Synthesis of a poly(ester) dendritic β-cyclodextrin derivative by "click" chemistry: Combining the best of two worlds for complexation enhancement.

In spite of the progress in the cyclodextrins chemistry, the synthesis of monodisperse derivatives with a defined degree of substitution is still a challenge. In this work we present a novel dendritic material produced by combining βCD and second generation poly(ester) dendrons. The selective attachment of dendrons in the seven positions of the βCD-primary face was performed through a CuAAC click reaction, which along with a very simple work-up, allowed obtaining the monodisperse material in very high yields. The product showed a great aqueous solubility and an in vitro non-toxic profile. The enhanced complexation potential of the product was evidenced through the formation of an inclusion complex with albendazole, which presented a Kc  = 29636.17 M-1 . In this system, albendazole was 45 times more water-soluble in comparison to the complex albendazole-native βCD. All these features make the dendritic material very attractive for further applications in the formulation and drug delivery fields.