Antiretroviral therapy for treatment of human immunodeficiency virus (HIV) has developed with great success over the last few decades. While the current therapies are successful, patients often meet with severe side effects and the mutagenic nature of the HIV virus leads to a constant need for new drug development. One such method of development involves incorporation of bases that exist in multiple tautomeric forms and thus containing ambiguous hydrogen bonding faces. We have synthesized a set of cytosine-based nucleosides with such characteristics, which, when incorporated into the viral DNA, lead to destabilization of the DNA. When combined with the high error rate of the RNA polymerase enzymes of the HIV virus, such incorporation may lead to an error catastrophe thus resulting in collapse of the virus. Presented here are the results of the synthesis and initial work on the thermal denaturation of DNA duplexes containing the ambiguous nucleosides.

Design of tautomerically ambiguous cytosine-based nucleosides as potential anti-HIV agents

249th National Meeting (2015)

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