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CC BY 4.0 · Organic Materials 2022; 4(04): 146-152
DOI: 10.1055/a-1939-6455
Supramolecular Chemistry
Short Communication

Characterization of the Interaction of Nerve Agent Mimics with Selected Synthetic Receptors

Carolina Braga Barbosa
a   Fachbereich Chemie – Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. 54, 67663 Kaiserslautern, Germany
,
Patrick Gaß
a   Fachbereich Chemie – Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. 54, 67663 Kaiserslautern, Germany
,
Daniel J. Hamsch
a   Fachbereich Chemie – Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. 54, 67663 Kaiserslautern, Germany
,
Stefan Kubik 
a   Fachbereich Chemie – Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Str. 54, 67663 Kaiserslautern, Germany
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Abstract

Qualitative NMR spectroscopic and quantitative calorimetric binding studies were performed to characterize the interaction of nontoxic mimics of the V-type nerve agent VX (O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothioate) and the Novichok nerve agent A-234 (ethyl (1-(diethylamino)ethylidene)phosphoramidofluoridate) with a series of receptors in 100 mM aqueous phosphate buffer at pH 7.4 and 37 °C. These investigations provided information about the preferred geometry with which the nerve agent mimics are included into the receptor cavities and about the stability of the complexes formed. According to the results, the positively charged VX mimic prefers to bind to cation receptors such as sulfonated calixarenes and an acyclic cucurbituril but does not noticeably interact with cyclodextrins. While binding to the acyclic cucurbituril is stronger than that to calixarenes, the mode of inclusion into the sulfonatocalix[4]arene cavity is better suited for the development of scavengers that bind and detoxify V-type nerve agents. The neutral Novichok mimic, on the other hand, only interacts with the acyclic cucurbituril with a strength required for scavenger development. These binding studies thus provided guidelines for the further development of nerve agent scavengers.

Key words

nerve agents - sulfonatocalixarenes - cyclodextrins - acyclic cucurbiturils - binding studies

Supporting Information



Publication History

Received: 21 July 2022

Accepted after revision: 06 September 2022

Accepted Manuscript online:
08 September 2022

Article published online:
26 October 2022

© 2022. The authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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