Characterization of peracylated β-cyclodextrins with different chain lengths as a novel sustained release carrier for water-soluble drugs

Article abstract of DOI:10.1248/cpb.43.130

A new series of peracylated β-cyclodextrins(β-CyDs) with different alkyl chains (acetyl-lauroyl) was prepared in high purity by acylating all hydroxyl groups of β-CyD using acid anhydrides in pyridine, and their physicochemical properties of solubility, hydrolysis and release and interaction capacity were evaluated. The solubility of peracylated β-CyDs in water decreased with lengthening alkyl chain, whereas that in ethanol/water increased with increase in ethanol concentration, but tended to decrease at higher ethanol concentration. The solubility parameter of peracylated β-CyDs was determined by analyzing the peak-solubility phenomenon by a modified Hildebrand equation. The alkaline hydrolysis rate of peracylated β-CyDs decreased with lengthening alkyl chain, and was about 4-fold faster than that of the corresponding fatty acid ethyl esters. The interaction of perbutanoyl-β-CyD (TB-β-CyD) with a water-soluble drug, molsidomine, in the solid state was investigated by differential scanning calorimetry (DSC). The analysis of DSC curves suggested that molsidomine and TB-β-CyD form a binary solid dispersion with a 2:1 (drug: TB-β-CyD) molar ratio. The rate of drug release was markedly retarded by the combination with peracylated β-CyDs in the increasing order of the hydrophobicity of host molecules.

Full text of DOI:10.1248/cpb.43.130

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