Poly(D-glucose carbonate)s (PGCs) are derived from renewable sources and have the degradation capability into natural byproducts, therefore, they have shown great potential for next-generation biomaterials. However, the lack of functionality that allows for facile and versatile post-polymerization modifications limits the applications of initially-studied PGCs. In this presentation, we report the design, synthesis, and utilization of an alkyne-functionalized D-glucose monomer to construct novel PGC block copolymers. By performing sequential ring-opening polymerizations (ROPs) of D-glucose-based bicyclic carbonate monomers with and without alkynes, well-defined diblock PGC s (PDI &lt; 1.10) bearing pendant alkyne functionalities in a block manner were synthesized and employed for practical and efficient functionalizations through click chemistry. The kinetics of organocatalyzed sequential ROPs were evaluated and both polymerizations exhibited a linear relationship between the monomer conversion and the polymer molecular weight, which confirmed the controlled fashion during each process. Two classic “click” reactions, <i>i.e.</i>, azide-alkyne Huisgen cycloaddition and thiol-yne addition reactions, were employed to render the alkyne-containing block hydrophilic and provide a variety of amphiphilic diblock PGCs, which could be assembled into a family of nanostructures with different sizes, morphologies, surface charges and functionalities, while maintaining alkynes in the hydrophilic domains for further chemical manipulations, <i>e.g.</i>, covalent crosslinking. The micelles and the corresponding shell crosslinked nanoparticles (SCKs) from non-ionic polyethylene glycol (PEG) modified diblock copolymer precursors showed low cytotoxicity toward OVCAR cells, RAW 264.7 mouse macrophage cells, and SJSA cells, making these nanomaterials of interest for biomedical applications. The synthesis, characterization and degradation of these materials will be discussed, with an emphasis toward specific biomedical target applications.

Development of functionalizable and biodegradable poly(D-glucose carbonate)s as emerging nanomaterials toward biomedical applications

251st National Meeting (2016)

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