Biologically active aromatic acids in phosphatidylcholine liposomes: benzoic and salicylic acids
Date
2022
Authors
Sanders, Sarah Ivy, author
Crans, Debbie, advisor
Van Orden, Alan, committee member
Van Buiten, Charlene, committee member
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Abstract
The interactions of benzoic acid and salicylic acid with phosphatidylcholine liposomes were characterized to understand interfacial interactions of the two weak aromatic acids with the membrane. The liposomal system was comprised of soy l-ɑ-phosphatidylcholine (SPC) bilayers, which allowed the determination of interfacial interactions and position within the membrane using 1D 1H NMR. Benzoic acid was considered due to its effects as a food stabilizer, where salicylic acid was considered as a derivative due to its effects as an anti-acne agent. Both were found to penetrate the membrane interface deeper when in their protonated forms. The presence of the weak acids on the membrane surface allowed stabilization through hydrogen bonding with liposomal headgroups, which allowed deprotonation to occur. Broadening of aromatic peaks demonstrated a pH dependence for both benzoic acid and salicylic acid, showing a deeper penetration around the pKa values of the weak acids. This study offers justification for the antimicrobial activity of benzoic and salicylic acids in lower pH environments. Thus, this study provides the next piece in understanding the uptake of benzoic acid and salicylic acid in bacteria for microbial inhibition.
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Subject
benzoic acid
interfacial interactions
salicylic acid
food stabilizer
anti-acne agent
phosphatidylcholine liposome