2016
DOI: 10.1371/journal.pone.0154339
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Interactions of Indole Derivatives with β-Cyclodextrin: A Quantitative Structure-Property Relationship Study

Abstract: Retention factors for 31 indole derivatives, most of them with auxin activity, were determined by high-performance liquid chromatography, using bonded β-cyclodextrin as a stationary phase. A three-parameter QSPR (quantitative structure-property relationship) model, based on physico-chemical and structural descriptors was derived, which accounted for about 98% variations in the retention factors. The model suggests that the indole nucleus occupies the relatively apolar cavity of β-cyclodextrin while the carboxy… Show more

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Cited by 8 publications
(3 citation statements)
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“…This compound forms a pore, where the inner side is hydrophobic while the exterior is hydrophilic. A strong interaction between indoles and β-cyclodextrin has been demonstrated, showing promise for their incorporation to tailor the selectivity of colorimetric devices [ 27 ]. When CD was incorporated in the sensing mixture along with chromogenic dyes, the average signal response to indoles increased by 195%.…”
Section: Resultsmentioning
confidence: 99%
“…This compound forms a pore, where the inner side is hydrophobic while the exterior is hydrophilic. A strong interaction between indoles and β-cyclodextrin has been demonstrated, showing promise for their incorporation to tailor the selectivity of colorimetric devices [ 27 ]. When CD was incorporated in the sensing mixture along with chromogenic dyes, the average signal response to indoles increased by 195%.…”
Section: Resultsmentioning
confidence: 99%
“…CDs can form complexes with a wide range of molecules, including alkyl glycosides [125][126][127], chiral compounds [128][129][130][131][132][133], branched or cyclic alkyl groups [134,135], aromatic molecules [130,136,137], and proteins [138][139][140][141]. Interactions between cyclodextrins (host) and guest molecules may yield a stable complex with a high equilibrium constant; for example, β-CD forms a highly stable inclusion complexes with adamantyl derivatives with a binding constant of ~10 4 -10 5 M −1 [142,143] (See Table 6 for more examples).…”
Section: Introductionmentioning
confidence: 99%
“…Among the functional materials, β-Cyclodextrin (β-CD) has attracted particular attention, due to its unique availability, physic-chemical characteteristics and low cost [12]. The central cavity of cyclodextrins, which is lined with methylene hydrogens and glycosidic oxygen bridges, is relatively hydrophobic compared to water [13].…”
Section: Introductionmentioning
confidence: 99%