Our research is designed to utilize hydrogen bonding motifs in guanosine and cytidine nucleobase pairings to assemble drug delivery hydrogels and functional supramolecular polymers. In order to develop an effective drug delivery system to fight cancer cells, delivery systems must have two things: biocompatibility and a high magnitude of packed molecules. We achieve this by using a biocompatible molecule known as Guanosine, which forms quadruplexes. Quadraplexes are comprised of tightly packed molecules of guanosine in the form of quartets that are vertically stacked. These higher order structures are capable of forming hydrogels in sodium and potassium solutions. To develop stable hydrogels, the 8-position must be modified. Cancer cell targeting groups are added to the 5’-position. To this end, we have functionalized the 8-position with small aromatic rings, which stabilize quadraplexes. We have also successfully functionalized the 5’-position with carboxylic acids and amines to append various polyamines to target cancer cells.<br/><br/>With these successful modifications to guanosine, it can also be envisioned that the 5’-position can be adjusted to synthesize supramolecular polymer precursors. To accomplish this, guanosine can be appended with vinyl ester, acrylate, azide, and acrylamide derivatives at the 5’-position. These derivatives will be attached to a larger polymer backbone. The supramolecular polymers are formed via the base pairing of the guanosine and cytidine precursors synthesized in our lab. Both guanosine and cytidine precursors will undergo RAFT polymerization so the size, length, and other physical properties can be controlled. Significant progress has been made in the selective synthesis of the 5’-precursors. Azide precursors have been completed, while the other precursors are one step from completion. In the future, RAFT polymerization will be completed and the guanosine polymers will be paired with cytidine polymers to determine new supramolecular polymeric structures.<br/>

Utilization of nucleobase interactions to develop guanosine hydrogels and supramolecular polymer hybrids

251st National Meeting (2016)

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