Supramolecular azasugar clusters based on an amphiphilic fatty-acid-deoxynojirimycin derivative as multivalent glycosidase inhibitors

Abstract

A novel supramolecular multivalent glycosidase inhibitor was constructed based on the amphiphilic deoxynojirimycin derivative FA-DNJ. FA-DNJ self-assembled into spherical assemblies with the diameters between 103 nm and 137 nm under different pH values (pH 2–7) and showed a potent glycosidase effect against α-mannosidase with a K_i value of 0.11 μM, an effect that increased approximately 330-fold compared with that of miglitol. In addition, FA-DNJ exhibited a hypoglycaemic effect in mice.