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Issue 22, 2014
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Cyclodextrin ion channels

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Seventeen derivatives of α- and β-cyclodextrins were prepared from the cyclodextrin per-6-azide by “click” cyclization with terminal alkynes. Sixteen of these “half-channel” compounds showed significant activity as ion channels in planar bilayer members as assessed by the voltage-clamp technique. Activity ranged from persistent square-top openings to highly erratic conductance; mixed behaviours were evident in virtually all data recorded. Some of the erratic behaviours were shown to follow an apparent power-law distribution of open duration times. The activities observed for the suite were summarized using a model-free activity grid method which displays conductance, duration, and opening behaviour. The overall activity shows the clustering of conductance–duration indicating that activity arises from system properties rather that solely as a property of the compound. The activity grids also support an analysis of structure–activity relationships as they apply to the global behaviour of the compounds and reveal the complexity of a single structure change in controlling the distribution of concurrent conductance behaviours. Transient blockage of channel activity by the hydrophobic guest of the cyclodextrin (1-adamantyl carboxylate) is consistent with the formation of an end-to-end dimer channel among several other competing and interconverting structures.

Graphical abstract: Cyclodextrin ion channels

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The article was received on 03 Mar 2014, accepted on 08 Apr 2014 and first published on 09 Apr 2014

Article type: Paper
DOI: 10.1039/C4OB00480A
Citation: Org. Biomol. Chem., 2014,12, 3622-3634
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    Cyclodextrin ion channels

    J. K. W. Chui and T. M. Fyles, Org. Biomol. Chem., 2014, 12, 3622
    DOI: 10.1039/C4OB00480A

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