Harmful viruses have posed a threat to the human race for generations. In particular, the human immunodeficiency virus (HIV) has been notably damaging to the individual and society alike. Although drugs to treat HIV exist, they are harsh and often result in negative side effects. The low fidelity replication enzymes that the virus replicates with contributes to the relative success of the virus’s ability to evade antiviral medications, but can be exploited to develop new antiviral agents. This research focuses on viral mutagenesis, or the introduction of intentional errors in the genome of the virus. These resulting mutations will lead the DNA to reach error catastrophe and ablate. The method by which error will occur is the assimilation of synthesized cytosine-based nucleosides with ambiguous hydrogen bonding faces resulting from tautomeric shift. These shifts will lead to the mispairing of DNA and a decrease in stability of the duplex molecule. Presented here are the details of the designed nucleosides’ synthesis and spectroscopy, thermal stability of oligomers containing the nucleosides, and biological assays to demonstrate efficacy.

Synthesis and analysis of tautomerically ambiguous cytosine-based analogs to induce viral mutagenesis

253rd National Meeting (2017)

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