concanavalin-a and beta-glucono-1-5-lactone

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.

Topics: Agglutination; Calorimetry, Differential Scanning; Concanavalin A; Darunavir; Gluconates; Glucose; Glucuronates; Glycosylation; Lactones; Light; Micelles; Microscopy, Electron, Transmission; Microwaves; Molecular Weight; Particle Size; Polyethylene Glycols; Polyethylenes; Polymers; Polypropylenes; Propylene Glycol; Propylene Glycols; Proton Magnetic Resonance Spectroscopy; Scattering, Radiation; Solubility; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Spectroscopy, Fourier Transform Infrared; Static Electricity; Sulfonamides; Water