Acridines, such as proflavine, are known DNA intercalators, which makes them extremely useful as chemotherapeutic agents and as probes to understand how DNA-drug interactions occur. Intercalation of these compounds between planar DNA base pairs allows for the unwinding of DNA, causing structural changes to the DNA, which can lead to functional changes, including the inhibition of transcription and replication. These functional changes make DNA intercalators extremely useful in inhibiting replication in cancer cells, leading to their use as potent chemotherapeutic treatments. This project focuses on modifying the structure of proflavine through mostly single-step synthesis, in particular functionalizing the amines, and examining how these changes influence DNA binding. The synthesized compounds will be analyzed for DNA binding and intercalation using various methods. Characterization of prepared compounds will be completed with IR, as well as 1H and 13C NMR. Future experiments will focus on further functionalizing the prepared derivatives and using DNA binding data to synthesize more potent DNA intercalators.

Acridines as DNA intercalators: Synthesis of proflavine derivatives

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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