Aggregation behaviour and solubilization capability of mixed micellar systems formed by a gemini lipoamino acid and a non-ionic surfactant

Saavedra, Lucila; Gómez, Emma Laura Alfaro; Oliveira, Rafael G.; Fernández, Mariana A.

doi:10.1016/j.colsurfa.2017.08.011

Cited by 18 publications

(5 citation statements)

References 47 publications

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“…in the laboratory according to the literature [15] by the reaction of cystine with decanoic chloride as described previously [25]. Water was MilliQ quality obtained from a Millipore instrument (resistivity, 25°C: 18 M cm).…”

Section: Reactantsmentioning

confidence: 99%

“…We performed the synthesis of AgNP using SDDC above its critical micelle concentration in water (cmc: 0.28 mM at pH 7.00; 0.35 mM at pH 9.16) [25] to act as both a template and stabilizer, maintaining a molar ratio Ag + : SDDC equal to 1:10. This ratio was chosen on basis to previous experiments performed in our laboratory to find optimal conditions for the study of the interaction of cations with Gemini surfactants.…”

Section: Synthesis and Characterization Of Agnp@sddcmentioning

confidence: 99%

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Role of a cystine-based Gemini surfactant ligand in the synthesis of catalytic active silver nanoparticles

Torres

Gómez

Fernández

et al. 2019

Journal of Molecular Liquids

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We report the synthesis in water of colloidal silver nanoparticles (AgNP) using a Gemini lipoamino acid surfactant derived from cysteine as a capping agent. The Gemini surfactant interacts with the metal surface mainly in a monodentate vertical mode through the carboxylate group preserving intact the disulfide bond. These nanoparticles present catalytic activity to the reduction of pnitrophenol, and the synthesis of AgNP under mild reduction conditions maintaining the seeds size. Also, the Gemini surfactant leads to anisotropic morphologies in the seed-mediated growth of AgNP@citrate seeds aided by the presence of bromide ions.

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Section: Reactantsmentioning

confidence: 99%

Section: Synthesis and Characterization Of Agnp@sddcmentioning

confidence: 99%

Role of a cystine-based Gemini surfactant ligand in the synthesis of catalytic active silver nanoparticles

Torres

Gómez

Fernández

et al. 2019

Journal of Molecular Liquids

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“…It is considered to be much safer compared with traditional surfactants. In addition, LAA also has a high surface activity, bacteriostasis, and low toxicity, which make it extremely valuable in food, personal care, and biological fields. , Despite their attractiveness, LAA can hardly be utilized on an industrial scale. In previous studies, LAA were mostly synthesized by organic synthesis, which could cause large amounts of byproducts and environmental problems and can hardly be considered as “green” .…”

Section: Introductionmentioning

confidence: 99%

Lipase and Metal Chloride Hydrate-Natural Deep Eutectic Solvents Synergistically Catalyze Amidation Reaction via Multiple Noncovalent Bond Interactions

Nian

Cao

Liu

2019

ACS Sustainable Chem. Eng.

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With their extreme advantages in high surface activity, bacteriostasis, and low toxicity, lipoamino acids (LAA) attracted widespread academic and industrial interests. In this study, natural deep eutectic solvents (NADESs), were adopted as a medium of enzymatic synthesis of lauroyl glycine (LG). The highest yield of 50.49 ± 1.94% was obtained in the C-Gly system. Interestingly, a synergistic effect between CALB and NADESs was found in this section. We proposed that anions play a key role in this process. To explore it, metal chloride hydrates were added into C-Gly. Fortunately, seven kinds of three-constituent NADESs (3c-NADESs) with a low viscosity were successfully formed. All of these new-design solvents were used as a medium of enzymatic of LG, and the highest yield of LG can reach 85.97 ± 1.86% after optimization. To explore the mechanism of the synergistic effect between CALB and 3c-NADESs. The results of molecular dynamics studies (MD) showed that there was no significant change of CALB in this process, which indicated that CALB may play a secondary role in the synergistic effect. In this context, we studied the molecular interaction between Mg-CGly and lauric acid, and the reaction processes were studied in depth via IRC method. The results suggested that a strong H-bond was formed between Cl– and lauric acid. This interaction may increase the electron-attracting ability of fatty acids and make them more susceptible to be attacked by amino acids and thus to increase the yield of amidation reaction of lauric acid and glycine.

