Synthesis of glycerolipidyl derivatives of permethylated β-cyclodextrin as potential nanovectors

Abstract

This work reports the chemo-enzymatic synthesis of a new family of amphiphilic cyclodextrins for Nano Drug Delivery. Monoamino-permethylated β-CD 1 was used as the polar head of amphiphilic structures. Three derivatives of glycerol were grafted onto cyclodextrin with or without a spacer arm. The two free hydroxyl groups were submitted to lipase-catalyzed reaction in mild conditions, leading to mono- or diesterified compounds. The reactivity of the hydroxyl groups was discussed and the compounds were fully characterized by NMR and mass spectrometry. The surfactive properties of bicatenar compounds 8, 9, 12 and 14 were evaluated and low CAC were determined, suggesting very promising assembly properties of these compounds in aqueous media.