The present invention concerns the preparation of cationic surfactants derived from the condensation of an acid chloride, preferably a fatty acid with a number of carbon atoms 8, 9 and 14 with esterified amino acids, preferably basic-type amino acids, like (L)-arginine. The method comprises a first step in which the esterification of the amino acid with an alcohol is performed and a second step for the condensation with a chloride of fatty acid, using Schotten Baumann conditions. These surfactants constitute a novel class of chemicals of low toxicity with excellent surface properties and considerable antimicrobial activity. As in a conventional series of surfactants with different chain lengths, changes in the chain result in changes in the physicochemical properties. Excellent antimicrobial activity is observed for the homologue of 14 carbon atoms.
A mino acid-based surfactants constitute a class of cationic surfactants with excellent surface p roperties, wide biological activ ity, low potential to xicity. Essential structural factors for their antimicrobial activity include both the length of the fatty residue and the presence of the protonated guanidine function. These features and the use of natural raw materials such as Arginine and fatty acids for their synthesis, make them interesting candidates as preservatives and antiseptics in pharmaceutical, food and cosmetic fo rmulat ions. The present work describes the synthesis (at lab scale), the physicochemical properties of long chain N α -acyl arginine ethyl esters with a chain of 8 and 9 carbon atoms. These compounds have been prepared by condensation of L-arg inine ethyl ester dihydrochloride with corresponding acyl chlorides in the presence of base. The basic charastristic properties such as physical appearance, structural identificat ion by IR/ H 1 NMR, water solubility at different pH and surface tension studies of the synthesized co mpounds are discussed. The Antimicrobial properties of the co mpounds of invention are studied by determin ing their M inimu m inhibitory concentration for different microorganisms.
Amino-acid derived compounds, for example N-α-lauroylarginine ethyl ester (LAE), N-α-myristoylarginine ethyl ester (MAE) and a 1:1 mixture of N-α-myristoylarginine ethyl ester with monolaurin (MAE + MLN) are examined for their cytotoxicity towards L929-Mouse connective tissue to explore their use as microbicidal agent, in comparison to sodium dodecylsulfate (SDS) as an anionic control detergent. MTT (4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Cytotoxicity assay method was used to determine IC50 value. Cytotoxicity of MAE is found to be more toxic as compared to LAE, having IC50 value 0.052 mg/ml against 0.68 mg/ml of LAE. But MAE when mixed with monolaurin (1:1), showed less toxicity with IC50 0.89 mg/ml. These results suggest that a combination of MAE and Monolaurin can be a potential candidate for studying its microbicidal properties.
Amino-acid derived compounds, for example N-α-lauroylarginine ethyl ester (LAE), N-α-myristoylarginine ethyl ester (MAE) and a 1:1 mixture of N-α-myristoylarginine ethyl ester with monolaurin (MAE + MLN) are examined for their cytotoxicity towards L929-Mouse connective tissue to explore their use as microbicidal agent, in comparison to sodium dodecylsulfate (SDS) as an anionic control detergent. MTT (4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cytotoxicity assay method was used to determine IC50 value. Cytotoxicity of MAE is found to be more toxic as compared to LAE, having IC50 value 0.052 mg/ml against 0.68 mg/ml of LAE. But MAE when mixed with monolaurin (1:1), showed less toxicity with IC50 0.89 mg/ml. These results suggest that a combination of MAE and Monolaurin can be a potential candidate for studying its microbicidal properties.
The invention concerns the preparation of cationic surfactants derived from the condensation of an acid chloride, preferably a fatty acid with a number of carbon atoms 8 and 14 with esterified amino acids, preferably basic-type amino acids, like (L)-Lysine and (L)-arginine, more preferably (L)-arginine. The method comprises a first step in which the esterification of the amino acid with an alcohol is performed and a second step for the condensation with a chloride of fatty acid, using Schotten Baumann conditions. These surfactants constitute a novel class of chemicals of low toxicity with excellent surface properties and considerable antimicrobial activity. The physicochemical properties of the compounds of invention are compared against commercially available LAE (Lauroylarginine Et ester) and SDS (sodium dodecyl sulfate).
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