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Detoxification of VX and Other V-Type Nerve Agents in Water at 37 °C and pH 7.4 by Substituted Sulfonatocalix[4]arenes.

ABSTRACT: Sulfonatocalix[4]arenes with an appended hydroxamic acid residue can detoxify VX and related V-type neurotoxic organophosphonates with half-lives down to 3 min in aqueous buffer at 37 °C and pH 7.4. The detoxification activity is attributed to the millimolar affinity of the calixarene moiety for the positively charged organophosphonates in combination with the correct arrangement of the hydroxamic acid group. The reaction involves phosphonylation of the hydroxamic acid followed by a Lossen rearrangement, thus rendering the mode of action stoichiometric rather than catalytic. Nevertheless, these calixarenes are currently the most efficient low-molecular-weight compounds for detoxifying persistent V-type nerve agents under mild conditions. They thus represent lead structures for novel antidotes that allow treatment of poisonings by these highly toxic chemicals.

SUBMITTER: Schneider C

PROVIDER: S-EPMC5113771 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Detoxification of VX and Other V-Type Nerve Agents in Water at 37 °C and pH 7.4 by Substituted Sulfonatocalix[4]arenes.

Schneider Christian C Bierwisch Anne A Koller Marianne M Worek Franz F Kubik Stefan S

Angewandte Chemie (International ed. in English) 20160915 41

Sulfonatocalix[4]arenes with an appended hydroxamic acid residue can detoxify VX and related V-type neurotoxic organophosphonates with half-lives down to 3 min in aqueous buffer at 37 °C and pH 7.4. The detoxification activity is attributed to the millimolar affinity of the calixarene moiety for the positively charged organophosphonates in combination with the correct arrangement of the hydroxamic acid group. The reaction involves phosphonylation of the hydroxamic acid followed by a Lossen rearr ...[more]

PMID: 27627873

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