This study is devoted to developing amphiphilic, random glycopolymers based on phenylboronic acid, which self-assemble to form nanoparticles (NPs), as a glucose-sensitive agent. Maleimide-glucosamine was copolymerized with 3-acryl aminophenylboronic acid in methanol at 70 degrees C. Using the nanoprecipitation method, NPs with a narrow size distribution were successfully generated. Transmission electron microscopic analysis showed that the NPs were well dispersed as individual, spherically shaped particles. The swelling behavior of the NPs and the in vitro release profiles of insulin at different glucose concentrations revealed definite glucose sensitivity of the glycopolymers. Further, circular dichroism spectroscopy demonstrated that the overall tertiary structure of the released insulin was not altered compared with standard insulin. The analysis of relative cell proliferation suggested that the glycopolymer NPs had good biocompatibility. The glycopolymers that responded to changes in the glucose concentration of the surrounding environment are being aimed for use in self-regulated insulin delivery.