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Binding, Molecular Mechanics, and Thermodynamics of Cyclodextrin Inclusion Complexes with Ketoprofen in Aqueous Medium

1998; Taylor & Francis; Volume: 3; Issue: 3 Linguagem: Inglês

10.3109/10837459809009858

1097-9867

David Díaz, Carolina Marta Escobar Llanos, María Josefa Bernad‐Bernad, Jesōs Gracia Mora,

Protein Interaction Studies and Fluorescence Analysis

The purpose of this work was to study the interaction forces involved in the inclusion processes of ketoprofen with several cyclodextrins and to assess the best cyclodextrin for complexing this anti-inflammatory drug. The behavior of the inclusion complexes of ketoprofen with alpha-, beta-, and gamma-cyclodextrins was studied by UV-VIS direct spectroscopy, 1H NMR, and molecular mechanics. Thermodynamic parameters for the binding processes were obtained from the temperature variations in binding constants, which manifest that "nonclassical" hydrophobic interactions are the main forces involved in these inclusion processes. Binding constants show that beta- and gamma-cyclodextrins form more stable 1:1 complexes with ketoprofen than does alpha-cyclodextrin. 1H NMR spectra show that the inclusion degree depends on the size of the internal diameter of cyclodextrin. The geometries calculated on the bases of molecular mechanics for these three-dimensional models indicate high stability.