Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč, Miloš; Devı́nsky, Ferdinand; Pisárčik, Martin; Papapetropoulou, Aspasia; Bukovský, Marián; Horváth, Branislav

doi:10.1007/s11743-016-1908-6

Cited by 26 publications

(15 citation statements)

References 70 publications

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“…Two commercially used quaternary aminium disinfectants, cetylpyridinium bromide (CPB) and benzyldodecyldimethylaminium bromide (BDDAB), were used as the reference compounds. The determination of their MBC values as well as the method of testing are described in our previous papers [ 66 , 67 ].…”

Section: Methodsmentioning

confidence: 99%

Silver Nanoparticles Stabilised by Cationic Gemini Surfactants with Variable Spacer Length

et al. 2017

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The present study is focused on the synthesis and investigation of the physicochemical and biological properties of silver nanoparticles stabilized with a series of cationic gemini surfactants having a polymethylene spacer of variable length. UV-VIS spectroscopy, dynamic light scattering, scanning electron microscopy and zeta potential measurements were applied to provide physicochemical characterization of the silver nanoparticles. The mean size values of the nanoparticles were found to be in the 50 to 115 nm range. From the nanoparticle size distributions and scanning electron microscopy images it results that a population of small nanoparticles with the size of several nanometers was confirmed if the nanoparticles were stabilized with gemini molecules with either a short methylene spacer (two or four −CH2− groups) or a long spacer (12 −CH2− groups). The average zeta potential value for silver nanoparticles stabilized with gemini molecules is roughly independent of gemini surfactant spacer length and is approx. +58 mV. An interaction model between silver nanoparticles and gemini molecules which reflects the gained experimental data, is suggested. Microbicidal activity determinations revealed that the silver nanoparticles stabilized with gemini surfactants are more efficient against Gram-negative bacteria and yeasts, which has a direct relation to the interaction mechanism of nanoparticles with the bacterial cell membrane and its structural composition.

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Section: Methodsmentioning

confidence: 99%

Silver Nanoparticles Stabilised by Cationic Gemini Surfactants with Variable Spacer Length

et al. 2017

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“…In a more recent study by Lukáč et al ., a series of 1‐alkyl‐3,4‐dimethyl‐1‐phenylphospholium bromides (Table 2) displayed similar correlations between chain length and bioactivity in QPCs [27] . QPCs 5 showed stronger bioactivity against S. aureus as compared to the Gram‐negative E. coli , in some cases over a 10‐fold difference in minimum bactericidal concentration (MBC).…”

Section: Quaternary Phosphonium Compounds As Small Molecule Antisepticsmentioning

confidence: 90%

Advancements in the Development of Non‐Nitrogen‐Based Amphiphilic Antiseptics to Overcome Pathogenic Bacterial Resistance

et al. 2020

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The prevalence of quaternary ammonium compounds (QACs) as common disinfecting agents for the past century has led bacteria to develop resistance to such compounds. Given the alarming increase in resistant strains, new strategies are required to combat this rise in resistance. Recent efforts to probe and combat bacterial resistance have focused on studies of multiQACs. Relatively unexplored, however, have been changes to the primary atom bearing positive charge in these antiseptics. Here we review the current state of the field of both phosphonium and sulfonium amphiphilic antiseptics, both of which hold promise as novel means to address bacterial resistance.

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“…The measurements of equilibrium surface tension and electrical conductivity were carried out according to the previously described procedure (Lukáč et al, 2017).…”

Section: Methodsmentioning

confidence: 99%

“…Their preparation is easier than that of trialkylphosphonium salts. Trialkylphosphines are more sensitive to oxidation than triarylphosphines (Lukáč et al, 2017). As with QAC, they also show antimicrobial activities (Bittner Fialová et al, 2019; Lukáč et al, 2017; Tatarinov et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

“…Trialkylphosphines are more sensitive to oxidation than triarylphosphines (Lukáč et al, 2017). As with QAC, they also show antimicrobial activities (Bittner Fialová et al, 2019; Lukáč et al, 2017; Tatarinov et al, 2018). However, they are intensively studied for their unique ability to target compounds to mitochondria (Zielonka et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Surface Activity, and Biological Activities of Phosphonium and Metronidazole Salts

Lukáč

Pisárčik

Garajová

et al. 2020

J Surfact & Detergents

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A series of phosphonium amphiphilic compounds was synthesized. Cationic parts of molecules contain triphenylphosphonium moieties. Lipophilic parts of compounds are represented by straight alkyl chain or the alkyl chains which are ornamented by benzyl or metronidazole. The physicochemical properties of phosphonium amphiphilic compounds were investigated by the measurements of surface tension and conductivity. The critical micelle concentration (cmc), the surface tension value at the cmc (γ cmc), the surface area at the surface saturation per head group (A cmc) were determined. The lowest cmc value was determined for phosphonium salts with straight dodecyl alkyl chain. Its value was 1.5 × 10 −3 mol dm −3. Surface tension at the cmc decreases with the addition of bulky moieties (benzyl, radical from metronidazol) at the end of alkyl chains. Biological activities of compounds were studied on human erythrocytes and strains of Acanthamoeba lugdunensis and Acanthamoeba quina. Dodecyltriphenylphosphonium bromide showed the highest activity against Acanthamoeba. To the best of our knowledge, it is the first compound of the group of phosphonium amphiphiles, which exhibited high activity against Acanthamoeba. The determined structure-activity relationship indicated nonspecific trophocidal and hemolytic activity that depends on physicochemical properties of the studied compounds.

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Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Cited by 26 publications

References 70 publications

Silver Nanoparticles Stabilised by Cationic Gemini Surfactants with Variable Spacer Length

Silver Nanoparticles Stabilised by Cationic Gemini Surfactants with Variable Spacer Length

Advancements in the Development of Non‐Nitrogen‐Based Amphiphilic Antiseptics to Overcome Pathogenic Bacterial Resistance

Synthesis, Surface Activity, and Biological Activities of Phosphonium and Metronidazole Salts

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