We have shown that radical-mediated thiol-ene chemistry provides a robust and simple platform for amorphous polyanhydride synthesis, and that the cross-linked products have low moduli of elasticity and degrade quickly (a 1 cm<sup>3</sup> cube degrades within a few days), although the erosion kinetics of these materials are non-linear and appear more complicated than other surface-eroding materials. In comparison with traditional approaches to polyanhydride synthesis that are based on polycondensations, radical polymerization approaches have many advantages, a primary one being that various monomers are simple and readily available. Conventional radical polymerization of methacrylates and vinyl monomers are widely practiced and is the method of choice for the production for many commodity plastic materials. Radical-mediated thiol-ene/yne polymerizations of polyanhydrides also have low susceptibility to oxygen, low shrinkage, and uniform cross-link density and because thiol-ene/yne polymerization occurs via a step-growth mechanism, the degradable anhydride functionality resides in the main chain, rather than a side chain, which reduces the molecular weight of the degradation products compared to materials synthesized by chain growth polymerizations. From an application point of view, our studies indicate that drug delivery from polyanhydrides is typically dictated by erosion kinetics rather than diffusion. We have also shown that these polyanhydrides have low toxicity towards several cell types, and therefore are good options for therapeutic release devices.

Polyanhydrides from radical-mediated thiol-ene polymerizations: From synthesis to drug delivery

2019 Spring National Meeting

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