Design and Applications of Biodegradable and Photoresponsive Polymers Based on Alkoxyphenacyl and Coumarin Moieties

摘要

Photoresponsive materials have unique properties which makes them attractive for biomedical applications such as targeted drug delivery and micropatterned devices. This dissertation utilized a unique approach for incorporation of photoresponsive moieties, alkoxyphenacyl or coumarin chromophores within polymer backbone to synthesize photodegradable polycarbonates, and polyesters. The alkoxyphenacyl polycarbonates showed efficient chain scission upon irradiation at 300 nm as evidenced by 1H NMR, SEC, and UV-Vis spectroscopy. The biocompatibility and biodegradability of photoresponsive alkoxyphenacyl based polycarbonates enables the development of nanoparticles and microfilms, encapsulated with drugs, which in turn can be used as a platform for drug delivery applications. In similar approach, coumarin polyesters showed chain scission upon irradiation at 254 nm and crosslinked upon irradiation at 350 nm as evidenced by 1H NMR, SEC, ATR-IR, and UV-Vis spectroscopy. The properties of the polymers were modulated by the functional groups or the co-monomers used in the polymerization. Biocompatibility and biodegradability of photoresponsive coumarin based polyesters enables the development of micropatterned device as a nerve guidance conduit. Additionally, antimicrobial coatings synthesized from cationic coumarin polyesters showed high efficacy towards inhibiting Pseudomonas aeruginosa attachment and biofilm formation, without significant cytotoxicity. These features make coumarin polyesters attractive candidates for applications such as antimicrobial coatings for implants or medical devices.