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 journalArticleResearchpeer-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 languageEnglish
JournalMolecules
Volume23
Issue number1
DOIs
Publication statusPublished - 19 Jan 2018

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Calixarenes
Chemical Warfare Agents
Soman
Molecular mechanics
Water
Stoichiometry
Cations
Buffers
Nuclear magnetic resonance
Nerve Agents

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

Cite this

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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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Comparison of Binding Affinities of Water-Soluble Calixarenes with the Organophosphorus Nerve Agent Soman (GD) and Commonly-Used Nerve Agent Simulants. / Ede, Jayne A.; Cragg, Peter; Sambrook, Mark.

In: Molecules, Vol. 23, No. 1, 19.01.2018.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Sambrook, Mark

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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.

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