Novel poly(ethylene oxide)-b-poly(propylene oxide) copolymer-glucose conjugate by the microwave-assisted ring opening of a sugar lactone

Abstract

In this work, we investigated for the first time the conjugation of gluconolactone to a poly(ethylene oxide)-poly(propylene oxide) block copolymer by a microwave-assisted ring opening reaction. The glucosylated copolymer was obtained with high yield (90%). A conjugation extent of approximately 100% was achieved within 15 min. The modification reduced the critical micellar concentration and increased the size of the micelles. The agglutination of the modified polymeric micelles by a soluble lectin that binds glucose confirmed the recognizability of the modified nanocarrier. Finally, the solubilization of darunavir, an anti-HIV protease inhibitor, showed a sharp increase of the aqueous solubility from 91 microgram/mL to 14.2 and 18.9 mg/mL for 10% w/v pristine and glucosylated polymeric micelles, respectively.

Keywords: Glucosylated poly(ethylene oxide)-b-poly(propylene oxide) block copolymers; darunavir free base; gluconolactone; microwave-assisted ring opening conjugation; polymeric micelles.