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- W2893779501 abstract "Pyridinium aldoximes are best-known as therapeutic antidotes for organophosphorus chemical warfare nerve-agents and pesticides. Polyhalogenated quinones are a class of carcinogenic intermediates and newly identified chlorination disinfection byproducts in drinking water. However, it is not clear what is the exact chemical mechanism underlying such detoxication. Here we showed that pralidoxime, one of the representatives of pyridinium aldoximes, can markedly enhance the dechlorination and hydroxylation of the highly reactive and toxic tetrachloro-1,4-benzoquinone (also called chloranil) in two-consecutive steps to produce the much less toxic 2,5-dichloro-3,6-dihydroxy-1,4-benzoquonine (chloranilic acid), with rate acceleration of up to 180000-times. In contrast, no enhancing effect was observed when the hydroxylamine group was blocked via methylation to form O -methylated pralidoxime. The major reaction product from pralidoxime was characterized as its corresponding nitrile (2-cyano-1-methylpyridinium chloride). Along with oxygen-18 isotope-labeling studies, we proposed that nucleophilic substitution coupled with an unprecedented double Beckmann fragmentation reaction was responsible for this dramatic enhancement of the detoxification reaction. This paper reviewed the unprecedented double Beckmann fragmentation reaction. Our findings may have broad biological and environmental implications for future research on the aldoxime therapeutic agents and carcinogenic polyhalogenated quinones, which are two important classes of compounds of major biomedical and environmental interest." @default.
- W2893779501 created "2018-10-05" @default.
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- W2893779501 date "2018-09-21" @default.
- W2893779501 modified "2023-09-24" @default.
- W2893779501 title "A new detoxification mechanism for aldoxime therapeutic antidotes for chemical warfare nerve-agents" @default.
- W2893779501 doi "https://doi.org/10.1360/n032018-00084" @default.
- W2893779501 hasPublicationYear "2018" @default.
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