Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis
DNA alkylation by the haloethylnitrosoureas: Nature of modifications produced and their enzymatic repair or removal
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2021, International Journal of PharmaceuticsCitation Excerpt :The (2-Chloroethyl)Ethylamino moiety forms a reactive carbonium ion which binds itself to a nucleophilic site. The nitrogen N7 of guanine having the highest electrophilic potential of the DNA, is the main target of the alkylation (Bodell, 2009; Bodell et al., 2007; Ludlum, 1990). Indeed, the O6-guanine, N3-adenine, N2 -guanine, N3 guanine and N7-adenine exhibit lower potentials (Kumar et al., 2004; Pullman and Pullman, 1981).
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Chloroethylating nitrosoureas in cancer therapy: DNA damage, repair and cell death signaling
2017, Biochimica et Biophysica Acta - Reviews on CancerCitation Excerpt :An important nucleophilic site on DNA is the O6-position of guanine, where O6-ClEtG and O6-hydroxy-ethylguanine (O6-OHEtG) are formed. O6-ClEtG is an unstable DNA adduct, which hydrolyses in aqueous solution to N1-hydroxy-ethylguanine (N1-OHEtG) or, in organic solution, to N2-ethanoguanine [5]. Through an intramolecular rearrangement, the unstable O6-ClEtG forms N1-O6-ethanoguanine that binds covalently to a cytosine of the complementary DNA strand and generates a stable DNA lesion, the N1-guanine-N3-cytosine ICL [6–8] (Fig. 2).