3-ethenoguanine. Other "etheno" adducts, i.e., 1,N6-ethenoadenine and 3,N4-ethenocytosine, are readily formed with DNA, vinyl chloride, and a metabolizing system in vitro and with RNA in vivo, but are usually not detected as DNA adducts in vivo. The data on DNA alkylation by vinyl chloride (and vinyl bromide) metabolites are compared with those of structurally related compounds (acrylonitrile, vinyl acetate, vinyl carbamate).

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Citations

Apr 3, 2013·Journal of the American Chemical Society·Vinod Kumar, Eric V Anslyn
Mar 22, 2014·Chemical Research in Toxicology·Sergio ManzettiDavid van der Spoel
Jan 1, 1991·Chemico-biological Interactions·J H van DelftR A Baan
Sep 12, 2009·Chemistry : a European Journal·Carmit Hertzog-RonenYoav Eichen
Apr 7, 2006·Chemistry : a European Journal·Shay TalYoav Eichen
Jun 23, 1993·Annals of the New York Academy of Sciences·H YamaguchiY Tokuda
Jul 6, 2010·Chemical Communications : Chem Comm·Wenbo ChenJohn S Fossey

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