Document Type
Thesis
Date of Award
2022
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
Pere Miro, Bess Vlaisavljevich
Abstract
Biofilms are the default state of microbial life and their formation on surfaces influences many processes. The coordinated behavior of microorganisms including their growth into biofilms occurs through a process termed quorum sensing during which they excrete specific signaling molecules called autoinducers. Recently it has been observed that Ag+ and Cu2+ ions interact with N-hexanoyl-L-homoserine autoinducers thereby inhibiting quorum sensing. Such inhibitors are called quorum quenchers. In this study, we have used density functional theory (DFT) calculations to study the ion pairing between select cations and short chained N-acyl-homoserine lactone (AHL) type autoinducers that are used by gram negative bacteria. We demonstrate that pairing of the cations to these autoinducers occurs at the carbonyl groups and examine how different R groups effect this interaction. The binding motifs with higher denticity resulted in stronger DFT pairing energies. DFT calculations showed that the carbon chain length has little impact on the strength of the ion pairing energy for a contact ion pair when it was varied from 2 to 4 carbons for the studied autoinducers. Ca2+ was the only ion studied that did not have a favorable contact ion pair at the DFT level of theory.
Subject Categories
Chemistry
Keywords
Biofilms, Quorum Quenching
Number of Pages
39
Publisher
University of South Dakota
Recommended Citation
Suduweli Kondage, Ashen Anuradha, "Computational Study of Quorum Quenching of N-Acyl Homoserine Lactones by Ion Pairing to Cations" (2022). Dissertations and Theses. 48.
https://red.library.usd.edu/diss-thesis/48