title: Allylic compounds bind directly to DNA: investigation of the binding mechanisms in vitro.
abstract: 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.
mesh_terms: D000477:Alkylating Agents / Q000378:metabolism*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007700:Kinetics; D008698:Mesylates / Q000378:metabolism
chemical_list: D000477:Alkylating Agents; D000498:Allyl Compounds; D008698:Mesylates; C052010:allyl methanesulfonate; D004247:DNA; C050431:allyl bromide; C023698:allyl chloride