Vesicles from pH-regulated reversible gemini amino-acid surfactants as nanocapsules for delivery

Lv, Jing; Qiao, Weihong; Li, Zongshi

doi:10.1016/j.colsurfb.2016.06.054

Cited by 28 publications

(15 citation statements)

References 45 publications

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“…The reversible transition from micelles to other structures, especially to vesicles by changing pH, is very useful for drug delivery. Li et al showed that gemini amino acid surfactants, where pH is the key driving force to control the aggregation behaviours, can be applied to build colloidal systems for delivering hydrophobic drugs or nutrition [240].…”

Section: Drug Nanocarriersmentioning

confidence: 99%

Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications

Brycki¹,

Kowalczyk²,

Szulc³

et al. 2017

Application and Characterization of Surfactants

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Gemini cationic surfactants are compounds which are composed of two hydrophilic head groups and two hydrophobic tails linked by a spacer at the head groups or closed to them. The spacer can be either hydrophobic or hydrophilic. It can be rigid or flexible. The neutral charge of the molecule is retained by the presence of organic or inorganic counterions. Critical micelle concentrations (CMCs), surface tension (γ) and minimal inhibitory concentration (MIC) are dozen times lower than corresponding parameters of monomeric surfactants. The unique properties of gemini surfactants with a wide range of hydrophiliclipophilic balance (HLB) make them a very useful, innovative material in detergents, cosmetics, personal care products, additives for paints and coatings, biocides, material science, organic synthesis, pharmacy, textiles, enhanced oil recovery, nanotechnology, petroleum and many other branches of life. A large number of papers concerning gemini surfactants have been published so far. This review presents a synthetic look at current work devoted to structure, synthesis and applications of gemini surfactants.

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Section: Drug Nanocarriersmentioning

confidence: 99%

Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications

Brycki¹,

Kowalczyk²,

Szulc³

et al. 2017

Application and Characterization of Surfactants

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“…Moreover, these catanionic mixtures, depending on the surfactant mixing ratio and total concentration, form different micro- or nano-scale aggregates such us wormlike micelles, vesicles, cubic mesophases or lamellar phases [ 3 , 4 , 5 ]. Nowadays, to better control the self-assembly of these binary mixtures, new functional surfactants are developed [ 6 , 7 , 8 ]. The number of positive or negative charges in the polar head seriously affects the micellization process of single chain quaternary surfactants [ 9 , 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

“…2020, 21, 8912 2 of 22 or lamellar phases [3][4][5]. Nowadays, to better control the self-assembly of these binary mixtures, new functional surfactants are developed [6][7][8]. The number of positive or negative charges in the polar head seriously affects the micellization process of single chain quaternary surfactants [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Aggregation Behavior, Antibacterial Activity and Biocompatibility of Catanionic Assemblies Based on Amino Acid-Derived Surfactants

Pérez

Pinazo

Morán

2020

IJMS

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The surface activity, aggregates morphology, size and charge characteristics of binary catanionic mixtures containing a cationic amino acid-derived surfactant N(π), N(τ)-bis(methyl)-L-Histidine tetradecyl amide (DMHNHC14) and an anionic surfactant (the lysine-based surfactant Nα-lauroyl-Nεacetyl lysine (C12C3L) or sodium myristate) were investigated for the first time. The cationic surfactant has an acid proton which shows a strong pKa shift irrespective of aggregation. The resulting catanionic mixtures exhibited high surface activity and low critical aggregation concentration as compared with the pure constituents. Catanionic vesicles based on DMHNHC14/sodium myristate showed a monodisperse population of medium-size aggregates and good storage stability. According to Small-Angle X-Ray Scattering (SAXS), the characteristics of the bilayers did not depend strongly on the system composition for the positively charged vesicles. Negatively charged vesicles (cationic surfactant:myristate ratio below 1:2) had similar bilayer composition but tended to aggregate. The DMHNHC14-rich vesicles exhibited good antibacterial activity against Gram-positive bacteria and their bactericidal effectivity declined with the decrease of the cationic surfactant content in the mixtures. The hemolytic activity and cytotoxicity of these catanionic formulations against non-tumoral (3T3, HaCaT) and tumoral (HeLa, A431) cell lines also improved by increasing the ratio of cationic surfactant in the mixture. These results indicate that the biological activity of these systems is mainly governed by the cationic charge density, which can be modulated by changing the cationic/anionic surfactant ratio in the mixtures. Remarkably, the incorporation of cholesterol in those catanionic vesicles reduces their cytotoxicity and increases the safety of future biomedical applications of these systems.

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“…The surfactants which contain a hydrophobic group and four carboxyl groups were also prepared by the polyamine precursor (Sun, 2012). In addition, the Gemini surfactant with two hydrophobic alkyl chains and two hydrophilic carboxyl groups was synthesized by using ethylenediamine and sodium chloroacetate as raw materials (Lv et al, 2014, 2016; Rehman et al, 2017). In a similar way, the trimer surfactant with three hydrophobic chains and three hydrophilic carboxyl groups was prepared (Yoshimura et al, 2004; Zhou et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Two Amino Carboxylic Acid Gemini Surfactants

et al. 2020

J Surfact & Detergents

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The number of hydrophilic and hydrophobic groups of a surfactant has a great influence on its property. Two Gemini surfactants, N,N 00 '-didodecyl-N,N',N 00 ,N 00 'tetrapropionate triethylenetetramine and N,N'-didodecyl-N, N'-dipropionate ethylenediamine (referred as DTPTT and DDPED), were prepared by Michael addition reaction of the didodecyl secondary amines with methyl acrylate. The didodecyl secondary amines were synthesized by nucleophilic substitution reaction of triethylenetetramine or ethylenediamine with bromododecane. The DTPTT and DDPED surfactants were characterized by mass spectrometry and proton nuclear magnetic resonance spectrometry. The surface activities of the DTPTT and DDPED aqueous solutions were studied by surface tension measurements. The surface tension and critical micelle concentration (cmc) of DDPED is smaller than that of DTPTT. The DDPED can reduce the surface tension of water to approximate 34 mN m −1 at concentration levels of 10 −5 mol L −1. The aggregation behavior of the DTPTT and DDPED aqueous solution were studied by dynamic light scattering and transmission electron microscopy. Both surfactants can form spherical vesicles at a solution of about 3-5 times cmc of the Gemini surfactants. The foam property was determined by nitrogen blowing method. The DTPTT has relatively good foaming ability and DDPED has excellent foam stability. The foam volume of DDPED barely change within 1000s. The emulsion stability of the Gemini surfactants was determined by separation time of water from the emulsion. The emulsion stability of DDPED is equivalent to Tween 80. The DDPED Gemini surfactant with two hydrophilic carboxylic groups has better surface activity, foam stability, and can be used as an O/W emulsifier.

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Vesicles from pH-regulated reversible gemini amino-acid surfactants as nanocapsules for delivery

Cited by 28 publications

References 45 publications

Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications

Multifunctional Gemini Surfactants: Structure, Synthesis, Properties and Applications

Aggregation Behavior, Antibacterial Activity and Biocompatibility of Catanionic Assemblies Based on Amino Acid-Derived Surfactants

Synthesis and Properties of Two Amino Carboxylic Acid Gemini Surfactants

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