From antimicrobial activity to mechanism of resistance: the multifaceted role of simple quaternary ammonium compounds in bacterial eradication

Quaternary ammonium compounds (QACs) are a prominent class of antibacterial agents. Drawing inspiration from commercial disinfectants and antimicrobial natural products, we have derivatized structurally diverse tertiary amines to generate several different classes of QACs. We have synthesized over 2...

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Bibliographic Details
Published in:Tetrahedron 2016-06, Vol.72 (25), p.3559-3566
Main Authors: Minbiole, Kevin P.C., Jennings, Megan C., Ator, Laura E., Black, Jacob W., Grenier, Melissa C., LaDow, Jade E., Caran, Kevin L., Seifert, Kyle, Wuest, William M.
Format: Article
Language:English
Subjects:
Ammonium compounds
Amphiphile
Antibacterial
Antibiofilm
Antiinfectives and antibacterials
Bacteria
Inspiration
Light-emitting diodes
MRSA
MultiQAC
Quaternary ammonium compound
Staphylococcus aureus
Tetrahedrons
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Summary:Quaternary ammonium compounds (QACs) are a prominent class of antibacterial agents. Drawing inspiration from commercial disinfectants and antimicrobial natural products, we have derivatized structurally diverse tertiary amines to generate several different classes of QACs. We have synthesized over 200 QACs, many of which exhibit potent antibacterial and antibiofilm activity. Analysis of the structure–activity relationship of our compounds have led to the facile production of inexpensive QACs that display ∼1 μM MIC against a suite of bacteria, and furthermore do not appear to trigger bacterial resistance systems in methicillin-resistant Staphylococcus aureus (MRSA). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.01.014