“It was the perfect recipe for convincing a synthetic chemist to get into the game. It seemed like there was so much to be discovered,” said K.C. Nicolaou, who holds the titles chair of the Department of Chemistry. Nicolaou’s preferred method is to start with natural products and then modify them in a variety of ways to create new synthetic products with improved potential.
Nicolaou’s team found that the plant could induce formation of critical bonds that join the two domains of the molecules by bombarding the right chemical building blocks with ultraviolet light. This technique, known as photocycloaddition, allowed the scientists to synthesize the two known biyouyanagins as well as a third type not yet discovered in nature. The team then built a library of about 50 analogs using the photocycloaddition.
One compound from the new library, number 53, stood out. In the HIV testing, it compared favorably with the well-known AIDS drug AZT, though it is not yet as potent. In the anti-inflammatory tests, it was as potent or more so than commercially available products. “We were certainly excited to see those results. It’s quite a promising lead.” Next, the team will tinker with 53’s initial structure in search of modifications that will increase its potency. Once its biomedical activities are optimized, the group will consider pushing the compound toward the drug-testing process,” he said. The study will appear in the online Early Edition of Proceedings of the National Academy of Sciences this week. (ANI)
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