Antimicrobial activity of quaternary ammonium salts: structure-activity relationship

Nadagouda, Mallikarjuna N.; Vijayasarathy, Pooja; Sin, Aebin; Nam, Heeyeon; Khan, Sanaullah; Parambath, Javad B. M.; Mohamed, Ahmed A.; Cui, Han

doi:10.1007/s00044-022-02924-9

Cited by 68 publications

(29 citation statements)

References 70 publications

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“…Synthesis of Alkyl bisQPCs. Prior work from our groups 14,15,24 and others 25 has indicated that amphiphilic QAC and QPC compounds containing alkyl chain(s) of 10 to 12 carbon atoms generally display optimal efficacy as disinfectants. We therefore targeted the preparation of a series of compounds with alkyl chain lengths between 8 and 16 carbons to bracket this hypothesized ideal nonpolar region.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Atom Economical QPCs: Phenyl-Free Biscationic Quaternary Phosphonium Compounds as Potent Disinfectants

et al. 2023

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Quaternary ammonium compounds (QACs) are vital disinfectants for the neutralization of pathogenic bacteria in clinical, domestic, and commercial settings. After decades of dependence on QACs, the emergence of antimicrobial resistance to this class of compounds threatens the ability of existing QAC products to effectively manage rising bacterial threats. The need for new disinfectants is therefore urgent, with quaternary phosphonium compounds (QPCs) emerging as a new class of promising antimicrobials that boast significant activity against highly resistant bacteria. Reported here is a series of twenty-one novel QPCs that replace phenyl substituents on the phosphorus center with alkyl groups yet allow for rapid synthetic routes in high yields. Within this series are structures containing methyl, ethyl, or cyclohexyl phosphonium substituents on bisphosphane scaffolds bearing ethyl linkers, affording atom economical structures and ones that represent exact analogs to nitrogenous amphiphiles. The resultant bisQPC structures display high antibacterial efficacy enjoyed by comparably constructed QACs, with three structures in the singledigit micromolar activity range despite structural simplification.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Atom Economical QPCs: Phenyl-Free Biscationic Quaternary Phosphonium Compounds as Potent Disinfectants

et al. 2023

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“…Quaternary ammonium salts penetrate the cell wall of bacteria. Afterwards, reactions with lipids or proteins of the cell membrane occur, resulting in the disorganization of structures and leakage of low molecular weight components [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

Antibacterial Thin Films Deposited from Propane–Butane Mixture in Atmospheric Pressure Discharge

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et al. 2023

IJMS

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Antibacterial coatings on biomedical instruments are of great interest because they can suppress bacterial colonization on these instruments. In this study, antibacterial polymeric thin coatings were deposited on teflon substrates using atmospheric pressure plasma polymerization from a propane–butane mixture. The plasma polymerization was performed by means of surface dielectric barrier discharge burning in nitrogen at atmospheric pressure. The chemical composition of plasma polymerized propane–butane films was studied by energy-dispersive X-ray spectroscopy (EDX) and FTIR. The film surface properties were studied by SEM and by surface energy measurement. The EDX analysis showed that the films consisted of carbon, nitrogen and oxygen from ambient air. The FTIR analysis confirmed, in particular, the presence of alkyl, nitrile, acetylene, imide and amine groups. The deposited films were hydrophilic with a water contact angle in the range of 13–23∘. The thin film deposited samples were highly active against both S. aureus and E. coli strains in general. On the other hand, the films were cytocompatible, reaching more than 80% of the cell viability threshold compared to reference polystyrene tissue.

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“…71 QACs are broad-spectrum, nonspecific, membrane-destroying antibacterial agents. 35 The basic view is that QACs do not act through any privileged interactions with the bacterial biofilms and instead exert a lytic effect on the bacterial cells in the colony. 25 However, alternative mechanisms of action have been described for these compounds.…”

Section: Qacsmentioning

confidence: 99%

“…Among them, quaternary ammonium compounds (QACs) have attracted particular attention because of their excellent hard-surface cleaning and deodorizing properties, as well as a broad spectrum of antimicrobial activity. 35 They are characterized by strong biocidal action even at very low concentrations and relatively low toxicity and can be used in contact with human skin. Some commercially available and newly synthesized QACs are effective against mature biofilms both when used alone and as part of combination therapy.…”

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confidence: 99%

From Antibacterial to Antibiofilm Targeting: An Emerging Paradigm Shift in the Development of Quaternary Ammonium Compounds (QACs)

et al. 2023

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In a previous development stage, mostly individual antibacterial activity was a target in the optimization of biologically active compounds and antiseptic agents. Although this targeting is still valuable, a new trend has appeared since the discovery of superhigh resistance of bacterial cells upon their aggregation into groups. Indeed, it is now well established that the great majority of pathogenic germs are found in the environment as surface-associated microbial communities called biofilms. The protective properties of biofilms and microbial resistance, even to high concentrations of biocides, cause many chronic infections in medical settings and lead to serious economic losses in various areas. A paradigm shift from individual bacterial targeting to also affecting more complex cellular frameworks is taking place and involves multiple strategies for combating biofilms with compounds that are effective at different stages of microbiome formation. Quaternary ammonium compounds (QACs) play a key role in many of these treatments and prophylactic techniques on the basis of both the use of individual antibacterial agents and combination technologies. In this review, we summarize the literature data on the effectiveness of using commercially available and newly synthesized QACs, as well as synergistic treatment techniques based on them. As an important focus, techniques for developing and applying antimicrobial coatings that prevent the formation of biofilms on various surfaces over time are discussed. The information analyzed in this review will be useful to researchers and engineers working in many fields, including the development of a new generation of applied materials; understanding biofilm surface growth; and conducting research in medical, pharmaceutical, and materials sciences. Although regular studies of antibacterial activity are still widely conducted, a promising new trend is also to evaluate antibiofilm activity in a comprehensive study in order to meet the current requirements for the development of highly needed practical applications.

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Antimicrobial activity of quaternary ammonium salts: structure-activity relationship

Cited by 68 publications

References 70 publications

Atom Economical QPCs: Phenyl-Free Biscationic Quaternary Phosphonium Compounds as Potent Disinfectants

Atom Economical QPCs: Phenyl-Free Biscationic Quaternary Phosphonium Compounds as Potent Disinfectants

Antibacterial Thin Films Deposited from Propane–Butane Mixture in Atmospheric Pressure Discharge

From Antibacterial to Antibiofilm Targeting: An Emerging Paradigm Shift in the Development of Quaternary Ammonium Compounds (QACs)

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