Date Approved

9-8-2026

Embargo Period

9-8-2026

Document Type

Thesis

Degree Name

M.S. Pharmaceutical Sciences

Department

Chemistry and Biochemistry

College

College of Science & Mathematics

Advisor

Timothy D. Vaden, Ph.D.

Committee Member 1

Gregory A. Caputo, Ph.D.

Committee Member 2

Benjamin Carone, Ph.D.

Disciplines

Chemistry | Physical Sciences and Mathematics

Abstract

Fatty acid ionic liquids (FAILs) are a class of ionic liquids (ILs) with relatively low toxicity and potential applications in biological systems. This study examined the interactions of tetramethylguanidinium decanoate, tetramethylguanidinium octanoate, choline decanoate, and choline octanoate with lipid membranes, proteins, and nucleic acids. Membrane leakage experiments using model lipid vesicles showed that decanoate-based FAILs produced greater membrane permeabilization than octanoate-based analogues, consistent with their higher membrane permeability. These effects were stronger for the ILs than for decanoate alone and occurred below the critical micelle concentration (CMC), suggesting that micelle formation may not be essential for membrane disruption. The ability of FAILs to self-assemble also indicates their potential for stabilizing G-quadruplex RNA through encapsulation. Protein interactions were investigated using azurin as a model protein. Thermal unfolding studies showed that tetramethylguanidinium decanoate and choline decanoate destabilized azurin at concentrations above their CMC values, while decanoic acid alone had little effect. Overall, this study demonstrates that both ionic interactions and self-assembly contribute to the biological activity of FAILs and support their potential use in biomolecular and biomedical applications.

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