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

The formation of inclusion complexes of the water-soluble -sulfonatocalix[ ]arenes, where = 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 se...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2018-01, Vol.23 (1), p.207
Main Authors: Ede, Jayne A, Cragg, Peter J, Sambrook, Mark R
Format: Article
Language:English
Subjects:
Affinity
Aromatic compounds
Biological & chemical weapons
Calixarenes
Chemical warfare
chemical warfare agent
Complementarity
Complex formation
complexation
computational
hydrophobic effect
Hydrophobicity
inclusion complex
Inclusion complexes
nerve agent
Stoichiometry
supramolecular
Water chemistry
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Summary:The formation of inclusion complexes of the water-soluble -sulfonatocalix[ ]arenes, where = 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 ( < 100 M ) 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23010207