Quaternary ammonium surfactants derived from leucine and methionine: Novel challenging surface active molecules with antimicrobial activity

Perinelli, Diego Romano; Petrelli, Dezemona; Vitali, Luca Agostino; Vllasaliu, Driton; Cespi, Marco; Giorgioni, Gianfabio; Elmowafy, Enas; Bonacucina, Giulia; Palmieri, G

doi:10.1016/j.molliq.2019.03.083

Cited by 31 publications

(19 citation statements)

References 53 publications

(58 reference statements)

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“…The cytotoxicity of the N -benzyl quaternary ammonium surfactants derived from leucine in comparison to the commercial BAC was studied by performing two cytotoxicity assays (MTS and LDH as indicators of metabolic activity and membrane integrity, respectively) and by a haemolytic assay. The assays were conducted as reported in our previous publications [5,14]. EC 50 values from the MTS assay (concentration of surfactant that causes 50% cell death) and the LDH assay (concentration of surfactants that causes 50% LDH release from cells), as well as HC 50 values from the haemolytic assay (concentration of surfactants that causes 50% haemoglobin release from erythrocytes) were calculated using a nonlinear regression model (Prism version 5.0, GraphPad Inc., San Diego, CA, USA) as follows:Y=BOTTOM+Top−Bottom1+10(LogEC50−normalx) Hill Slope where Top and Bottom are plateaux in the units of the Y axis.…”

Section: Methodsmentioning

confidence: 99%

“…In a previous paper, we synthesised and characterised the surface activity, cytotoxicity, and antimicrobial properties of two series of linear quaternary ammonium compounds, based on the amino acid leucine and methionine and with different hydrophobic chain lengths (C10, C12 and C14). These amphiphiles, especially derivatives with a C12 and C14 hydrocarbon chain, showed a satisfactory cytotoxicity and an antibacterial profile that was comparable to benzalkonium chloride (BAC), with higher activity observed against Gram-positive bacteria [14]. In the present work, we report the synthesis of the same series of leucine-based surfactants by introducing an N -benzyl group, which is a common substituent of commercial quaternary ammonium compounds (e.g., benzalkonium chloride).…”

Section: Introductionmentioning

confidence: 99%

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Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

et al. 2019

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Quaternary ammonium amphiphiles are a class of compounds with a wide range of commercial and industrial uses. In the pharmaceutical field, the most common quaternary ammonium surfactant is benzalkonium chloride (BAC), which is employed as a preservative in several topical formulations for ocular, skin, or nasal application. Despite the broad antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as fungi and small enveloped viruses, safety concerns regarding its irritant and cytotoxic effect on epithelial cells still remain. In this work, quaternary ammonium derivatives of leucine esters (C10, C12 and C14) were synthesised as BAC analogues. These cationic surfactants were characterised in terms of critical micelle concentration (CMC, by tensiometry), cytotoxicity (MTS and LDH assays on the Caco-2 and Calu-3 cell lines) and antimicrobial activity on the bacterial species Staphylococcus aureus and Enterococcus faecalis among the Gram-positives, Escherichia coli and Pseudomonas aeruginosa among the Gram-negatives and the yeast Candida albicans. They showed satisfactory surface-active properties, and a cytotoxic effect that was dependent on the length of the hydrophobic chain. Lower minimum inhibiting concentration (MIC) values were calculated for C14-derivatives, which were comparable to those calculated for BAC toward Gram-positive bacteria and slightly higher for Gram-negative bacteria and C. albicans. Thus, the synthesised leucine-based quaternary ammonium cationic surfactants can potentially find application as promising surface-active compounds with antimicrobial activity.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

et al. 2019

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“…Actually, the most numerous groups of compounds used as chemical inhibitors of biocorrosion are nitrogen compounds, including aliphatic amines such as N-(3-aminopropyl) -N-dodecylpropane 1,3-diamine and quaternary alkylammonium salts such as chloride didecyldimethylammonium [79]. Based on the literature [80,81] it is well-known that biocidal preparations containing quaternary alkylammonium salts or the newest quaternary ammonium surfactants [81], as active substances, are effective in limiting fungal population and cause no damage or physical changes on disinfected surfaces. Adsorption of these compounds on inanimate surfaces cause removal of water molecules and forming a monomolecular protective salt layer of alkylammonium, which protects the material against corrosion in the future.…”

Section: Discussionmentioning

confidence: 99%

“…Adsorption of these compounds on inanimate surfaces cause removal of water molecules and forming a monomolecular protective salt layer of alkylammonium, which protects the material against corrosion in the future. Quaternary alkylammonium salts are not reactive, which is why they adsorb on surfaces and do not induce any chemical reactions [80,81]. Considering the above, it was strongly recommended to use preparation from this group in the studied cave.…”

