Aliphatic polycarbonates are an important class of biocompatible and biodegradable materials widely used for drug delivery and tissue engineering applications. The growing need for increasingly versatile biomaterials has spurred the development of functional polycarbonates, to enable facile tuning of their physicochemical and biological properties by installation of sites for covalent conjugation. We report on the synthesis of copolymers of poly(ethylene glycol) (PEG) and a polycarbonate containing pendant boronic acids, to enable dynamic-covalent chemistry at the hydrophobic block. The organocatalytic polymerization of 5-methyl-5-(phenylboronic acid) oxycarbonyl-1,3-trimethylene carbonate, from a PEG macroinitiator, was studied. The functional amphiphilic copolymer that results after deprotection, generates sites for the incorporation of active molecules. We studied the binding affinity between the polymer and the anticancer drug capecitabine, incorporated through the boronic acid pendant group. We studied drug incorporation through Flash Nanoprecipitation, a method based on competitive times of polymer aggregation, drug-polymer conjugation, and drug precipitation. Stimuli-responsive drug release and core-swelling was studied for a range of pH values and in the presence of triggering agents such as hydrogen peroxide. We report differences between particles generated by this method and one where assembly and reaction kinetics do not influence drug loading.

Polycarbonates with pendant boronic acids: Nanoparticles for controlled drug release

247th National Meeting (2014)

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