Green cationic arginine surfactants: Influence of the polar head cationic character on the self-aggregation and biological properties

Pérez, Lourdes; Sousa, Francisco Fábio Oliveira de; Morán, María del Carmen; Silva, Anderson Ramos da; Pinazo, Aurora

doi:10.1016/j.molliq.2021.116819

Cited by 21 publications

(7 citation statements)

References 55 publications

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“…Cationic surfactants present remarkable antimicrobial properties. Despite their great bioactivity [ 1 , 2 , 3 ], they are the most irritative category to skin and mucous tissues, what limits their clinical applicability [ 4 ]. Among the multifunctional compounds, amino acid-based surfactants represent great potential.…”

Section: Introductionmentioning

confidence: 99%

Zein Nanoparticles Containing Arginine-Phenylalanine-Based Surfactants: Stability, Antimicrobial and Hemolytic Activity

et al. 2023

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Although cationic surfactants have a remarkable antimicrobial activity, they present an intrinsic toxicity that discourages their usage. In this work novel zein nanoparticles loaded with arginine-phenylalanine-based surfactants are presented. The nanoparticles were loaded with two single polar head (LAM and PNHC12) and two with double amino acid polar head surfactants, arginine-phenylalanine (C12PAM, PANHC12). The formulations were characterized and their stability checked up to 365 days. Furthermore, the antimicrobial and hemolytic activities were investigated. Finally, NMR and molecular docking studies were carried out to elucidate the possible interaction mechanisms of surfactant-zein. The nanoparticles were obtained with satisfactory size, zeta potential and dispersibility. The surfactants containing arginine-phenylalanine residues were found to be more stable. The nanoencapsulation maintained the antimicrobial activities unaltered in comparison to the surfactants’ solutions. These results are in agreement with the NMR and docking findings, suggesting that zein interacts with the surfactants by the aromatic rings of phenylalanine. As a result, the cationic charges and part of the aliphatic chains are freely available to attack the bacteria and fungi, while not available to disrupt the cellular membranes. This approach opens new possibilities for using cationic surfactants and benefits from their extraordinary antimicrobial responses for several applications.

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Section: Introductionmentioning

confidence: 99%

Zein Nanoparticles Containing Arginine-Phenylalanine-Based Surfactants: Stability, Antimicrobial and Hemolytic Activity

et al. 2023

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“…Therefore, those authors classi ed the arginine-based surfactants studied in their work as fungicidal compounds; on the basis of this concept, Bz-Arg-NHC 10 can be included within this group. The results reported by those authors also suggested an antagonistic effect of the amino and guanidinium groups on the antifungal behavior of the arginine-based tensioactives studied: therefore, the presence of the amino group may partially neutralize the anticandida action of the guanidinium group(Pérez et al 2021). This effect seemed to be compensated in the example of our compounds, since the benzoyl group attached to the amino-acid moiety increases the molecule's hydrophobicity(Hermet et al 2021).…”

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confidence: 83%

“…Regarding the previously reported in uence of the length of the surfactant's alkyl moiety (Tot et al 2022)-i.e., the longer the alkyl moiety, the more biocidal the effect-twelve-carbon analogues were more e cient against C. albicans than those bearing alkyl moieties with ten carbons among the AAM and AAA series of surfactants(Morán et al 2001). No clear tendency had been found, however, for Bz-Arg-NHC n in this regard.According toPérez et al (2021), compounds with MFC values equal to or twice their MIC values can be listed as fungicidal agents. Therefore, those authors classi ed the arginine-based surfactants studied in their work as fungicidal compounds; on the basis of this concept, Bz-Arg-NHC 10 can be included within this group.…”

