Sustained release applications of a fluoroalkyl ester-functionalized amphiphilic cyclodextrin by inclusion complex formation with water-soluble drugs in supercritical carbon dioxide

An amphiphilic γ-cyclodextrin, selectively functionalized with perfluorobutanoyl group, octakis(6-O-perfluorobutanoyl)-γ-cyclodextrin (γ-CyD-F), was investigated as a potential sustained release carrier for hydrophilic drugs, taking molsidomine (MOL) as a model drug. Supercritical carbon dioxide, an environmentally benign solvent, was used for the preparation of MOL/γ-CyD-F inclusion complexes. The molecular encapsulation of MOL by the amphiphilic cyclodextrin was confirmed by differential scanning calorimetry (DSC) and powder X-ray diffraction (XRD) studies. Additionally, 1H NMR spectroscopy was used to investigate the inclusion mode of drug with the γ-CyD-F. The in-vitro release of MOL from the peanut oil suspensions into aqueous phase was found to be significantly retarded by the complexation with γ-CyD-F, mainly due to the hydrophobic properties associated with the γ-CyD-F.

Graphical abstractAn amphiphilic cyclodextrin, modified with fluoroalkyl ester groups substituted at the primary rim of the macrocycle, was investigated for its potential use as a controlled release carrier for hydrophilic drugs. Host–guest inclusion complexes were prepared using a “green” solvent supercritical carbon dioxide.Figure optionsDownload full-size imageDownload as PowerPoint slide