Nucleophilic Reagent Effect on Mutagenic, Chlorinated Drinking Water

摘要

The research reported here concerns the genotoxic, halogenated 2(5H)-furanones, agroup of small molecules among the innumerable formed in the clorination of organic-burdened waters. Water chlorinations are conducted in various industrial processes, such as the pulping of wood or the remediation of waste water, but also in the disinfection of public drinking water from both ground and surface sources. The occurrence of halogenated 2(5H)-furanones is a concern because of the possible long-term carcinogenicity potential from the chronic ingestion of these substances. Our research during the initial period of USGS support (Award 14-08-0001-G1498) concentrated on the question of the relation of mutagenic potency to molecular structure. In pursuit of the structure-activity goal, considerable effort was committed to developing an efficient method of synthesizing chlorine-substituted 2(5H)-furanones. Our research during the initial three-year period of USGS support also touched on the mutagenic inactivation of halogen-substituted 2(5H)-furanones by nucleophiles. Glutathione (GSH) was found the most effective inactivating agent. More recently, the study of nucleophiles has expanded to include the interaction between closed, circular DNA and a pair of chlorine-substituted 2(5H)-furanones. The readily accessible pairs: mucochloric acid, mucobromic acid, reduced mucochloric acid, and reduced mucobromic acid were studied to test the model generated from correlating degree of mutagenicity with structure and computed electrophilicity indicators. The report that follows details the activities introduced in the preceding paragraphs. Achievements are described and significance is noted.