Citation

Schneider C, Bierwisch A, Koller M, Worek F, Kubik S. Angew Chem. Int. Ed. Engl. 2016; 55(41): 12668-12672.

Affiliation

Fachbereich Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, 67663, Kaiserslautern, Germany. kubik@chemie.uni-kl.de.

Copyright

(Copyright © 2016, Wiley-VCH)

DOI

10.1002/anie.201606881

PMID

27627873

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.

© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Language: en