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Interaction of soman with beta-cyclodextrin.

B Desire, S Saint-Andre

    Fundamental and Applied Toxicology : Official Journal of the Society of Toxicology
    |November 1, 1986
    PubMed
    Summary
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    Beta-cyclodextrin effectively inactivates the neurotoxic agent soman (pinacolyl methylphosphonofluoridate) by forming a 1:1 complex. This interaction significantly accelerates soman hydrolysis, suggesting potential for modified cyclodextrins in detoxification.

    Area of Science:

    • Biochemistry
    • Chemical kinetics
    • Toxicology

    Background:

    • Neurotoxic agents like soman pose significant health risks.
    • Beta-cyclodextrin is a cyclic oligosaccharide with potential applications in detoxification.
    • Understanding the interaction between neurotoxins and cyclodextrins is crucial for developing effective countermeasures.

    Purpose of the Study:

    • To investigate the inactivation of soman by beta-cyclodextrin.
    • To elucidate the kinetics and mechanism of the interaction between soman and beta-cyclodextrin.
    • To explore the potential of modified beta-cyclodextrins for enhanced soman detoxification.

    Main Methods:

    • Soman inactivation by beta-cyclodextrin was studied at pH 7.40 and 25°C.
    • Acetylcholinesterase (AChE) inhibition was used to monitor soman interaction.

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  • Fluoride ion release was continuously titrated using a fluoride-specific electrode.

    • Main Results:

    • Beta-cyclodextrin significantly inactivated soman, forming a 1:1 complex with a dissociation constant (Kd) of 0.53 ± 0.05 mM.
    • The rate constant for soman cleavage by beta-cyclodextrin (k2) was 5.9 ± 0.6 x 10⁻² min⁻¹.
    • Monoionized beta-cyclodextrin hydrolyzed soman approximately 2500 times faster than hydroxide ions, with stereospecificity observed for P(-)-isomers.

    Conclusions:

    • Beta-cyclodextrin effectively inactivates soman through complexation and hydrolysis.
    • The rate of soman inactivation by beta-cyclodextrin in human plasma was comparable to that in buffer solutions.
    • Modification of beta-cyclodextrin could potentially enhance its catalytic efficiency for soman detoxification.