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Molecules 2018, 23(1), 207; https://doi.org/10.3390/molecules23010207

Comparison of Binding Affinities of Water-Soluble Calixarenes with the Organophosphorus Nerve Agent Soman (GD) and Commonly-Used Nerve Agent Simulants

1
CBR Division, Dstl, Porton Down, Salisbury, Wiltshire SP4 0JQ, UK
2
School of Pharmacy and Biomolecular Sciences, University of Brighton, Brighton BN2 4GJ, UK
*
Author to whom correspondence should be addressed.
Received: 9 November 2017 / Revised: 9 January 2018 / Accepted: 14 January 2018 / Published: 19 January 2018
(This article belongs to the Special Issue Calixarenes, Pillararenes, and Cucurbiturils)
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Abstract

The formation of inclusion complexes of the water-soluble p-sulfonatocalix[n]arenes, where n = 4 or 6, with the Chemical Warfare Agent (CWA) GD, or Soman, and commonly used dialkyl methylphosphonate simulants has been studied by experimental solution NMR methods and by Molecular Mechanics (MMFF) and semi-empirical (PM6) calculations. Complex formation in non-buffered and buffered solutions is driven by the hydrophobic effect, and complex stoichiometry determined as 1:1 for all host:guest pairs. Low affinity complexes (Kassoc < 100 M−1) are observed for all guests, attributed to poor host–guest complementarity and the role of buffer cation species accounts for the low affinity of the complexes. Comparison of CWA and simulant behavior adds to understanding of CWA–simulant correlations and the challenges of simulant selection. View Full-Text
Keywords: supramolecular; hydrophobic effect; chemical warfare agent; nerve agent; complexation; inclusion complex; computational supramolecular; hydrophobic effect; chemical warfare agent; nerve agent; complexation; inclusion complex; computational
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Ede, J.A.; Cragg, P.J.; Sambrook, M.R. Comparison of Binding Affinities of Water-Soluble Calixarenes with the Organophosphorus Nerve Agent Soman (GD) and Commonly-Used Nerve Agent Simulants. Molecules 2018, 23, 207.

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