Amine effect on phenylboronic acid compiler with glucose under physiological pH in aqueous solution

A new 'intelligent' polymer system was developed utilizing the binding and exchange of phenylboronic acid (PEA) with polyols and/or glucose. In this improved system, an amine component was incorporated into the polymer chain along with PEA, to enhance binding between PEA and glucose under physiological conditions. The PEA-based polymer was formed by free-radical copolymerization of 3-methacrylamido-phenylboronic acid (MAPB) with comonomers, N,N-dimethylaminopropylacrylamide (DMAPAA) and acrylamide (AAm) in the presence of N,N'-methylenebis(acrylamide) (Bis-AAm) as a cross-linker. The proportion of the amount of PEA groups complexed with glucose vs total amount of PEA groups was determined by the batch method. Compared to PEA copolymers synthesized without amine component, the proportion increased as a function of the amine content as well as the pH of the buffer. These results confirm that the interaction of neighboring amines (unprotonated) to PEA strengthens the binding with glucose, especially at pH 7.4 and above. This new PBA-amine copolymer is promising as a material useful for polyol separation, protection of polyols, and possibly, as an insulin delivery device.