NDLI: Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent

Content Provider	PubMed Central
Author	Zengerle, Michael Brandhuber, Florian Schneider, Christian Worek, Franz Reiter, Georg Kubik, Stefan
Editor	Schalley, Christoph A.
Copyright Year	2011
Abstract	The potential of appropriately substituted cyclodextrins to act as scavengers for neurotoxic organophosphonates under physiological conditions was evaluated. To this end, a series of derivatives containing substituents with an aldoxime or a ketoxime moiety along the narrow opening of the β-cyclodextrin cavity was synthesized, and the ability of these compounds to reduce the inhibitory effect of the neurotoxic organophosphonate cyclosarin on its key target, acetylcholinesterase, was assessed in vitro. All compounds exhibited a larger effect than native β-cyclodextrin, and characteristic differences were noted. These differences in activity were correlated with the structural and electronic parameters of the substituents. In addition, the relatively strong effect of the cyclodextrin derivatives on cyclosarin degradation and, in particular, the observed enantioselectivity are good indications that noncovalent interactions between the cyclodextrin ring and the substrate, presumably involving the inclusion of the cyclohexyl moiety of cyclosarin into the cyclodextrin cavity, contribute to the mode of action. Among the nine compounds investigated, one exhibited remarkable activity, completely preventing acetylcholinesterase inhibition by the (−)-enantiomer of cyclosarin within seconds under the conditions of the assay. Thus, these investigations demonstrate that decoration of cyclodextrins with appropriate substituents represents a promising approach for the development of scavengers able to detoxify highly toxic nerve agents.
Related Links	http://dx.doi.org/10.3762/bjoc.7.182
Ending Page	1554
Page Count	12
Starting Page	1543
File Format	PDF
ISSN	18605397
e-ISSN	18605397
Journal	Beilstein Journal of Organic Chemistry
Volume Number	7
Language	English
Publisher	Beilstein-Institut
Publisher Date	2011-11-01
Access Restriction	Open
Rights Holder	Beilstein-Institut
Subject Keyword	Organic Chemistry Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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