Encapsulation-release property of amphiphilic hyperbranched D-glucan as a unimolecular reverse micelle

The synthesis of a novel unimolecular reverse micelle, the hyperbranched D-glucan carbamate (3), was accomplished through the carbamation reaction of the hyperbranched D-glucan (1) with the N-carbonyl L-leucine ethyl ester (2) in pyridine at 100 degrees C. Polymer 3 was soluble in a large variety of organic solvents, such as methanol, acetone, chloroform, and ethyl acetate, and insoluble in water, which remarkably differed from the solubility of 1. The degree of carbamate substitution (DS) for 3 was controlled by the feed rate of 2, and the DS values were in the range of 46.0-93.7%. Polymer 3 possessed the encapsulation ability for water-soluble molecules, such as rose bengal, thymol blue, and alizarin yellow in chloroform, and the encapsulation ability depended on the hydrophilicity of 3 and the molecular size of the dye. The rose bengal (RB) encapsulated polymer (RB/3) showed a slow release from the RB/3 system into water at neutral pH, while the release rate was significantly accelerated by the hydrolysis of the hydrophobic polymer shell under basic conditions. (c) 2007 Elsevier Ltd. All rights reserved.