Project Team
Students
Shannon Adams
Chemical Engineering
Penn State Erie
Faculty Mentors
Todd Eckroat
Penn State Erie
Chemistry
Scott Medina
Penn State University Park
Biomedical Engineering
Project
https://sites.psu.edu/mcreu/files/formidable/2/Lab-Poster-Final-PDF.pdf
Project Video
Project Abstract
In the United States alone, approximately 1.6 million people are diagnosed and up to 600,000 die from cancer each year. Cancers tend to develop drug resistances over time, so the more anti-cancer drugs available, the better chance doctors have at combating them. Orycophragine A is a recently isolated natural product that has demonstrated cytotoxicity to cancer cells. It is also suspected that it has potential for the inhibition of acetylcholinesterase (AChE), which is an enzyme that controls neurotransmission for learning and memory in the brain, and is an important target for treatment of Alzheimer’s disease. The only problem is that orycophragine A has only ever been derived from its natural resource, the seeds of Orychophragmus Violaceus. The goal of this research project was to find a way to synthetically make this molecule. The original hypothesized synthesis was more difficult than previously expected, with one of the major difficulties being the peptide coupling of an oxalic acid derivative to other pieces. To combat this, multiple protecting groups were used to control the activity at each functional group. Three major routes with different protecting groups were attempted in this project, and while the peptide coupling was unsuccessful, a tri-protected molecule that could be a useful synthetic intermediate for both orychophragine A and other natural products was successfully synthesized. The next step in this research would be to attempt alternate synthetic routes. Once synthesized, it could be tested against cancer cell lines and for AChE inhibition.
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