Festival of Science, Scholarship, and Creativity 2024
At St. Lawrence University Festival of Science, Scholarship and Creativity on April 26, 2024, Chemistry students doing research in the Chemistry Department presented their results.
Presenter: Bobby Tremont, Faculty Sponsor: Samuel Tartakoff, Department Chemistry
“First Across the NASH Finish Line: A Multifaceted Analysis of Madrigal Pharmaceutical and their THR-β agonist resmetirom”
Abstract: On March 14th, Madrigal Pharmaceuticals became the first and only FDA approved nonalcoholic steatohepatitis (NASH) drug. NASH is a liver disease that effects 1.5 million Americans and no previous treatments could improve fibrosis to resolve NASH. My research analyzes Madrigal’s drug resmetirom from discovery to early commercialization rollout. This is done through examining the biochemistry, chemistry, clinical outcomes, safety profile, market response, and financials of the drug and Madrigal. The goal of this research is to better understand how each of these factors helped and/or hindered resmetirom’s success. This allows the potential to better understand and predict future trends within the NASH drug space and in the broader pharmaceutical industry.
Presenter: Brooke Westcom, Faculty Sponsor: Samantha Glazier, Department Chemistry
“Analysis of M-MIP-modified Amino-Carbon Dots Synthesis for Detection of TNT”
Abstract: Amino-carbon dots are a type of quantum dot made of carbon nanomaterial and have been an effective way to detect harmful heavy metals and explosives such as 2-methyl-1,3,5-trinitrobenzene (TNT). Through fluorescence quenching, these dots help detect TNT in contaminated sources. While the carbon dots are promising, selectivity is an area of ongoing research because they are non-specific and false positives are possible due to decay products of target molecules. Mesoporous molecularly imprinted polymers (M-MIPs) are a new approach to improving selectivity. M-MIPs are polymers that have been synthesized and cast around a template molecule, leaving cavities and space where only targeted molecules can bind. If a sample contained TNT, it would bind to the M-MIP modified amino-carbon dot and change the fluorescence. The exact procedure and mechanism of the amino-carbon dot reactions have not been determined; there is variation in reports about the effects of reaction time, temperature and dialysis on the chemical structure and associated sensitivity to TNT. We will use Raman and infrared spectroscopy to understand how different synthetic protocols impact chemical structures of the M-MIPs. Once the synthesis is optimized, fluorescent titrations will be used to investigate sensitivity and selectivity of M-MIPs to trinitrotoluenes.
Presenter: Corryn Canell, Faculty Sponsor: Amanda Oldacre, Department: Chemistry
“Investigation of Azo Dye Degradation Using Porphyrins as Electrocatalysts”
Abstract: Investigating and improving the negative effects of azo dyes is extremely important in refining the overall health of humans and the well-being of the environment. Decreasing the amount of dye found in an isolated system and degrading it will allow pathways for similar experiments in larger bodies of water. In this investigation, we initially synthesized a metal-organic framework (MOF) through the addition of zirconyl chloride octahydrate and tetra(4-carboxyphenyl)porphyrin, making MOF-525. Using Lewis acid/base chemistry, we were able to facilely synthesize a MOF with a catalytic center integrated within its framework. Activation of the MOF was then completed to ensure its large pore sizes were not occupied with another chemical. The MOF acts as a sponge to adsorb dye thereby decreasing its concentration in water. MOF-525 was then used for sequestration of the azo dye, methyl orange, from distilled water. The concentration of a methyl orange stock solution was varied as well as the amount of MOF used in order to observe any sequestration changes. Greater amounts of MOF in solution will cause a more significant decrease in the absorbance of a methyl orange stock solution.
Presenter: Lucy Albrecht, Faculty Sponsor: Stephanie Tartakoff, Department: Chemistry
“The Key To Humanity: Dopamine”
“Abstract: Dopamine is a powerful and versatile molecule with impacts on human life needs and natural urges like fueling our bodies, learning, motivation and pleasure. Unraveling effects of dopamine is vital in being able to treat various health issues and understand human reward systems. Dopamine’s structure as a neurotransmitter and hormone is key to finding its various areas of health impact. Its social presence can be used to find reason behind urges, emotions and addictions. Through dopamine’s concentration or lack thereof in human bodies, it can impair motor functions in patients with Parkinson’s disease, and cognitive function with its role in conditions of Alzheimer’s, ADHD, schizophrenia and depression. Within society it feeds addiction, impairing natural reward systems. Recent research shows that music can activate the dopamine reward system and can be used to have medicinal benefits influencing emotion, arousal and memory.
