Monosubstituted hydrazone β-cyclodextrin derivatives for pH-sensitive complex formation with aromatic drugs

Abstract

A new and convenient synthetic pathway was developed to produce monosubstituted cyclodextrins with high yields. Each of the β-cyclodextrin derivatives described in this work has an aromatic substituent connected with cyclodextrin core by a pH-sensitive hydrazone linker and a carbon chain. Carbon chains differ in lengths having one or three carbon atoms. The correlation between water solubility and linker length was determined using UV–Vis spectroscopy, while the dependence of hydrazone bond hydrolysis on the electrolyte pH was confirmed by cyclic voltammetry. The pH-dependent complex-formation ability between the hydrazone derivative of cyclodextrin and anthracycline drug was examined by square wave voltammetry. The significantly big solubility and the appropriate pH, at which the hydrolysis of the hydrazone bond occurs, make the newly synthesized derivatives attractive for pharmaceutical and medical applications.