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

Jayne A. Ede; Peter Cragg; Mark Sambrook

doi:10.3390/molecules23010207

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

Jayne A. Ede, Peter Cragg, Mark Sambrook

Research output: Contribution to journal › Article › peer-review

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 (K assoc < 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.

Original language	English
Journal	Molecules
Volume	23
Issue number	1
DOIs	https://doi.org/10.3390/molecules23010207
Publication status	Published - 19 Jan 2018

Bibliographical note

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).

Keywords

supramolecular
hydrophobic effect
chemical warfare agent
nerve agent
complexation
inclusion complex
computational

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Peter Cragg
- P.J.Craggbrighton.acuk
- School of Applied Sciences - Prof. in Supramolecular Chemistry
- Applied Chemical Sciences Research Excellence Group
- Centre for Lifelong Health
Person: Academic

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

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 (K assoc < 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.",

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AU - Cragg, Peter

AU - Sambrook, Mark

N1 - 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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N2 - 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 (K assoc < 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.

AB - 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 (K assoc < 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.

KW - supramolecular

KW - hydrophobic effect

KW - chemical warfare agent

KW - nerve agent

KW - complexation

KW - inclusion complex

KW - computational

U2 - 10.3390/molecules23010207

DO - 10.3390/molecules23010207

M3 - Article

SN - 1420-3049

VL - 23

JO - Molecules

JF - Molecules

IS - 1

ER -

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

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Peter Cragg

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