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

ABSTRACT: 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.

SUBMITTER: Perinelli DR

PROVIDER: S-EPMC6631462 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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

Perinelli Diego Romano DR Petrelli Dezemona D Vitali Luca Agostino LA Bonacucina Giulia G Cespi Marco M Vllasaliu Driton D Giorgioni Gianfabio G Palmieri Giovanni Filippo GF

Pharmaceutics 20190619 6

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 irritan ...[more]

PMID: 31248093

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Project description:Research conducted both prior to and after the emergence of the COVID-19 pandemic reveals a notable rise in human exposure to cleaning products, hand sanitizers, and personal care items. Moreover, there has been a corresponding increase in the environmental release of these chemicals. Cleaning and disinfecting products often contain quaternary ammonium compounds (QACs) with alkyl chains as long as 8-12 carbon atoms. The attachment of quaternary ammonium surfactants to the membrane resulted in the deformation of the bilayer and membrane disruption. Before interactions with cell membranes, these surfactant molecules may form different aggregates depending on their architecture. Interaction of surfactant monomers or clusters with the cell membrane changes the physiochemical properties of the biomembranes. To investigate this interaction and its influence on membrane properties, we conducted molecular dynamics simulations of cationic quaternary ammonium surfactants interacting with dipalmitoylphosphatidylcholine (DPPC) membranes. Our simulations revealed significant interactions between the surfactants and the phospholipids, leading to substantial alterations in the structure of the bilayer. The results are compared with the simulated anionic (SDS) and nonionic surfactants/bilayer systems. Various aspects were considered, including the aggregation process, migration behavior, and eventual equilibrium of these molecules at the interface between the membrane and water. This analysis used various techniques such as density profiles, distribution functions, cluster analysis, order parameters, hydrogen bonding (H-bonding), and mean-square displacements. The results indicate that while surfactants with shorter alkyl tails (N-(2-hydroxyethyl)-N,N-dimethyloctan-1-aminium chloride (HEDMOAC)) make strong hydrogen bonds with the phosphate group and ester oxygen of the phosphatidylcholine bilayer and enter toward the bilayer in the monomer form, surfactants of longer alkyl tails aggregated on the membrane head-water interface and interact minimally with the head groups of the DPPC bilayer. For DDEDMEAC, a quaternary ammonium surfactant with a hydrophobic alkyl chain consisting of two decanoate groups, alteration of the structural and dynamical properties of the bilayer is expected to be governed by two different factors. First, the structural order of DPPC increases as surfactant aggregates interact with the membrane head group. Second, the decrease in the order of the bilayer occurs due to the insertion of surfactant monomers within the hydrophobic region of the bilayer. Strong interactions between constituents of tetraoctylammonium bromide (TOABr) and lipid head groups lead to a reduction in interlipid interactions and order, which further results in increased porosity of cellular membranes. Understanding the extent of these interactions plays a pivotal role in the toxicological assessment of these surfactants.

Project description:A series of double-chain quaternary ammonium salt surfactants N-[N'[3-(gluconamide)] propyl-N'-alkyl]propyl-N,N-dimethyl-N-alkyl ammonium bromide (CnDDGPB, where n represents a hydrocarbon chain length of 8, 10, 12, 14 and 16) were successfully synthesized from D (+)-glucose δ-lactone, N,N-dimethyldipropylenetriamine, and bromoalkane using a two-step method consisting of a proamine-ester reaction and postquaternization. Their surface activity, adsorption, and aggregation behavior in aqueous solution were investigated via measurements of dynamic/static surface tension, contact angle, dynamic light scattering, and transmission electron microscopy. An analysis of their application performance in terms of wettability, emulsifying properties, toxicity, and antibacterial properties was conducted. The results show that with increasing the carbon chain length of the CnDDGPB surfactants, their critical micelle concentration (CMC) increased and the pC20 and efficiency in the interface adsorption of the target product gradually decreased. Moreover, the influence of the hydrophobic carbon chain length on the surface of polytetrafluoroethylene (PTFE) was even greater for the wetting effect, reducing the contact angle to 32° within the length range of C8-C14. The results of the contact angle change and the wettability experiments proved that C10DDGPB exhibited the best wettability. The liquid paraffin and soybean oil emulsification ability of CnDDGPB showed an upward trend followed by a downward trend with the growth of the carbon chain, with C12DDGPB exhibiting the best emulsification performance. The Dlong/Dshort ratio was far lower than 1, which indicates mixed-kinetic adsorption. The surfactants formed spherical micelles and showed a unique aggregation behavior in aqueous solution, which showed an increase-decrease-increase trend with the change in concentration. A cell toxicity and acute oral toxicity experiment showed that the CnDDGPB surfactants were less toxic than the commonly used surfactant dodecyldimethylbenzyl ammonium chloride (1227). In addition, at a concentration of 150 ppm, CnDDGPB exhibited the same bacteriostatic effect as 1227 at a concentration of 100 ppm. The results demonstrate that sugar-based amide cationic surfactants are promising as environmentally friendly disinfection products.

Dataset Information

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

Publications

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

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