Allylic compounds bind directly to DNA: investigation of the binding mechanisms in vitro

The in vitro binding of three allyl compounds, allyl methanesulphonate, allyl bromide and allyl chloride to DNA from salmon sperm was investigated. Kinetic DNA-alkylation measurements revealed significant differences between the strongly alkylating allyl methanesulphonate and allyl bromide with half-life values of 1.5 h and 8.1 h, respectively and the weakly alkylating allyl chloride with a half-life value of 360 h. Five alkylated nucleic bases, 3-allyladenine, N6-allyladenine, N2-allylguanine, 7-allylguanine and O6-allylguanine, could be identified after DNA-alkylation with all three allyl compounds.