Adsorption and aggregation properties of amino acid-based N-alkyl cysteine monomeric and -dialkyl cystine gemini surfactants

Yoshimura, Tomokazu; Sakato, Ayako; Tsuchiya, Koji; Ohkubo, Takahiro; Sakai, Hideki; Abe, Masahiko; Esumi, Kunio

doi:10.1016/j.jcis.2006.11.038

Cited by 84 publications

(67 citation statements)

References 41 publications

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“…In the case of the monovalent cationic surfactants n was taken as 2 since the surface tension was measured in neat water [46] while it was taken as 1 for the two anionic surfactants due to the presence of NaOH 0.0100 mol dm −3 in solution [47]. Table 1 lists the interfacial parameters determined for the studied surfactants.…”

Section: Micellization Propertiesmentioning

confidence: 99%

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Brito

Marques

Silva

et al. 2009

Colloids and Surfaces B: Biointerfaces

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a b s t r a c tThe design of efficient liposomal systems for drug delivery is of considerable biomedical interest. In this context, vesicles prepared from cationic/anionic surfactants may offer several advantages, mainly due to their spontaneity in formation and long-term stability. There is also an impending need to produce less toxic, more biocompatible amphiphiles, while maintaining the desirable aggregation properties. In this work, we present data for acute toxicity to Daphnia magna (IC 50 ), and potential ocular irritation (HC 50 ) for some newly prepared ionic surfactants with dodecyl chains, derived from the amino acids tyrosine (Tyr), serine (Ser), hydroxyproline (Hyp) and lysine (Lys). The micellization behavior of the compounds, evaluated from surface tension measurements, is presented and compared to more conventional ionic amphiphiles. Two types of spontaneouly formed catanionic vesicles, composed either by a dodecyltrimethylammonium bromide (DTAB)/Lys-derivative and or Ser-/Lys-derivative mixture, have also been tested for their ecotoxicity and hemolytic potential. All the micelle-forming surfactants as well as the vesicle-containing mixtures are found to have lower ecotoxicity than the reference surfactant DTAB. Moreover, the results from hemolysis and hemoglobin denaturation tests show that the Tyr-and Lys-derivatives are moderately irritant, whereas the Hyp-and Ser-ones are just slightly irritant. Even more significantly, the vesicle-containing mixtures exhibit lower hemolytic activity than the neat surfactants, a positive result for their potential use in liposomal formulations.

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Section: Micellization Propertiesmentioning

confidence: 99%

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Brito

Marques

Silva

et al. 2009

Colloids and Surfaces B: Biointerfaces

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“…We attempted cryogenic transmission electron microscopy cryo-TEM observation for the micelles of 2C n diCys; however, a clear image was not observed because of the formation of small micelles. The aggregation behavior of 2C n diCys differed from that of the 2C n Cys cystine-based gemini surfactants, which have been reported previously 15 . For n 12, DLS, cryo-TEM, and SANS measurements showed that 2C 12 Cys simultaneously formed 2 aggregates of small rod-like micelles that were 15 nm in length and small unilamellar vesicles with a diameter of 20 nm at a concentration of 0.832 mmol dm 3 in solution.…”

Section: Micelle Formation In Solutionmentioning

confidence: 41%

“…N-Alkyl cysteine was synthesized in methanol containing NaOH by reacting cysteine and n-alkyl bromide alkyl decyl, dodecyl, or tetradecyl according to previously described methods 15 . Adipoyl chloride was added to a stirred solution of N-alkyl cysteine 2.2-fold molar excess for adipoyl chloride in tetrahydrofuran at 5 ; this mixture was stirred for 24 h. After the solvent was removed by evaporation, the residue obtained was dissolved in acetone and the solution was filtered to remove nonsoluble material.…”

Section: Synthesis Of Cysteine-based Gemini Surfactantmentioning

confidence: 99%

Solution Properties and Emulsification Properties of Amino Acid-Based Gemini Surfactants Derived from Cysteine

2013

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“…Surfactants derived from sulfur-based amino acids such as cysteine have been found to show very interesting and unique physicochemical properties [9][10][11]. N-alkylamine surfactants derived from cystine and cysteine have been reported to form micelles and small lamellar vesicles in aqueous solutions [12]. Amide surfactants derived from cystine have been reported to show interesting surface properties and aggregation behaviour which allowed them to form various structures such as spherical vesicles [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and physicochemical properties of non-ionic and cationic surfactants derived from methionine

Joondan

Radhan

Laulloo

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Amino acid based surfactants have been widely used as alternative to classical surfactants due to their interesting physicochemical properties, biological activities, biodegradability and low toxicity. The study of the physicochemical properties of surfactants such as critical micelle concentration (CMC) and Krafft temperature is an important aspect in determining their use in detergents or pharmaceutical compositions. In this study, a series of non-ionic and cationic surfactants with varying chain lengths (C8-C12), namely the O-alkyl esters of methionine and their hydrochloride derivatives respectively were synthesized and characterized by spectral data.In view of systematically studying the effect of the head group and chain length on the physicochemical properties, the critical micelle concentrations of both series were evaluated using conductivity measurements and pyrene fluorescence spectroscopy. The Krafft temperatures of selected synthesized methionine-based surfactants were also evaluated. The methionine surfactants were synthesized in good to moderate yield (54 -81%). For both ester and the hydrochloride series, the CMC of the surfactants were found to decrease with chain length, as commonly observed for all surfactants. The non-ionic O-alkyl esters of methionine displayed relatively lower CMC values compared to their ester hydrochloride derivatives for all the chain length studied. The ester hydrochloride derivatives showed an increase in the Krafft temperature with increasing chain length showing that the surfactants with longer chain length has a tendency to micellise at a much higher temperature.

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Adsorption and aggregation properties of amino acid-based N-alkyl cysteine monomeric and -dialkyl cystine gemini surfactants

Cited by 84 publications

References 41 publications

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Solution Properties and Emulsification Properties of Amino Acid-Based Gemini Surfactants Derived from Cysteine

Synthesis and physicochemical properties of non-ionic and cationic surfactants derived from methionine

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