title: 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.
authors.affiliation: The Group of Biomaterials and Nanotechnology for Improved Medicines (BIONIMED), Department of Pharmaceutical Technology, Faculty of Pharmacy and Biochemistry, University of Buenos Aires, Buenos Aires, CP1113, Argentina; National Science Research Council (CONICET), Buenos Aires, Argentina.
authors.forename: Romina J
authors.initials: RJ
authors.lastname: Glisoni
authors.forename: Alejandro
authors.initials: A
authors.lastname: Sosnik
mesh_terms: D000371:Agglutination; D002152:Calorimetry, Differential Scanning; D003208:Concanavalin A; D000069454:Darunavir; D005942:Gluconates / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D005965:Glucuronates / Q000737:chemistry*; D006031:Glycosylation; D007783:Lactones / Q000737:chemistry*; D008027:Light; D008823:Micelles; D046529:Microscopy, Electron, Transmission; D008872:Microwaves; D008970:Molecular Weight; D010316:Particle Size; D011092:Polyethylene Glycols / Q000737:chemistry*; D011095:Polyethylenes / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D011126:Polypropylenes / Q000737:chemistry; D019946:Propylene Glycol / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D012542:Scattering, Radiation; D012995:Solubility; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D055672:Static Electricity; D013449:Sulfonamides / Q000494:pharmacology; D014867:Water / Q000737:chemistry
chemical_list: D005942:Gluconates; D005965:Glucuronates; D007783:Lactones; D008823:Micelles; D011095:Polyethylenes; D011108:Polymers; D011126:Polypropylenes; D011409:Propylene Glycols; D013449:Sulfonamides; D014867:Water; D003208:Concanavalin A; C012504:polypropylene glycol; D011092:Polyethylene Glycols; D019946:Propylene Glycol; C078661:UCON 50-HB-5100; D005947:Glucose; C010730:beta-glucono-1,5-lactone; D000069454:Darunavir
keywords: Glucosylated poly(ethylene oxide)-b-poly(propylene oxide) block copolymers; darunavir free base; gluconolactone; microwave-assisted ring opening conjugation; polymeric micelles