Amino acid–based surfactants: New antimicrobial agents

Pinazo, Aurora; Manresa, Maria Àngels; Marqués, Ana; Bustelo, M.; Espuny, M. J.; Pérez, Lourdes

doi:10.1016/j.cis.2015.11.007

Cited by 174 publications

(143 citation statements)

References 99 publications

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“…In addition, the atoms in functional groups, like the amide bond found in amino acid-based surfactants, often form intermolecular hydrogen bonds that in turn play an important role in determining the size and shape of surfactant micelles [11][12][13]. Amino acid-based surfactants have become increasingly popular in recent years because they are environmentally benign, abundant, and quite versatile [11][12][13][14][15][16][17][18][19]. Surfactants with amino acid head groups have both amide and carboxylic acid functional groups; therefore, solution pH would be expected to affect the percentage ionization of the carboxylate groups and the rate at which amide protons exchange with solvent [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l‐Undecyl Leucinate Micelles

Lewis

Hughes

Vasquez

et al. 2016

J Surfact & Detergents

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Micelle formation by the amino acid‐based surfactant undecylenyl l‐leucine was investigated as a function of solution pH with NMR, dynamic light scattering, and fluorescence spectroscopy. NMR and dynamic light scattering showed that 50 mM undecylenyl l‐leucine and 50 mM NaHCO3 solutions contained micelles approximately 20 Å in diameter and that micelle radius and the mole fraction of surfactant molecules associated with micelles changed very little with solution pH. The binding of the amino acids arginine and lysine to the anionic micelles was also investigated from pH 7.0 to 11.5. Below pH 9.0, the mole fraction of arginine cations bound to the micelles was approximately 0.4. Above pH 9.0, the arginine counterions became zwitterionic, and the mole fraction of bound arginine molecules decreased steadily to less than 0.1 at pH 11. When arginine dissociated from the micelles, their radii decreased from 14 to 10 Å. Similar behavior was observed with lysine; however, when lysine dissociated from the micelle surface, little change in micelle radius was observed. Two‐dimensional NMR experiments suggested that below pH 9.0, l‐arginine bound perpendicular to the micelle surface primarily though its side chain amine while l‐lysine bound parallel to the surface through both of its amine functional groups. Finally, the rate at which the amide protons on the surfactant headgoup exchanged with solvent was investigated with NMR spectroscopy. The exchange reaction was faster in solutions containing only surfactant monomers and slower when the surfactants were in micellar form and the headgoup amide protons were less exposed to solvent.

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Section: Introductionmentioning

confidence: 99%

Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l‐Undecyl Leucinate Micelles

Lewis

Hughes

Vasquez

et al. 2016

J Surfact & Detergents

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“…In all instances, 20 ml of the corresponding surfactant solution was spotted on freshly cleaved planchets of muscovite mica. Samples for studies in air were dried under N 2 where OD c is the optical density of control erythrocytes (PBS buffer), OD x is the optical density of erythrocytes treated with different concentrations of the surfactants, and OD tx is the optical density of erythrocytes incubated in the presence of 1% (v/v) Triton X-100 (to produce 100% hemolysis). Dose-response curves were constructed by plotting the percent hemolysis vs. the surfactant concentration for each hematocrit.…”

Section: Atomic-force Microscopy (Afm)mentioning

confidence: 99%

Microvesicle release and micellar attack as the alternative mechanisms involved in the red-blood-cell-membrane solubilization induced by arginine-based surfactants

et al. 2017

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Two novel arginine-based surfactants, Bz-Arg-NHC 10 and Bz-Arg-NHC 12 , were characterized with respect to surface properties and their interaction with human red-blood-cell (HRBC) membranes. The values for critical micellar concentration (CMC), the maximum surfactant adsorption at the air-liquid interface, and the area per molecule indicated better surface properties for Bz-Arg-NHC 12 . The observation of cylindrical worm-like aggregates of Bz-Arg-NHC n via atomic-force microscopy supported the predictions based on the value of the surfactant-packing parameter (SPP). Erythrocyte-membrane solubilization was effected by surfactant aggregates since cell lysis became evident at only surfactant concentrations above the CMC. Changes in HRBC shape observed at different surfactant concentrations led to the conclusion that a slow mechanism based on the insertion of surfactant monomers into the HRBC membrane, followed by a shedding of microvesicles was responsible for the hemolysis produced by both surfactants at the lower concentrations tested. In contrast, the extraction of membrane lipids upon collisions between HRBCs and surfactant aggregates competes with and prevents microvesicle release at the higher concentrations assayed.

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“…In general, amino-acid derivatives are considered as biocompatible surfactants, which make them highly suitable for use as emulsifiers, detergents, wetting agents, foaming, dispersing compounds, or antimicrobial agents. Several recent reviews focused on the synthesis and properties of amino acid-based surfactants (Bordes and Holmberg, 2015;Morán et al, 2004;Pinazo et al, 2011Pinazo et al, , 2016.…”

Section: Amino Acid As a Polar Head Groupmentioning

confidence: 99%

Renewable Surfactants for Biochemical Applications and Nanotechnology

Guenic

Chaveriat

Lequart

et al. 2018

J Surfact & Detergents

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Surfactants find applications in almost every chemical industry, such as household and industrial cleaning, paper, inks, agrochemicals, and personal care or pharmaceuticals. However, their production and use can have a negative impact on the environment and health. Increasing environmental concerns and the strong interest in renewable resources have led to the development of innovative and environmentally friendly surfactants produced by clean and/or sustainable technologies. The aim of this review is to explore the different types of surfactants and their architectures. Then, it will describe the two categories of renewable surfactants: biosurfactants obtained by fermentation, and bio‐based surfactants containing either a bio‐sourced polar head group or a bio‐sourced hydrophobic tail. Finally, this review will focus on highly specialized applications of surfactants (protein crystallization, transfection, and nanotechnology), which are closely related to the ability of surfactants to organize themselves in supramolecular architectures.

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Amino acid–based surfactants: New antimicrobial agents

Cited by 174 publications

References 99 publications

Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l‐Undecyl Leucinate Micelles

Effect of pH on the Binding of Sodium, Lysine, and Arginine Counterions to l‐Undecyl Leucinate Micelles

Microvesicle release and micellar attack as the alternative mechanisms involved in the red-blood-cell-membrane solubilization induced by arginine-based surfactants

Renewable Surfactants for Biochemical Applications and Nanotechnology

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