The binding behavior of cyclodextrins toward a nitroxide spin probe in the presence of different alcohols as studied by EPR

The Journal of Physical Chemistry. a
Paola FranchiMarco Lucarini

Abstract

Stability constants, rates of association and dissociation, and thermodynamic and activation parameters for the formation of inclusion complexes between the radical guest, N-benzyl- tert-butyl- d 9-nitroxide and beta- or 2,6- O-dimethyl-beta-cyclodextrin (CDs), have been determined by EPR spectroscopy in water in the presence of 14 different alcohols, differing in size and lipophilicity. In all cases, it was found that addition of alcohol, depending on its structure and concentration, causes a reduction of the stability of the paramagnetic complex. Global analysis of EPR data allowed us to explain the CDs binding behavior: we discarded the formation of a ternary complex, where alcohol and radical guest are coincluded into CD cavity, while data were found more consistent with the formation of a binary complex alcohol:CD competing with the monitored complex nitroxide:CD. Both kinetic and thermodynamic analysis of the experimental results have revealed that the presence of alcohols affects to a larger extent the dissociation rather then the association of radical probe and CD and that the former process is of greater importance in determining the stability of the complex, this confirming the reliability of the competition model pr...Continue Reading

References

Oct 1, 1996·Journal of Pharmaceutical Sciences·T Loftsson, M E Brewster
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Feb 19, 2002·Chemical Reviews·Hans-Jörg SchneiderHiroshi Ikeda
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Jun 26, 2007·Chemical Reviews·Reynaldo VillalongaAlex Fragoso

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Citations

Aug 3, 2011·Organic & Biomolecular Chemistry·Paola FranchiMarco Lucarini
Feb 2, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Andrea CantelliMarco Lucarini
May 14, 2010·The Journal of Physical Chemistry. a·Mariana Spulber, Shulamith Schlick
Jun 11, 2020·The Journal of Physical Chemistry. B·James D Nicholas, Victor Chechik

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