Chemical structure/property relationship in single-chain arginine surfactants

In this paper, a systematic investigation into the structure-property relat ionship of long-chain N-alkyl amide 1, O-alkyl ester arginine 2, and N-acyl arginine methyl ester analogues 3 is reported. The surface properties were studied by adsorption isotherm curves. Biological properties such as antim icrobial activity, hemolysis, ocular irritation, aquatic toxicity, and biod egradability are discussed and correlated with some specific parameters of the surfactants. These surfactants constitute a novel class of bio-based ma terials of low toxicity, excellent surface properties, and a wide antimicro bial activity. They selectively disrupt bacteria membranes at submicellar c oncentrations, but not erythrocytes or skin cell membranes. The presence of two positive cationic charges enhances the antimicrobial activity. The inc orporation of ester functionality accelerates biodegradation, From the data obtained, it was concluded that the hydrophobicity is a negative parameter for the toxicity and biodegradability of these surfactants.