Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride

Lukáč, Miloš; Mrva, Martin; Garajová, Mária; Mojžišová, Gabriela; Varinská, Lenka; Mojžiš, Ján; Sabol, Marián; Kubincová, Janka; Haragová, Hana; Ondriska, František; Devı́nsky, Ferdinand

doi:10.1016/j.ejmech.2013.05.033

Cited by 33 publications

(16 citation statements)

References 54 publications

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“…It was determined using the standard broth dilution method [55]. Their MBC values were determined and the method of testing applied within this experimental work is described in the papers [55,56].…”

Section: Determination Of Antimicrobial Activitymentioning

confidence: 99%

Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

Pisárčik

Pupák

Devı́nsky

et al. 2016

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Section: Determination Of Antimicrobial Activitymentioning

confidence: 99%

Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

Pisárčik

Pupák

Devı́nsky

et al. 2016

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…For all samples, the optical densities at 215 nm were measured at 0, 0.167, 0.33, 0.5, 0.75, 1, 1. 5,2,3,4,6,8,10,12,24,36,48,60,72,96,120,144, and 168 hours. In addition, considering that the pH value of normal human skin is between 4.0 and 6.0 and that pH at a wound site can rise to approximately 7.0 to 8.0, 14,15 the release profiles of LFFS and BZL were assessed in PBS at different pH values (pH 4.0, 6.0, and 8.0) at 37°C with the previously described methods.…”

Section: Influence Of Sustained Release In Pbsmentioning

confidence: 99%

“…Furthermore, films made of CS have been used extensively in drug delivery systems and tissue engineering scaffolds due to their biodegradability, biocompatibility, and low toxicity. 12 To date, however, an LFFS fabricated with CS and PVA for use as a BZL delivery system has not been reported.…”

Section: Introductionmentioning

confidence: 99%

Chitosan-polyvinyl alcohol nanoscale liquid film-forming system facilitates MRSA-infected wound healing by enhancing antibacterial and antibiofilm properties

Yang¹,

Yang²,

Cui³

et al. 2018

IJN

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IntroductionMethicillin-resistant Staphylococcus aureus (MRSA) is one of the most predominant and fatal pathogens at wound infection sites. MRSA is difficult to treat because of its antibiotic resistance and ability to form biofilms at the wound site.MethodsIn this study, a novel nanoscale liquid film-forming system (LFFS) loaded with benzalkonium bromide was produced based on polyvinyl alcohol and chitosan.ResultsThis LFFS showed a faster and more potent effect against MRSA252 than benzalkonium bromide aqueous solution both in vitro and in vivo. Additionally, the LFFS had a stronger ability to destroy biofilms (5 mg/mL) and inhibit their formation (1.33 μg/mL). The LFFS inflicted obvious damage to the structure and integrity of MRSA cell membranes and caused increases in the release of alkaline phosphate and lactate dehydrogenase in the relative electrical conductivity and in K+ and Mg2+ concentrations due to changes in the MRSA cell membrane permeability.ConclusionThe novel LFFS is promising as an effective system for disinfectant delivery and for application in the treatment of MRSA wound infections.

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“…In order to improve chitosan properties, attention has been recently paid to chitosan chemical modification by introducing, for example, quaternary ammonium moieties into the polymer backbone, which represents one of the most promising strategies for antimicrobial materials preparation . Quaternary ammonium salts like quinolinium, benzalkonium, and pyridinium bromide have been used as antibacterial, antiviral, and antifungal agents . The incorporation of these quaternary ammonium moieties into chitosan architecture, represents one of the most promising strategies to improve its antibacterial behavior …”

Section: Introductionmentioning

confidence: 99%

EDC‐Mediated Grafting of Quaternary Ammonium Salts onto Chitosan for Antibacterial and Thermal Properties Improvement

Oyervides–Muñoz

Avérous

Sosa‐Santillán

et al. 2019

Macro Chemistry & Physics

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The present study provides antibacterial and thermal improvements of chitosan‐based systems through chemical modification with different quaternary ammonium salts using 1‐ethyl‐3‐(3‐dimethylaminopropyl) carbodiimide (EDC) as mediator. Three different ammonium salts with a carboxylic acid end group are synthesized through a quaternization reaction between bromohexanoic acid and the respective tertiary amines (quinoline, N,N‐dimethylbenzylamine and pyridine). They are then chemically grafted along the chitosan backbone using EDC as a carboxyl activating agent for the coupling with the primary amine groups. This allows three different chitosan derivatives to be obtained: Quinolinium‐Chitosan (QA‐Cs), Benzalkonium‐Chitosan (BK‐Cs), and Pyridinium‐Chitosan (PA‐Cs), respectively. The chemical structures are characterized by 1H NMR analysis. The thermal stability is analyzed by thermogravimetric analysis. Antibacterial efficiencies of chitosan derivatives against Pseudomonas aeruginosa and Staphylococcus aureus strains are determined. All the chitosan derivatives show negligible antibacterial activity against Gram‐positive S. aureus strain. However, the antibacterial activity against Gram‐negative P. aeruginosa strain is significantly improved.

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Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride

Cited by 33 publications

References 54 publications

Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

Chitosan-polyvinyl alcohol nanoscale liquid film-forming system facilitates MRSA-infected wound healing by enhancing antibacterial and antibiofilm properties

EDC‐Mediated Grafting of Quaternary Ammonium Salts onto Chitosan for Antibacterial and Thermal Properties Improvement

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