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confidence: 99%

Candidicidal Effect of Arginine-based Surfactants

Fait¹,

Grillo²,

Garrote

et al. 2023

Preprint

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Amino-acid–based surfactants are a group of compounds that resemble natural amphiphiles and thus are expected to have a low impact on the environment, owing to either the mode of surfactant production or its means of disposal. Within this context, arginine-based tensioactives have gained particular interest since their cationic nature—in combination with their amphiphilic character—enables them to act as broad-spectrum biocides. This capability is based mainly on their interactive affinity for the microbial envelope that alters the latter’s structure and ultimately its function. In the work reported here, we investigated the efficiency of Nα-benzoyl arginine decyl- and dodecylamide against Candida spp. to further our understanding of the antifungal mechanism involved. For the assays, both a Candida albicans and a Candida tropicalis clinical isolates along with a C. albicans–collection strain were used as references. As expected, both arginine-based compounds proved to be effective against the strains tested through inhibiting both the planktonic and the sessile growth. Furthermore, atomic-force–microscopy techniques and lipid-monolayer experiments enabled us to gain insight into the effect of the surfactant on the cellular envelope. The results demonstrated that all the yeasts treated exhibited changes in their exomorphologic structure, with respect to alterations in both roughness and stiffness, relative to the nontreated ones. This finding—in addition to the amphiphiles’ proven ability to insert themselves within this model fungal membrane—could explain the changes in the yeast-membrane permeability that could be linked to viability loss and mixed-vesicle release.

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“…Moreover, the CMC increases with the increasing size of the hydrophilic group, which is mainly due to steric hindrance [18,[24][25][26][27]. Generally, surfactants are divided into ionic (cationic or anionic), nonionic, or zwitterionic surfactants based on the charge of their polar head group [28]. Many studies have shown that nonionic surfactants are preferable to ionic surfactants in soil remediation [29], due to the adsorption of cationic surfactants [29] or precipitation of anionic surfactants [30] with some counterions.…”

Section: Introductionmentioning

confidence: 99%

Synthetic and Natural Surfactants for Potential Application in Mobilization of Organic Contaminants: Characterization and Batch Study

Amanat

Barbati

Rossi

et al. 2022

Water

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In this paper, we investigated the abilities of five sugar-based synthetic surfactants and biosurfactants from three different families (i.e., alkyl polyglycoside (APG), sophorolipid (SL), and rhamnolipid (RL)) to dissolve and mobilize non-aqueous phase liquid (NAPL) components, i.e., toluene and perchloroethylene (PCE), adsorbed on porous matrices. The objective of this study was to establish a benchmark for the selection of suitable surfactants for the flushing aquifer remediation technique. The study involved a physicochemical characterization of the surfactants to determine the critical micelle concentration (CMCs) and interfacial properties. Subsequently, a batch study, through the construction of adsorption isotherms, made it possible to evaluate the surfactants’ capacities in contaminant mobilization via the reduction of their adsorptions onto a reference adsorbent material, a pine wood biochar (PWB). The results indicate that a synthetic surfactant from the APG family with a long fatty acid chain and a di-rhamnolipid biosurfactant with a shorter hydrophobic group offered the highest efficiency values; they reduced water surface tension by up to 54.7% and 52%, respectively. These two surfactants had very low critical micelle concentrations (CMCs), 0.0071 wt% and 0.0173 wt%, respectively; this is critical from an economical point of view. The batch experiments showed that these two surfactants, at concentrations just five times their CMCs, were able to reduce the adsorption of toluene on PWB by up to 74% and 65%, and of PCE with APG and RL by up to 65% and 86%, respectively. In general, these results clearly suggest the possibility of using these two surfactants in surfactant-enhanced aquifer remediation technology.

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Green cationic arginine surfactants: Influence of the polar head cationic character on the self-aggregation and biological properties

Cited by 21 publications

References 55 publications

Zein Nanoparticles Containing Arginine-Phenylalanine-Based Surfactants: Stability, Antimicrobial and Hemolytic Activity

Zein Nanoparticles Containing Arginine-Phenylalanine-Based Surfactants: Stability, Antimicrobial and Hemolytic Activity

Candidicidal Effect of Arginine-based Surfactants

Synthetic and Natural Surfactants for Potential Application in Mobilization of Organic Contaminants: Characterization and Batch Study

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