<br/>Nucleic acid bases (nucleobases) are nitrogen-containing bases that are linked to a ribose sugar. Adenine, thymine, guanosine and cytidine are all biological nucleobases. The nucleobases can pair to each other through hydrogen bonding according to traditional Watson-Crick base pairing rules. Through the hydrogen-bonding interactions, these nucleobases can form supramolecular structures that include polymers and hydrogels. Hydrogels are crosslinked networks composed of polymers that have the ability to hold water within the spaces between the polymeric chains. Hydrogels provide an abundance of applications within the biomedical field including cartilage repair, tissue engineering, and wound dressings materials. These nucleobases can be employed to make larger supramolecular polymeric structures that exhibit hydrogel properties. This work explains how guanosine and cytidine precursors are synthesized to function as the anchor of the polymer chain. Functionalization of the 2’ and 3’ position of the nucleobase ribose sugar allows for solubility changes, while functionalization of the 5’ position of the ribose allows for polymer attachment through RAFT polymerization. Here, the synthesis of cytidine precursors to acrylates, vinyl esters, and acrylamides are reported. Once the cytidine precursors on the 5’ position are synthesized, polymerization with the respective acrylate, vinyl ester, and acrylamide precursors can be further explored.  By studying the role of hydrogen-bonding and utilizing nucleobase pairing with the guanosine counterparts, supramolecular polymers and hydrogel drug delivery systems can be designed and synthesized thus resulting in biologically relevant polymers exhibiting both supramolecular and covalent properties.<br/>

Development and synthesis of supramolecular polymers utilizing nucleobase interactions: Synthesis of cytidine polymer precursors

251st National Meeting (2016)

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