Gemini surfactants from natural amino acids

Pérez, Lourdes; Pinazo, Aurora; Pons, Ramón; Infante, M. R.

doi:10.1016/j.cis.2013.10.020

Cited by 152 publications

(110 citation statements)

References 137 publications

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“…All the compounds tested formed lipoplexes but at different N/P ratios. The number of cationic nitrogen of gemini required per phosphorous residue of pDNA (i.e., N/P ratio) for complete complexation was found to be close to 4.8 and 9.6 for AG2-C 12 and AG2-C 14 , respectively, and 2.4 for AG2-C 16 and AG2-C 18 , which is comparable to other cationic amphiphiles with excellent gene transfection ability [15]. During gel electrophoresis, fluorescent dye bands were present with equal intensity within the N/P ratios 0 -0.6 for all the AG2-C n , which indicates no prominent binding with pDNA.…”

Section: Dna Binding Assaymentioning

confidence: 99%

“…Secondly, the lipophilic acid (lauric, myristic, palmitic and oleic) was attached to the N-terminus of a resin-bound peptide using the same synthesis method as for AG2 to obtain AG2-C 12 ; AG2-C 14 ; AG2-C 16 and AG2-C 18 , respectively (Table 1). Rink amide 4-Methylbenzy-drylamine resin (MBHA) was used to prepare the C-terminal peptide amide.…”

Section: Synthesis and Characterization Of Monomeric Amphiphilesmentioning

confidence: 99%

“…One of the methods most commonly used for the synthesis of amphiphilic amino acid derivatives is the peptide N-terminal acylation [16]. If the peptide has cysteine in its sequence, it may dimerize by oxidative coupling obtaining the corresponding gemini [17] [18] [19] [20].…”

mentioning

confidence: 99%

“…Several classes of natural amino acid-based gemini have been synthesized and characterized for the purpose of gene delivery [13] [14] [15] [16]. One of the methods most commonly used for the synthesis of amphiphilic amino acid derivatives is the peptide N-terminal acylation [16].…”

mentioning

confidence: 99%

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New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection <i>in Vitro</i>

Peña¹,

Argarañá²,

Zan³

et al. 2017

ACES

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Nucleic acids-based therapies have recently developed as next-generation agents for treating and preventing viral infection, cancer, and genetic disorders, but their use is still limited due to its relatively poor delivery into targeted cells. We designed and synthesized new amphiphilic amino acid derivatives (cysteine-based) of low molecular weight, formed by the same pentapeptide (AG2: WWCOO) N-acylated, with different hydrophobic chains containing from 12 to 18 carbons, named AG2-C n (N), which dimerize by oxidation in the presence of pLenti-CMV-GFP Puro plasmid (P) in the respective gemini. We determined transfection efficiency, critical micelle concentration, particle size, ζ-potential and cytotoxicity for the derivatives obtained. We found that all the synthesized compounds were active for DNA delivery and had greater ability to transfect CHO-K1 cells. In particular, AG2-C 18 is a promising carrier for gene delivery because it showed no cytotoxicity and its activity was greater than or equal to the commercial actives currently used.

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Section: Dna Binding Assaymentioning

confidence: 99%

Section: Synthesis and Characterization Of Monomeric Amphiphilesmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection <i>in Vitro</i>

Peña¹,

Argarañá²,

Zan³

et al. 2017

ACES

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“…Obviously, the CMC values are dependent on the chemical structure of the surfactant molecules [34]. The different CMC values of this surfactant depend on the hydrophobic moieties in its structure.…”

Section: Surface Activitymentioning

confidence: 99%

Biocidal activity and corrosion inhibition of some cationic surfactants derived from Thiol polyurethane.

Zaky

Sabbah²,

Negm

et al. 2017

Egypt. J. Chem.

