A rapid and efficient approach will be presented for the preparation of a versatile class of biocompatible and fully degradable functional polymer nanomaterials derived from renewable resources. Well-defined poly(L-lactide)-block-poly(D-glucose carbonate) (PLLA-b-PDGC) micelles with zwitterionic surface characteristics were constructed using a quick and efficient organocatalyzed one-pot ring opening polymerization (ROP) of L-lactide and alkyne-substituted D-glucose carbonate, followed by click-type thiol-yne reaction with L-cysteine to render the PDGC block hydrophilic. PLLA-b-PDGC-cysteine underwent crystallization-driven self-assembly (CDSA) upon incubation in nanopure water at 65 °C into spherical and cylindrical micelles, of which the morphology was dictated by the hydrophilic/hydrophobic ratio in the block copolymer, as seen by transmission electron microscopy (TEM) and atomic force microscopy (AFM). The stability of the micelles and the hydrolytic degradability of the polymer backbone and side chains were assessed by 1H NMR spectroscopy in aqueous solution at pH 1.0, 7.4 and 10.0 at 37 °C. Electrospray ionization (ESI), and matrix-assisted laser desorption/ionization mass spectrometry (MALDI) were used to identify the hydrolytic degradation products of the copolymers. These functional, fully degradable and biocompatible polymeric nanoparticles hold great promise as carriers for antimicrobial agents or chemotherapeutics.

Rapid and versatile construction of functional amphiphilic cylindrical nanostructures from poly(L-lactide)-block-poly(D-glucose carbonate)s

254th National Meeting (2017)

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