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New Polyfunctional Derivatives of ß-Cyclodextrin Suited for the Formulation of Drug Release Systems

Department of Chemistry and Industrial Chemistry University of Pisa via Risorgimento 35 56126, Pisa, Italy

Salvatore D'Antone

Department of Chemistry and Industrial Chemistry University of Pisa via Risorgimento 35 56126, Pisa, Italy

Luca Bemporad

Department of Chemistry and Industrial Chemistry University of Pisa via Risorgimento 35 56126, Pisa, Italy

Emo Chiellini

Department of Chemistry and Industrial Chemistry University of Pisa via Risorgimento 35 56126, Pisa, Italy

New functional derivatives of ß-cyclodextrin were obtained by grafting ß-cyclodextrin with epoxides of protected polyols, such as glycidyliso propylideneglycerol, glycidyldiisopropylidenexylitol and glycidyldiisopropyl idenearabitol. The glycidyl ether of 2-pyrrolidone was also used. The reaction products have a degree of substitution per glucose residue included between 0.5 and 1. Selective removal of protecting groups from cyclodextrin substituents, carried out under conditions not affecting the integrity of the cyclodextrin ring, gave rise to hydrosoluble cyclodextrin derivatives whose hydrophilic/hydropho bic balance was modulated by controlling the extent of deprotection. The un usual solubility in water, greater than 350%, for both protected and depro tected derivatives, represents a breakthrough for a wide variety of applications requiring polymeric materials with remarkable water solubility.

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