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

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, sk...

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Autores principales: Perinelli, Diego Romano, Petrelli, Dezemona, Vitali, Luca Agostino, Bonacucina, Giulia, Cespi, Marco, Vllasaliu, Driton, Giorgioni, Gianfabio, Palmieri, Giovanni Filippo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631462/
https://www.ncbi.nlm.nih.gov/pubmed/31248093
http://dx.doi.org/10.3390/pharmaceutics11060287
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author Perinelli, Diego Romano
Petrelli, Dezemona
Vitali, Luca Agostino
Bonacucina, Giulia
Cespi, Marco
Vllasaliu, Driton
Giorgioni, Gianfabio
Palmieri, Giovanni Filippo
author_facet Perinelli, Diego Romano
Petrelli, Dezemona
Vitali, Luca Agostino
Bonacucina, Giulia
Cespi, Marco
Vllasaliu, Driton
Giorgioni, Gianfabio
Palmieri, Giovanni Filippo
author_sort Perinelli, Diego Romano
collection PubMed
description 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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spelling pubmed-66314622019-08-19 Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity Perinelli, Diego Romano Petrelli, Dezemona Vitali, Luca Agostino Bonacucina, Giulia Cespi, Marco Vllasaliu, Driton Giorgioni, Gianfabio Palmieri, Giovanni Filippo Pharmaceutics Article 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. MDPI 2019-06-19 /pmc/articles/PMC6631462/ /pubmed/31248093 http://dx.doi.org/10.3390/pharmaceutics11060287 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Perinelli, Diego Romano
Petrelli, Dezemona
Vitali, Luca Agostino
Bonacucina, Giulia
Cespi, Marco
Vllasaliu, Driton
Giorgioni, Gianfabio
Palmieri, Giovanni Filippo
Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity
title Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity
title_full Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity
title_fullStr Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity
title_full_unstemmed Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity
title_short Quaternary Ammonium Leucine-Based Surfactants: The Effect of a Benzyl Group on Physicochemical Properties and Antimicrobial Activity
title_sort quaternary ammonium leucine-based surfactants: the effect of a benzyl group on physicochemical properties and antimicrobial activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6631462/
https://www.ncbi.nlm.nih.gov/pubmed/31248093
http://dx.doi.org/10.3390/pharmaceutics11060287
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