1. Identificationof New DNA Adducts of Phenylnitrenium.
- Author
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Antonín Králík, Igor Linhart, Lubomír Váňa, and Alena Moulisová
- Subjects
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DNA adducts , *NITRENIUM ions , *NUCLEOPHILES , *NITROGEN analysis , *CARBON analysis , *NUCLEOSIDES - Abstract
Phenylnitreniumion (PhNH+) may bind to nucleophiles through nitrogen aswell as through C2 or C4 carbons. However, only adducts of the formertype have been hitherto reported after its reaction with purine nucleosides.In this study, reactions of N-acetoxyaniline (PhNHOAc),a precursor to PhNH+, with 2′-deoxyadenosine (dA),2′-deoxyguanosine (dG), and with DNA in vitroat physiological conditions are described. The reaction of PhNHOAcwith dA followed by a hydrolytic deribosylation afforded 8-phenylaminoadenine(C8-PhNHA) together with a smaller amount of N6-(4-aminophenyl)adenine (N6-4APA). A similar reactionwith dG afforded 8-phenylaminoguanine (C8-PhNHG) together with tracesof 7-(4-aminophenyl)guanine (N7-4APG). The same adducts were foundalso in the DNA treated with PhNHOAc, and all of them were identifiedby comparison of their HPLC retention times and MS2spectrawith a set of synthesized authentic adenine adducts at C2, C8, N7, and N6positions and guanineadducts at C8, N7, and N2positions. The newly identified minor adduct, N7-4APG, representsthe first proof of arylnitrenium adduction at the N7 position of dG, which is the prominent site of attack by most C-electrophiles. [ABSTRACT FROM AUTHOR]
- Published
- 2015
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