Section: Discussionmentioning

confidence: 99%

Diversity of Species and Susceptibility Phenotypes toward Commercially Available Fungicides of Cultivable Fungi Colonizing Bones of Ursus spelaeus on Display in Niedźwiedzia Cave (Kletno, Poland)

Dyląg

Sawicki²,

Ogórek

2019

Diversity

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Underground ecosystems are one of the most inhospitable places for microorganism development and function. Therefore, any organic matter located in these areas can stimulate fungal growth. The main purpose of this study was to find the best solution to effectively preserve (without relapses) paleolithic bones of cave bear (Ursus spelaeus) exhibited in cave without any negative influence on the cave environment. To achieve this aim, unambiguous identification of fungal species and its susceptibility tests toward fungicidal preparations were performed. Fungi were identified based on phenotypic tests and the internal transcribed spacer (ITS) region analysis. The antifungal activity of three preparations (Pufmax, Boramon and Devor Mousse) was evaluated by microdilution assay (protocol M38-A2) and spot tests assay. Phenotypic and molecular research showed that bones were colonized by 11 fungal species: Absidia glauca, Aspergillus fumigatus, Chrysosporium merdarium, Fusarium cerealis, Mortierella alpina, Mucor aligarensis, M. plumbeus, Penicillium chrysogenum, P. expansum, Sarocladium strictum and Scopulariopsis candida. All of the tested preparations were the most active against C. merdarium. In turn, M. plumbeus, M. aligarensis, M. alpina and A. glauca were the least susceptible. The highest antifungal activity was shown for Pufmax (minimum inhibitory concentration (MIC) and minimal fungicidal concentration (MFC) values were in the range of 0.16–0.63% and 1.25–2.50%, respectively). The lowest fungicidal effect was observed for Boramon (MICs and MFCs in the range of 2.5–10% and 5–20%, respectively). Devor Mousse and Pufmax preparations showed fungicidal activity at the concentrations in the range of 1.25–5%. Susceptibility profiles were also confirmed based on spot tests assay. Our study allows for unambiguously identifying isolated fungi and assessing their susceptibility to commercially available fungicides, to prevent fungal outbreak.

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“… 13 In another study, the antimicrobial activity of leucine- and methionine-based esters was shown against bacteria and yeast. 14 Encouraged by these results, we synthesized arginine esters with C 18 and C 24 carbon chains, namely, arginine-oleate and arginine-decyltetradecanoate esters (Arg-OL and Arg-DT). Oleyl alcohol was chosen because of its monounsaturated hydrophobic tail, providing a comparatively bulky lipophilic group, and 2-decyl-1-tetradecanol was chosen because of its branched lipophilic structure.…”

Section: Introductionmentioning

confidence: 99%

Lipophilic Arginine Esters: The Gateway to Preservatives without Side Effects

et al. 2020

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This study hypothesized that long carbon chain cationic arginine (Arg) esters can be considered as toxicologically harmless preservatives. Arg-esters with C 18 and C 24 carbon chains, namely, arginine-oleate (Arg-OL) and arginine-decyltetradecanoate (Arg-DT), were synthesized. Structures were confirmed by FT-IR, 1 H NMR, and mass spectroscopy. Both Arg-esters were tested regarding hydrophobicity in terms of log P octanol/water , critical micelle concentration (CMC), biodegradability, cytotoxicity, hemolysis, and antimicrobial activity against Escherichia coli ( E . coli ), Staphylococcus aureus ( S . aureus ), Bacillus subtilis ( B . subtilis ), and Enterococcus faecalis ( E . faecalis ). Log P octanol/water of arginine was raised from −1.9 to 0.3 and 0.6 due to the attachment of C 18 and C 24 carbon chains, respectively. The critical micelle concentration of Arg-OL and Arg-DT was 0.52 and 0.013 mM, respectively. Both Arg-esters were biodegradable by porcine pancreatic lipase. In comparison to the well-established antimicrobials, benzalkonium chloride (BAC) and cetrimide, Arg-esters showed significantly less cytotoxic and hemolytic activity. Both esters exhibited pronounced antimicrobial properties against Gram-positive and Gram-negative bacteria comparable to that of BAC and cetrimide. The minimum inhibitory concentration (MIC) of Arg-esters was <50 μg mL –1 against all tested microbes. Overall, results showed a high potential of Arg-esters with long carbon chains as toxicologically harmless novel preservatives.

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Quaternary ammonium surfactants derived from leucine and methionine: Novel challenging surface active molecules with antimicrobial activity

Cited by 31 publications

References 53 publications

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity

Diversity of Species and Susceptibility Phenotypes toward Commercially Available Fungicides of Cultivable Fungi Colonizing Bones of Ursus spelaeus on Display in Niedźwiedzia Cave (Kletno, Poland)

Lipophilic Arginine Esters: The Gateway to Preservatives without Side Effects

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