On the reaction kinetics in water of 1,3-propane sultone and 1,4-butane sultone: a comparison of reaction rates and mutagenic activities of some alkylating agents.
To determine correlations between the biological action pattern and chemical reactivity of alkylating agents, the rate constants for reactions of 1,3-propane sultone and 1,4-butane sultone with a series of nucleophiles at 37 degrees C have been determined. Previously published data on the mutagenicity of the two sultones and of some alkyl methanesulfonates and dialkyl sulfates towards Schizosaccharomyces pombe have been used in the evaluation of the dependence of mutagenic effectiveness on chemical reactivity. It is of interest to note that the mutagenic effectiveness of the two sultones, if expressed per alkylating event at a certain low nucleophilicity is the same as that of e.g. methyl methanesulfonate and ethyl methanesulfonate.
D000476:Alkanesulfonates / Q000494:pharmacology*; D000477:Alkylating Agents / Q000494:pharmacology; D001665:Binding Sites; D006860:Hydrogen Bonding; D007700:Kinetics; D007783:Lactones / Q000494:pharmacology; D008433:Mathematics; D009153:Mutagens; D012568:Schizosaccharomyces / Q000187:drug effects; D013329:Structure-Activity Relationship; D013876:Thiophenes; D014867:Water
D000476:Alkanesulfonates; D000477:Alkylating Agents; D007783:Lactones; D009153:Mutagens; D013876:Thiophenes; D014867:Water; C000335:butanesultone; C003218:1,3-propane sultone