Finding the Right Chemistry

MONMOUTH, Ill. – A group of Monmouth College chemistry students are getting the kind of hands-on experience in the laboratory that most college students don’t encounter until graduate school. The three projects – which touch on the topics of medicinal chemistry and Alzheimer’s disease – are being led by chemistry professor Michael Prinsell.

“Performing research as an undergraduate is not common, and I’ve quite enjoyed it,” said Joseph Shie ’21 of Davenport, Iowa. “I’ve loved exploring the unknown and applying the various concepts I’ve learned in my classes to the real world. I’ve learned a lot about problem solving and have been exposed to different laboratory instrumentation, methods and techniques.”

STUDENT RESEARCHERS: Joseph Shie (seated), Brooke Hazelwood and Mamie Ambrosch gather in one of the chemistry labs, along with the professor leading their, Michael Prinsell. Along with Brooke Hazelwood ’20 of Pekin, Illinois, Shie is working on a project that Prinsell was inspired to begin after reading the Journal of Natural Products in graduate school.

“I noticed this paper with interesting molecules that had been discovered that all had nitrogen-nitrogen bonds in the middle,” said Prinsell, when he spoke about his research at a recent faculty colloquium. “If you look into medicinal chemistry, the way that drugs are often discovered is that you use a compound from nature, and then you make small changes that try to change its activity.”

Prinsell referred to an example involving negamycin, where its derivative showed “more potent” antibiotic activity than the negamycin itself.

“I tried to figure out if anyone had done this before (with N-N bonds), and there were very, very limited results out there,” he said. “This is why it’s kind of exciting to try to get a reaction like this to work. If we can, we get molecules that have never been made before.”

Shie plans to pursue dentistry after Monmouth, but he’s still excited about the potential medicinal benefits of his student research.

“I am developing a simpler, more effective approach in the formation of N-N bond containing molecules,” he said. “The potential application for this research is for the pharmaceutical industry to adopt this simpler method. In addition, we would like to determine if any of our formed molecules exhibit biological activity. It is possible that these molecules could be modified or used within the pharmaceutical industry to treat various types of illness.”

Prinsell is also working with Mamie Ambrosch ’20 of Metamora, Illinois, on a project involving Alzheimer’s disease, for which there is no known cure.

“Essentially, we’re investigating simple molecules that could have a beneficial effect on people with Alzheimer’s,” he said.

Ambrosch – who plans to go to medical school – and Prinsell have analyzed 100 derivatives of their “scaffold of choice,” chalcones.

“Analyzing chalcones is something that an undergraduate student can do, using an aldol reaction,” said Prinsell.

Prinsell referred to his third active research area as “separation/characterization.” In the past few years, several students have been part of that project, and it’s currently being explored by Logan Evans ’21 of Glasford, Illinois.

“We separate compounds into pieces and try to figure out what they are,” said Prinsell, casting the project in the simplest terms possible.

“It builds my critical thinking skills, problem-solving skills, data analysis skills, and helps me determine if I would like to pursue research as a career.” - Logan Evans

He also offered a more complex description at the faculty colloquium: “To summarize this project, we separated and isolated some compounds with flash chromatography, verified them with HPLC (high-performance liquid chromatography) after we characterized them with NMR (nuclear magnetic resonance spectroscopy), and we’re trying to get NMRs of each of the purified acids. Then we would like to test the biological properties of these compounds.”

Added Evans: “My research pertains to the separation of certain acids in hops, one of the components in the beer brewing process. I use chromatographic methods to perform these separations, in order to make standards – pure samples – of these acids, which may have medicinal purposes. As of now, no standards are on the market, so having these standards would allow scientists to perform tests and studies on the individual acids, as opposed to all of them at once.”

Shie knows he’ll be taking what he’s learned from his work with Prinsell into his future educational and professional experiences.

“Overall,” said Shie, “this experience broadened my understanding of research, labs and how the scientific community tackles issues and mysteries. Without this opportunity, I would not be nearly as confident in my problem-solving skills or with the lab techniques and methods I’ve learned.”

Evans called the undergraduate research opportunity “incredibly important.” 

“It builds my critical thinking skills, problem-solving skills, data analysis skills, and helps me determine if I would like to pursue research as a career,” said Evans, who is in the process of applying to chemistry graduate schools. “I would like to pursue my Ph.D. in organic chemistry. Following that, I plan to attend law school, so that I can practice patent law for pharmaceuticals or another avenue of medicinal chemistry.”