Non-conventional surfactants from amino acids and glycolipids: Structure, preparation and properties

Infante, M. R.; Pinazo, Aurora; Seguer, J.

doi:10.1016/s0927-7757(96)03793-4

Cited by 116 publications

(115 citation statements)

References 78 publications

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“…1); its synthesis and physiochemical properties can be found in the literature [21,23,24]. Double stranded DNA (dsDNA) type XIV from herring testes and T2 DNA were purchased from Sigma and used as received.…”

Section: Methodsmentioning

confidence: 99%

The association of DNA and stable catanionic amino acid-based vesicles

Rosa

Morán

Miguel

et al. 2007

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Cationic surfactants associate strongly to DNA and compact but are often toxic. The interaction of some novel cationic amino acid-based surfactants, which may enhance transfection and appear to be nontoxic, is described. A cationic arginine-based surfactant, ALA, gives in combination with anionic surfactants spontaneously stable vesicles, and special attention is given to the association of these catanionic vesicles, with a net positive charge, to DNA. The ability of this surfactant alone to compact DNA is compared in fluorescence microscopy studies to classical cationic surfactants. Addition of DNA to a solution of the catanionic vesicles results in associative phase separation at very low vesicle concentrations; there is a separation into a precipitate and a supernatant solution, which is first bluish but becomes clearer as more DNA is added. From studies using cryogenic transmission electron microscopy (cryo-TEM) and small angle X-ray scattering it is demonstrated that there is a lamellar structure with DNA arranged within the surfactant bilayers. Analysis of the supernatant by means of proton nuclear magnetic resonance ( 1 H NMR) showed that above the isoelectric point between ALA, anionic surfactant (sodium octyl sulfate, SOS) and DNA, anionic surfactant starts to be expelled from the bilayers on further incorporation of DNA. There appears to be a transition from a lamellar to a hexagonal liquid crystal structure when most of SOS has been expelled from the aggregate bilayers; at higher DNA-to-surfactant ratios, self-assembled SOS micelles and the excess of DNA added seem to coexist in solution. Regarding the phase-separating DNA-surfactant particles, cryo-TEM demonstrates a large and nonmonotonic variation of particle size as the DNA-surfactant ratio is varied, with the largest particles obtained in the vicinity of overall charge neutrality.

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Section: Methodsmentioning

confidence: 99%

The association of DNA and stable catanionic amino acid-based vesicles

Rosa

Morán

Miguel

et al. 2007

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…nonionic, mono/di, ester, nonionic, mono, ester, nonionic, di, ester, nonionic, mono, ester, (Kitamoto et al 2009) nonionic, di, ester, (Infante et al 1997)…”

Section: Low Molecular Massunclassified

Carbohydrate-Based Surfactants: Structure-Activity Relationships

Razafindralambo¹,

Blecker²,

Paquot³

2012

Advances in Chemical Engineering

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“…Regarding arginine-N-lauroyl amide dihydrochloride (ALA) and N R -lauroyl-arginine-methyl ester hydrochloride (LAM), their synthesis and physicochemical properties can be found in the literature. 38,41,42 ALA and HS have two charges in the headgroup, positive and negative, respectively. All concentrations are presented per charge.…”

Section: Methodsmentioning

confidence: 99%

Spontaneous Formation of Vesicles and Dispersed Cubic and Hexagonal Particles in Amino Acid-Based Catanionic Surfactant Systems

et al. 2006

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Mixed catanionic surfactant systems based on amino acids were investigated with respect to the formation of liquid crystal dispersions and the stability of the dispersions. The surfactants used were arginine-N-lauroyl amide dihydrochloride (ALA) and N R -lauroyl-arginine-methyl ester hydrochloride (LAM), which are arginine-based cationic surfactants; sodium hydrogenated tallow glutamate (HS), a glutamic-based anionic surfactant; and the anionic surfactants sodium octyl sulfate (SOS) and sodium cetyl sulfate (SCS). It is demonstrated that in certain ranges of composition there is a spontaneous formation of vesicular, cubic, and hexagonal structures. The solutions were characterized with respect to internal structure and size by cryogenic transmission electron microscopy (cryo-TEM), dynamic light scattering (DLS), and turbidity measurements. Vesicles formed spontaneously and were found for all systems studied; their size distribution is presented for the systems ALA/SCS/W and ALA/SOS/W; they are all markedly polydisperse. The aging process for the system ALA/SOS/W was monitored both by turbidity and by cryo-TEM imaging; the size distribution profile for the system becomes narrower and the number average radius decreases with time. The presence of dispersed particles with internal cubic structure (cubosomes) and internal hexagonal structure (hexosomes) was documented for the systems containing ALA and HS. The particles formed spontaneously and remained stably dispersed in solution; no stabilizer was required. (Cubosome and hexosome are USPTO registered trademarks of Camurus AB, Sweden.) The spontaneous formation of particles and their stability, together with favorable biological responses, suggests a number of applications.

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Non-conventional surfactants from amino acids and glycolipids: Structure, preparation and properties

Cited by 116 publications

References 78 publications

The association of DNA and stable catanionic amino acid-based vesicles

The association of DNA and stable catanionic amino acid-based vesicles

Carbohydrate-Based Surfactants: Structure-Activity Relationships

Spontaneous Formation of Vesicles and Dispersed Cubic and Hexagonal Particles in Amino Acid-Based Catanionic Surfactant Systems

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