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“…Lipoamino acids (LAA), also known as N -acyl amino acids, are composed of natural fatty acids and amino acids by acylation reaction, which was considered to be much safer and greener compared with traditional surfactants. , As an alternative to petrochemical-based amphiphiles, LAA are extremely advantageous in terms of sustainability, biocompatibility, biodegradability, and bacteriostasis, which make them exceedingly potentially valuable in the food, biological, and personal care fields. − For instance, Burstein argued that a kind of N -acyl amino acids, namely elmiric acid was an endogenous signaling molecule with therapeutic potential . Besides, seven LAA were synthesized by Kaki et al., and an equal antimicrobial activity to Gram-positive bacteria with miconazole was obtained in oleoylalanine .…”

mentioning

confidence: 99%

“…argued that the critical micelle concentration value of GLAA can be one or even orders of magnitude lower than that of single-chain surfactants . It can be attributed to chemical bonds between the head groups of GLAA which can evidently reduce the electrostatic repulsion between them, thereby increasing the surface activity . Moreover, a series of novel l -lysine-based gemini surfactants were synthesized by Xiao et al, and better antibacterial activity was found in broad spectrum of Gram-positive and Gram negative bacteria compared with SLAA …”

mentioning

confidence: 99%

Synergistic Catalytic Synthesis of Gemini Lipoamino Acids Based on Multiple Hydrogen-Bonding Interactions in Natural Deep Eutectic Solvents-Enzyme System

Nian¹,

Cao²

2020

J. Agric. Food Chem.

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In the previous studies, gemini lipoamino acids (GLAA) were always synthesized by complex multistep organic synthesis, which involved a large number of byproducts and organic solvents. To develop a straightforward, efficient, and renewable synthesis strategy for GLAA, in this study, a type of novel green solvents, natural deep eutectic solvents (NADESs), were adopted as the solvents for these reactions. Five commercial enzymes were involved in the enzyme screening section, and Candida antarctica lipase B (CALB) tended to have the best performance in NADESs systems. The optimization procedure was performed using the Taguchi crossed array method and the highest yield of GLAA (59.14 ± 0.51%) was obtained in choline chloride–glycerol (C–Gly). The purification procedure was carried out with ethyl acetate and water, and the isolate yield ranged from 86.31 ± 2.36 to 91.34 ± 2.26%. With 10 times recycling, the yield of GLAA in C–Gly decreased from 59.14 ± 0.51 to 51.31 ± 0.68%. Interestingly, a synergistic effect of CALB and NADESs was found in the enzymatic synthesis of GLAA, which can be attributed to fatty acids being activated by chloride ions via hydrogen-bonding interactions and resulting in an enhancement in its electron-attracting ability.

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Aggregation behaviour and solubilization capability of mixed micellar systems formed by a gemini lipoamino acid and a non-ionic surfactant

Cited by 18 publications

References 47 publications

Role of a cystine-based Gemini surfactant ligand in the synthesis of catalytic active silver nanoparticles

Role of a cystine-based Gemini surfactant ligand in the synthesis of catalytic active silver nanoparticles

Lipase and Metal Chloride Hydrate-Natural Deep Eutectic Solvents Synergistically Catalyze Amidation Reaction via Multiple Noncovalent Bond Interactions

Synergistic Catalytic Synthesis of Gemini Lipoamino Acids Based on Multiple Hydrogen-Bonding Interactions in Natural Deep Eutectic Solvents-Enzyme System

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