Presenter: Leana Dickhens, Faculty Sponsor: Samuel Tartakoff, Department: Chemistry
“Further Improvements of the Wagner-Jauregg Reaction and Exploration of Morphine Analogues”
Abstract: Opioid molecules, naturally derived from the poppy plant, are responsible for physiological effects that have grabbed the attention of many scientists. These molecules are prescribed for pain relief and are associated with a “high” feeling as well as total relaxation. Some of these drugs include morphine, codeine, and oxycodone. While they minimize pain, they also threaten addiction. The Diels-Alder reaction, discovered in 1928 by Otto Diels and Kurt Alder, was recognized for its ability to combine simple molecules into complex molecules related to natural products, like opioids. Theodor Wagner-Jauregg discovered the Wagner-Jauregg reaction, which involves a double Diels-Alder reaction, two years later, although limited work has been published on this reaction. The purpose of my research is to synthesize a library of polycyclic molecules resembling the morphine core structure using the Wagner-Jauregg reaction. Although further research and reaction optimization is necessary first, it is predicted that the Wagner-Jauregg reaction can be used to make morphine analogues, with different biological properties and the possibility of less harmful side-effects. My research focused on tri-substituted aryl dienes, and their use in the Wagner-Jauregg reaction.
Presenter: Melinda Barath, Faculty Sponsor: Amanda Oldacre, Department: Chemistry
“Methyl Orange Stability Testing Using Electrochemistry Techniques and Bulk Electrolysis”
Abstract: The textile industry has become an instrumental part of the day-to-day activities of many people, especially when it comes to clothing. Around 60% of the synthetic dyes used in the industry are part of the azo dye organic family, characterized by the azo bond (nitrogen – nitrogen double bond). One such example is methyl orange, with its orange color apparent when dissolved in water. Given the heavy usage of these synthetic dyes, they are now ubiquitous in the environment, such as in bodies of water, which poses a significant issue due to the protoxicant nature of the dye. Upon degradation, the azo bond is reduced to create two planar aryl amines, which can slide in between the base pairs of DNA, acting as an intercalator. It is imperative to discover a degradation pathway that eliminates toxic by-products that are detrimental to aquatic life. Using a porphyrin metal-organic framework (MOF), the methyl orange can be sequestered from various bodies of water, as well as oxidized. To determine whether the MOF is responsible for the degradation of the dye, there were control experiments done with cyclic voltammetry in neutral pH water, where there were irreversible oxidation events occurring at around 0.80 V vs. the Ag/AgCl reference electrode with an ITO working electrode. Additionally, bulk electrolysis control experiments were also performed, where the absorbance of the methyl orange solution decreased over time.
Presenter: Madison Ruggiera, Faculty Sponsor: Samuel Tartakoff, Department: Chemistry
“Synthesis of Novel Proflavine Derivatives as Possible DNA Binding Agents”
Abstract: Organic synthesis gives medicinal chemists the ability to create complex molecules from cheap and readily available chemical compounds. Many of these complex organic compounds are bioactive molecules that can function as DNA intercalators— molecules that bind to DNA in a variety of modes, causing a change in the DNA conformation. This change often results in a halt in cell function or cell death, making intercalating molecules valuable chemotherapeutic agents. This project centers around creating derivatives from a known intercalating molecule, proflavine, in order to create DNA intercalators that are more soluble in water and more electrophilic, allowing for these analogue-molecules to more effectively bind to DNA. While utilizing literature and known reactions, a small library of proflavine derivatives is being created based on the condensation of functional groups onto proflavine’s unsubstituted amines, as well as rebuilding the core acridine structure of proflavine to include reactive groups on the aromatic rings. The goal of this project is the creation of both known and novel proflavine derivatives for use in DNA-binding and kinetics studies.
