Advanced molecular design to replace poly(α-hydroxy acid)s in biomedical applications

Advances in biomaterials can be brought about by the development of novel polymers that are designed to satisfy multiple criteria. Some of these criteria are biodegradability, biocompatibility, processability to fabricate into different architectures, and appropriate mechanical properties. Modifying currently existent polymeric biomaterials only gives limited control over desired properties; these properties can be easily tuned when new polymers are designed. One important aspect for the advancement of biomaterials is the ability to functionalize them by attaching biomolecules to create or enhance the regenerative response in the body. While such reactivity is actively being explored in soft polymeric biomaterials such as hydrogels, bioconjugation of biomolecules to stiff polymers has not been investigated. In this dissertation, the synthesis and properties of novel polymers synthesized from naturally occurring molecules such as tyrosol and 2-(4-hydroxyphenyl)acetic acid are reported. The polymers were incorporated with pendant chemical groups that can undergo ‘click’ reactions under physiological conditions. The reactivity of the polymers towards thiol containing small molecule, thiol containing proteins, and proteins and polysaccharides modified with azide group is reported. It was discovered that it is possible to fabricate the designed polymers into computer-aided architectures by fused deposition modeling. Additionally, in this thesis, the structure-property relationship of polycarbonates derived from diesters of 2-(4-hydroxyphenyl)acetic acid and 2-(4-hydroxyphenyl)propionic acid with alkane diols are explored in Chapter 5. The striking difference in thermal and mechanical properties by a small change in the chemical composition of the monomer is noted. Finally, independent research work done on tyrosine-derived polycarbonates is presented in Appendix 1 and 2.Ph.D.Includes bibliographical referencesby Koustubh Shishir Dub