Chemical Structure/Property Relationship in Single-Chain Arginine Surfactants

Morán, Carmen; Clapés, Pere; Comelles, F.; García, T. Viveros; Pérez, Lourdes; Vinardell, M. Pilar; Mitjans, Montserrat; Infante, M. R.

doi:10.1021/la010375d

Cited by 101 publications

(94 citation statements)

References 17 publications

(35 reference statements)

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“…Regarding these surfactants, a systematic study on their antimicrobial properties with different tail length was previously reported. 5 This study showed that the efficiency of singlechain surfactants is affected by their alkyl chain length, with a maximum effect for the 12 carbon tail surfactants. Over the past decade, developments on enzyme technology in non-conventional media have opened new possibilities for the synthesis of surfactants from natural sources.…”

Section: Introductionmentioning

confidence: 78%

Interaction of arginine-based cationic surfactants with membranes. An experimental and molecular simulation study

Almeida¹,

Morán²,

Infante³

et al. 2009

Arkivoc

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This work is dedicated to Prof. António M. d'A. Rocha Gonçalves, on the occasion of his 70 th birthday: to the teacher, scientist and academic AbstractThe effect of two arginine-based cationic surfactants, arginine N-lauroyl amide dihydrochloride and arginine O-lauroyl ester dihydrochloride, upon dipalmitoylphosphatidylcholine liposomes, is addressed in this work. Some aspects concerning the synthesis of these surfactants are also presented in some detail. Differential scanning calorimetry, as well as fluorescence anisotropy using several probes, is used to assess the relative effects on the lipid model membranes. In spite of the structural similarity among these molecules, which differ only by the group that connects the polar head to the tail, experimental results suggest differences in their behavior. Molecular dynamics simulation provides significant insight into the molecular mechanism that governs this interaction. A rationale is provided in terms of lipid-surfactant hydrogen bonding and the consequent positioning of the surfactant molecule within the bilayer.

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Section: Introductionmentioning

confidence: 78%

Interaction of arginine-based cationic surfactants with membranes. An experimental and molecular simulation study

Almeida¹,

Morán²,

Infante³

et al. 2009

Arkivoc

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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%

“…It was found that it, in analogy with several other mixed cationic-anionic surfactant systems, presents a spontaneous formation of vesicles having a long-term stability; in fact they remain over our extended times of investigation suggesting that they may be thermodynamically stable. Our approach of using an amino acid-based single-tailed surfactant in the catanionic vesicle composition was based on the fact that ALA alone and the mixture of ALA and SOS presented cell viability percentages above 90% (results to be published); ALA has also been reported as being biodegradable [21].…”

Section: Dna Addition To the Vesicle Systemmentioning

confidence: 99%

“…Since one of our main motivations consists in the development of new non-toxic biocompatible and biodegradable [21] systems, we introduced in this study an amino acid-based cationic surfactant, ALA, with an arginine head-group. Furthermore, toxicity studies (data to be published elsewhere) revealed that the incorporation of ALA in our catanionic vesicles system transformed them into cell viable systems, extending therefore their use to drug and gene delivery systems, as well as cosmetic and food formulations [22].…”

Section: Introductionmentioning

confidence: 99%

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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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“…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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Chemical Structure/Property Relationship in Single-Chain Arginine Surfactants

Cited by 101 publications

References 17 publications

Interaction of arginine-based cationic surfactants with membranes. An experimental and molecular simulation study

Interaction of arginine-based cationic surfactants with membranes. An experimental and molecular simulation study

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

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

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