Presenter: Nadine Manase, Faculty Sponsor: J. Patrick Lutz, Department: Chemistry
“Poly(Glyoxylates) and Poly(Glyoxylamides) as Selfimmolative Polymers for Plastic Synthesis”
Abstract: Plastics are all around us in materials that are used daily. Due to their usefulness, plastics are widely produced, but estimates suggest that only 9% of plastic has been successfully recycled. Much of the rest of the plastic end up in landfills and oceans where it can release toxic substances. Even for plastics that can be recycled, it is usually cheaper to make new plastic than to recycle used plastic. A more sustainable plastics economy would use closed-loop recycling, but few materials are amenable to this type of process.
This research aimed at measuring thermodynamic parameters of self-immolative poly(glyoxylamides), which represent a class of materials that can be readily depolymerized and potentially recycled. Understanding these parameters will aid in designing new recyclable materials.
The research started with synthesizing the monomer 2-oxo-2-(pyrrolidin-1-yl)acetaldehyde. This aldehyde was prepared through a sequence of three reactions. While we were able to successfully prepare the target monomer, we found that the compound was extremely hygroscopic: it rapidly reacts with water, to form a hydrate that is unable to undergo the target polymerization reaction. We examined a number of different strategies to remove water and found that using a Dean–Stark reaction could afford the aldehyde monomer in approximately 90% purity. However, even the small amount of water remaining was enough to impede successful polymerization. Future studies could explore more methods for purifying the target monomer or alternate strategies to access the target polymer via post-polymerization modification to enable measuring the thermodynamic properties.
Despite the challenges we encountered, I was able to learn a lot of new skills such as running organic reactions under inert atmosphere, performing 1H and 13C NMR spectroscopy, and analyzing spectral data. I was also glad to be able to put to practice my Organic Chemistry knowledge from my classes.
Presenter: Elise Heppell, Faculty Sponsor: Stephanie Tartakoff, Department: Chemistry
“An Introduction to Menthol: A Fresh Take on a Cool Compound”
Abstract: Menthol, the molecule responsible for the cool sensation from eating a peppermint, is best known for its use as an additive to gum, toothpaste and candy. However, menthol has an impressive range of biological uses as well: it has anticancer, antibacterial and anti-itch properties, combats memory loss from Alzheimer’s disease, and is effective as an insect repellent. Menthol may become an important medicinal compound as researchers learn more about how it functions in these roles. It also has played a major role in public health as an additive to cigarettes. Menthol makes smoking less unpleasant by soothing the throat, and more addictive by boosting dopamine release in the brain. Since mentholated cigarettes are highly popular among youth smokers and Black smokers, the recent ban on mentholated cigarettes in the United States is expected to decrease the total number of smokers, as youth smokers often become addicted with menthol cigarettes, and help combat racial public health disparity.
Presenter: Emma Rothe, Faculty Sponsor: J. Patrick Lutz, Department: Chemistry
“Synthesis of acridine derivatives as potential chemotherapeutic agents”
Abstract: This research aimed to synthesize degradable polymers based on the azulene framework. Azulene is an aromatic hydrocarbon with a unique structure consisting of fused five- and seven-membered rings that leads to surprising chemical properties such as a relatively large dipole moment, pH-responsive behavior, and vibrant colors. While a number of azulene-containing polymers are known, previous work has not focused on degradable materials. Our approach was to functionalize azulene derivatives with the aldehyde functional group, which we hypothesized could be polymerized to form acid-degradable polyacetals. We were successful in synthesizing both monoaldehyde- and dialdehyde-substituted azulene derivatives, but to date have been unable to demonstrate polymerization of these materials. Further research should be done to assess whether the lack of polymerization arises from low reactivity of the aldehyde monomers, catalyst inhibition by the monomers or some impurity, or another reason. Continued investigation of these reactions could be beneficial in helping to increase sustainability by generating new plastics that are easily degradable, helping to reduce the environmental impact of these materials.
