Inclusion complex of n-octyl beta-D-glucopyranoside and alpha-cyclodextrin in aqueous solutions : thermodynamic and structural characterization

Complex formation between octyl beta-D-glucopyranoside (OG) and alpha-cyclodextrin (alphaCD) was investigated on the basis of three highly accurate and appropriate experimental techniques. First, surface tension measurements showed that alphaCD directly acts on the surfactant monomers in the aqueous...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 24(2008), 7 vom: 01. Apr., Seite 3140-9
1. Verfasser: Bernat, Valérie (VerfasserIn)
Weitere Verfasser: Ringard-Lefebvre, Catherine, Bas, Geneviève Le, Perly, Bruno, Djedaïni-Pilard, Florence, Lesieur, Sylviane
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2008
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Glucosides Macromolecular Substances Micelles alpha-Cyclodextrins octyl-beta-D-glucoside 29836-26-8 alpha-cyclodextrin Z1LH97KTRM
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245 1 0 |a Inclusion complex of n-octyl beta-D-glucopyranoside and alpha-cyclodextrin in aqueous solutions  |b thermodynamic and structural characterization 
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500 |a ErratumIn: Langmuir. 2008 Oct 7;24(19):11322 
500 |a Citation Status MEDLINE 
520 |a Complex formation between octyl beta-D-glucopyranoside (OG) and alpha-cyclodextrin (alphaCD) was investigated on the basis of three highly accurate and appropriate experimental techniques. First, surface tension measurements showed that alphaCD directly acts on the surfactant monomers in the aqueous phase, leading to progressive depletion of the air-water interface with increasing cyclodextrin contents. Significant shift of OG critical micelle concentration (cmc) was consequently observed: the higher alphaCD concentration, the higher the cmc value. Experiments performed at surfactant and cyclodextrin concentrations in the Gibbs regime of surface tension versus OG content were performed on one hand to establish Job's plot that showed 1:1 stoichiometry of the OG-alphaCD complex and on the other hand to calculate the association constant found equal to (1.85 +/- 0.35) x 10(3) L mol(-1). An inclusion process of the surfactant alkyl residue within the cyclodextrin cavity was confirmed by one-dimensional (1)H NMR, and the structure of the mixed assembly was extensively characterized by two-dimensional NOESY (1)H NMR. OG penetrates alphaCD so that its hydrocarbon chain is embedded inside the cyclodextrin cavity, and its polar head as well as the alpha-methylene group emerges outside the alphaCD secondary face. Solubility behavior of the OG-alphaCD complex in a wide range of host-guest ratios and concentrations was finally examined by turbidity recording and optical microscopy. At very low free cyclodextrin levels in the solution, the complex presented high solubility behavior up to more than 70 mM. By increasing nonassociated alphaCD in the mixture, propensity of the cyclodextrin molecules to crystallize was observed at concentrations far below the 100 mM aqueous solubility of the pure cyclodextrin. The hexagonal shape of the crystals seen in the optical microscopy images suggested they were, partially at least, composed of the solid complex 
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650 7 |a alpha-Cyclodextrins  |2 NLM 
650 7 |a octyl-beta-D-glucoside  |2 NLM 
650 7 |a 29836-26-8  |2 NLM 
650 7 |a alpha-cyclodextrin  |2 NLM 
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700 1 |a Ringard-Lefebvre, Catherine  |e verfasserin  |4 aut 
700 1 |a Bas, Geneviève Le  |e verfasserin  |4 aut 
700 1 |a Perly, Bruno  |e verfasserin  |4 aut 
700 1 |a Djedaïni-Pilard, Florence  |e verfasserin  |4 aut 
700 1 |a Lesieur, Sylviane  |e verfasserin  |4 aut 
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