Biodegradable electroactive materials for tissue engineering applications

This dissertation focuses on the development of biomaterials that could be used to enhance the regeneration of severed peripheral nerves. These materials were designed to be electroactive, biodegradable, and biocompatible. To render the materials electroactive the author chose to incorporate conducting polymer (CP) units into the materials. Because CPs are inherently non-degradable, the key challenge was to create a CP-based material that was also biodegradable. Two strategies were explored to generate a biodegradable CP-based material. The first strategy centered around the incorporation of both electroactive and biodegradable subunits into a copolymer system. In the context of this approach, two bis(methoxyquaterthiophene)-co-adipic acid polyester (QAPE) analogues were successfully synthesized, one through polycondensation (giving undoped QAPE) and the second through oxidative polymerization (giving doped QAPE-2). QAPE was found to be electroactive by cyclic voltammetry, bioerodible, and cytocompatible with Schwann cells. QAPE was doped with ferric perchlorate, although only a low doping percentage was realized (~8%). Oxidative polymerization of a bis(bithiophene) adipate permitted the direct synthesis of doped QAPE-2, which was found to have a higher doping level (~24%). The second strategy pursued with the goal of generating an electroactive biodegradable material involved covalently immobilizing low molecular weight polythiophene chains onto the surface of crosslinked hyaluronic acid (HA) films. HA films are not only biodegradable and biocompatible, but they also provide mechanical integrity to bilayer systems. Dicyclocarbodiimide coupling of carboxylic acids to HA alcohol groups was used to functionalize HA films. The HA-polythiophene composite is still in the early stages of development. However, to date, thiophene has been successfully immobilized at the surface of HA films with a high degree of substitution. The author has also shown that thiophene polymerization can be achieved at the surface of these functionalized films and that the extent of polymer immobilization appears to be affected by the presence of immobilized thiophene. The results reported in this dissertation lead the author to suggest that it is possible to generate biodegradable electroactive materials. Further, she believes that with additional optimization these materials may prove beneficial for the regeneration of peripheral nerves and possibly other tissues that respond favorably to electrical stimulation.