New alquil amide type cationic surfactants from arginine

Abstract

The synthesis, stability, surface activity and antimicrobial properties of a new family of cationic surfactants (the long chain arginylalkylamide dihydrochloride salts) derived from the condensation of the amino acid arginine and a long chain alkylamine are described. The surface active parameters reported are c.m.c. (critical micellar concentration), pC 20 (negative log of the surfactant molar concentration required to reduce the surface tension of the solvent by 20 mN m Ϫ1 ), c.m.c. (the surface tension at the c.m.c.), max (the maximum surface excess concentration) and A min (the minimum area per surfactant molecule at the interface). These data and those obtained from the evaluation of the antimicrobial properties are compared with the data corresponding to another family of cationic surfactants reported earlier by our group: the long chain N -acylarginine methyl ester salts.Moreover, the synthesis of analogues possessing a reactive group capable of bonding to wool or cotton fibres is described: the long chain N -dichlorotriazinylarginylalkylamide monohydrochloride salts. We expect these compounds to bond to the textile substrate by the formation of a covalent bond. Confirmation of this is, however, necessary.

Amino acid-based surfactants

“…The application of biotechnological procedures was not efficient for these compounds [30]. Series 2 was at first prepared by chemical procedures [25], however papain from Carica papaya latex was found to be a suitable catalyst for the formation of amide (series 2) and ester bonds (series 3) between Cbz-Arg-OMe and various long-chain alkyl amines and fatty alcohols [26]. In all cases, papain deposited onto polyamide was found to be the best biocatalyst configuration.…”

“…Our group has a wide experience on the synthesis by means of chemical, enzymatic or, usually, by a combination of both methodologies, of amino acid-based surfactants obtained from the condensation of natural saturated fatty acids, alcohols, amines and acyl glyceride derivatives with different amino acid head groups through ester and amide linkages [18][19][20][21][22][23][24][25][26][27][28][29][30]. Thus, saturated single-chain, double-chain, gemini and amino acid glycerolipid conjugate surfactants derived from amino acids of different ionic character have resulted to be, in all cases, highly biodegradable, with low toxicity, ecotoxicity and irritation effects.…”

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

“…Further, gemini surfactants also exhibit unique aggregation properties such as premicellar formation below the cmc [5][6][7] and vesicle formation at low concentrations in the case of long hydrocarbon chains [8,9]. Recently, en- Scheme 1. were synthesized [15][16][17] and their physicochemical properties, antimicrobial activity, and biodegradability were investigated in detail. Recently, Roy et al [18] investigated supramolecular chirality in ketone reduction by changing the headgroup geometry of four amino acid-based cationic surfactants.…”

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

“…Previously published work indicates that the preparation of arginine N-alkyl amide derivatives by the classical process results in low global reaction yield (ranging from 20 to 30%), due to the removal of byproducts formed from the coupling reagent during the purification process. 25 Also, the chemical synthesis of arginine alkyl ester derivatives requires higher temperatures and strong acid conditions, which are not always compatible with the stability of the amino acid.…”