Natural products have been the leading source of potential drug leads and comprise approximately a third of the drugs on the market. β-carbolines are a class of naturally occurring, tricyclic aromatic indole alkaloids that have been used to probe the biochemistry of a broad range of ailments. A subclass of β-carbolines, known as the eudistomins, is reported to have diverse biological activity, as well as a high binding affinity to DNA. Through a novel five-step synthesis, our lab successfully synthesized the natural product eudistomin U, a derivative of the eudistomin family. Furthermore, we have characterized eudistomin U’s cytotoxic activity, as well as the compound’s interaction with DNA via spectroscopic and biophysical techniques. We have determined that eudistomin U weakly binds to DNA in a nonspecific fashion, thus DNA binding is most likely not the cause of toxicity observed in the bacterial and cancer cell lines. We hope that future experiments will elucidate how eudistomin U disrupts biochemical pathways.

Synthesis, cytotoxicity, and DNA-binding studies of the natural product eudistomin U

249th National Meeting (2015)

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