The antibacterial activity of 4,4'-bipyridinium amphiphiles with conventional, bicephalic and gemini architectures

Bioorganic & Medicinal Chemistry Letters
Melissa C GrenierKevin P C Minbiole

Abstract

Dialkyl 4,4'-bipyridinium compounds are widely employed for their useful redox properties, and are commonly known as viologens due to their intense coloration upon reduction. Despite their prevalence and amphiphilic nature, the antibacterial activity of these compounds remains largely unreported. We have thus prepared a series of mono- and bis-alkylated analogs of 4,4'-bipyridine to investigate structure-activity relationships in their inhibition of a battery of Gram positive and Gram negative bacteria. The prepared cationic compounds were conventional (one cationic head, one non-polar tail), bicephalic (two heads, one tail), or gemini (two heads, two tails) in their amphiphilic structure. Additionally, an isomeric series of six bis-alkylated compounds ranging from symmetric (PQ-11,11) to highly asymmetric (PQ-20,2) were prepared. Four themes of bioactivity emerged: (1) the most bioactive compounds were gemini in structure; (2) 22 carbons in the alkyl chains, with little to modest asymmetry, led to optimal activity; (3) bicephalic compounds were generally comparable to conventional amphiphiles, though only about 12 carbons in the alkyl chains were solubilized in water by each cationic nitrogen; (4) the effects of counterion ide...Continue Reading

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Citations

Jul 10, 2015·ACS Infectious Diseases·Megan C JenningsWilliam M Wuest
Jul 6, 2013·Microbiological Research·Ewa ObłąkJacek Luczyński
Oct 22, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Allison FaigKathryn E Uhrich
Apr 11, 2017·Bioorganic & Medicinal Chemistry Letters·Ryan A AllenKevin P C Minbiole
Dec 30, 2016·ChemMedChem·Saleh E Al-KhalifaKevin P C Minbiole
Jun 12, 2016·Journal of Applied Microbiology·A PiecuchK A Wilk
Aug 26, 2014·Chembiochem : a European Journal of Chemical Biology·Megan C JenningsWilliam M Wuest
Oct 26, 2018·ChemMedChem·Renee C KontosKevin P C Minbiole
Sep 1, 2015·Chembiochem : a European Journal of Chemical Biology·Myles A MitchellKevin P C Minbiole
Feb 9, 2021·Frontiers in Chemistry·Jake R HughesPeter M Iovine
Jun 24, 2017·Colloids and Surfaces. B, Biointerfaces·Tara M GallagherKevin L Caran
Jul 3, 2021·International Journal of Molecular Sciences·Anatoly N VereshchaginValentine P Ananikov
Jul 13, 2021·ChemMedChem·Nikita A FrolovAnatoly N Vereshchagin

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