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SIX series of cationic polyurethane surfactants were synthesized by the reaction between different six esters (which prepared by condensation of fatty alcohols namely: octanol, decanol, dodecanol, tetradecanol, hexadecanol and octadecanol with bromoacetic acid) and polyurethane as quaternizing agent. The chemical structures of these surfactants were confirmed using elemental analysis, FTIR spectra, + HNMR and UV analysis. The surface activities of the synthesized cationic thiol polyurethane surfactants showed their tendency towards adsorption at the air/water interface. The adsorption tendency was estimated from the values of surface tension and the depression of surface tension at the critical micelle concentration. The studied surfactants were evaluated as antimicrobial agents against pathogenic and sulfur reducing bacteria using inhibition zone diameters and minimum inhibition concentration values. The synthesized cationic thiol polyurethane surfactants showed good antimicrobial activities against the tested microorganisms including Gram positive, Gram negative as well as fungi. The synthesized compounds were tested for the activity as corrosion inhibitors against carbon steel corrosion in 2N H 2 SO 4 at 50, 100, 200, 400 and 600 ppm. The inhibition efficiencies of the tested compounds showed good inhibition and protection of the carbon steel. The corrosion inhibition tendency correlated to the surface activity and chemical structure of the compounds.Keywords: Cationic surfactants, Surface activity, Adsorption , Antimicrobial activity, Corrosion inhibition, Polyurethane. IntoductionCorrosion inhibitors are added to prevent metal dissolution during its surface cleaning from oxides and other adherent materials [1]. Also, corrosion inhibitors may be liquids or powder form that effectively reduces the corrosion rate by adsorbing on the metal surface [2,3]. Corrosion inhibition efficiency of organic compounds is related to their adsorption properties [4]. Corrosion protection of steel in acidic media is of great importance for both industrial facilities and theoretical aspects [5]. The adsorption of these molecules depends mainly on certain physicochemical properties of the inhibitor molecule such as the presence of heteroatoms including: oxygen, sulfur, nitrogen atoms and multiple bonds in the molecule through which they are adsorbed on the metal surface [6][7][8][9][10].Heteroatoms such as nitrogen, oxygen, and sulfur are capable of forming coordinate covalent bond with metal owing to their free electron pairs and thus acting as inhibitor. Compounds with π bonds generally exhibit good inhibitive properties due to the interaction of π orbital with metal surface [11][12][13]. The selection of a suitable inhibitor for a particular system is a difficult task because of the selectivity of the inhibitors and wide variety of corrosive environment. As a result, several types of corrosion inhibitors were developed to fit the different types of corrosion processes and also the medium where the corrosion takes place. Cor...

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Sustainable Surfactants Based on Amino Acids

Pérez

Infante

Pinazo

2016

Encyclopedia of Inorganic and Bioinorganic Chemistry

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Surfactants are chemical products consumed in large quantities every day on a worldwide scale. In recent years, environmental concerns and regulatory pressure have emerged as the driving forces to partly replace petrochemical‐based surfactants with those based on naturally occurring renewable sources. The hope that such surfactants would be biodegradable and biocompatible has provided strong incentive for the research of less irritant and less toxic consumer‐friendly surfactants. Biodegradability, low toxicity, and antimicrobial activity are properties common to surfactants derived from amino acids. In this chapter we offer an overview of the synthesis methods and properties published in the literature concerning four families of amino acid based surfactants: single chain, amino acid based surfactants, diacyl‐glycerolipid conjugates, gemini surfactants from amino acids, and polydispersed lipopeptides from a mixture of amino acids. Whenever present in the source material, specific applications are described.

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Gemini surfactants from natural amino acids

Cited by 152 publications

References 137 publications

New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection <i>in Vitro</i>

New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection <i>in Vitro</i>

Biocidal activity and corrosion inhibition of some cationic surfactants derived from Thiol polyurethane.

Sustainable Surfactants Based on Amino Acids

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Gemini surfactants from natural amino acids

Cited by 152 publications

References 137 publications

New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection &lt;i&gt;in Vitro&lt;/i&gt;

New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection &lt;i&gt;in Vitro&lt;/i&gt;

Biocidal activity and corrosion inhibition of some cationic surfactants derived from Thiol polyurethane.

Sustainable Surfactants Based on Amino Acids

Contact Info

Product

Resources

About

New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection <i>in Vitro</i>

New Amphiphilic Amino Acid Derivatives for Efficient DNA Transfection <i>in Vitro</i>