Presenter: Leah Biwot, Faculty Sponsors: Samuel Tartakoff and Samantha Glazier, Department: Chemistry
“Synthesis of acridine derivatives as potential chemotherapeutic agents”
Abstract: Acridine dyes are commonly used for DNA-drug interaction studies because their polycyclic, planar, and aromatic structures can intercalate between adjacent DNA bases, stopping transcription and serving as potential chemotherapeutic agents. In my research, I have prepared a number of acridine derivatives to better understand DNA-ligand interactions and structure-activity relationships. These derivatives were prepared using two approaches: (1) by directly modifying proflavine with various reactions (e.g., amine acylation and aromatic substitution) and (2) by using the Ullman-Goldberg cross-coupling reaction to build up the acridine core, which allows for the introduction of more substituents via later nucleophilic substitution of the resultant 9-chloroacridines. I have also investigated the methylation of the aromatic acridine nitrogen to render the resulting products water-soluble and facilitate binding studies with DNA via a range of techniques, including melting point, viscosity, circular dichroism (CD), and kinetics. These studies will provide insight into how various functional groups affect the binding modes and intercalation properties of acridine derivatives.
Presenter: Mia Marino, Faculty Sponsor: Stephanie Tartakoff, Department: Chemistry
“Melatonin: Still Not Melanin”
Abstract: Studies have shown that melatonin can be used for the treatment of sleep disorders and other neurological disorders that affect the circadian rhythm. Research on melatonin has shown that it is one way to help treat sleep disorders, as synthetic supplementation of the molecule can help humans become drowsy faster. However, its use in other neurological disorders like ADHD has not been as prevalent, even though it is effective in the studies found. Future research is needed to explore the impacts of melatonin on individuals with these neurological disorders. However, those who took the melatonin treatment were able to fall asleep relatively faster than those who didn’t.
Presenter: Lydia Oikonomou, Faculty Sponsor: Nadia Marano, Department Chemistry
“Biofilm formation and amyloid protein production of three strains of bacteria isolated from water bottle filling stations.”
Abstract: Drinking water fountains and water bottle filling stations can be a breeding ground for bacteria that originate either from the environment or from the people that use these stations. The ability of bacteria to survive on surfaces depends on their capability to become attached to the surface of the bottle filling stations and form biofilms. Biofilms are communities of bacteria that are surrounded by an extracellular matrix which renders them resistant to disinfecting agents. This extracellular matrix can be composed of a mixture of macromolecules such as polysaccharides, proteoglycans, and amyloid proteins. The purpose of this study was to understand the kinetics of the formation of biofilms and attachment of amyloid proteins. Three bacterial strains (Acidovorax, Deinococcus, Rhizobium rosettiformans) previously isolated from water bottle filling stations were selected for analysis. The bacteria were grown in R2A solid media and isolated colonies were used to inoculate R2A liquid media. The absorbance at 600 nm was monitored every 24 hours for 6 days in order to construct growth curves for each of the four strains. For determining biofilm formation, the crystal violet biofilm assay was utilized. Amyloid production was detected using the thioflavin-T assay at different time points during growth. It was determined that Rhizobium rosettiformans had the highest ability to form biofilm and amyloid protein production. However, Deinococcus had the highest growth.
Presenter Blake Heston, Faculty Sponsor: J. Patrick Lutz, Department: Chemistry
“Synthesis and Analysis of Novel Self-Immolative Copolymers”
Abstract: Our world today relies heavily on plastics (polymers) that are hazardous for the environment in both the unsustainable production of these materials from petroleum feedstocks and the negative impacts of plastic waste. While most commercial polymers cannot be efficiently degraded back to their monomers, developing polymers that can be depolymerized could facilitate recycling, increasing the sustainability of polymers. Self-immolative polymers have the ability to address these challenges because they readily fragment back into the monomer if an appropriate catalyst or initiator is introduced above a threshold known as the ceiling temperature. In this project we looked at the reactivity of phenylglyoxal as a comonomer in polymerization with o-phthalaldehyde (OPA). The OPA monomer is known to polymerize at temperatures below -38 ºC under cationic and anionic polymerizations conditions. In our studies, we observed incorporation of both monomers to form a copolymer, though homopolymerizaiton of phenylglyoxal was unsuccessful. Future research will focus on quantifying the monomer ratio in the copolymer and analyzing the thermal and thermodynamic of these novel copolymers.