MICELLAR ATTACK OF ARGININE-BASED SURFACTANTS TOWARDS THE ERYTHROCYTE MEMBRANE

FAIT, M.E.; HERMET, M.; COMELLES, F.; CLAPÉS. P.; ÁLVAREZ, A.; PRIETO, E.; MORCELLE, S.R.; BAKÁS, L.

Tucumán

Congreso; IIILAFeBS, IX IberoAmerican Congress of Biophysics, XLV Reunion Anual SAB 2016.; 2016

Surfactants are key compounds in pharmaceutical industry. Commercial surfactants commonly used are toxic and have a negative impact on the environment due to their low biodegradability and hazardous manufacture. Synthetic amphipatic structures that mimic natural ones, such as amino acid-based surfactants, constitute an important class of natural surface active molecules, with remarkable biological and biocompatible properties, such as low toxicity, high biodegradability and a minimal environmental impact. Among them, arginine-based surfactants in particular constitute an interesting group of amino acid-based surfactants, since they are generally non-toxic and highly biodegradable cationic compounds with excellent broad-spectrum antimicrobial properties. According to their structure, arginine-based surfactants can be classified into three categories: i) single chain surfactants, ii) dimeric (gemini) surfactants and iii) glycerolipid conjugates. Two novel arginine-based compounds belonging to the first group mentioned (Bz-Arg-NHC10 and Bz-Arg-NHC12) were synthesized in our laboratory by means of a biocatalytic strategy. Papain from Carica papaya latex was used as biocatalyst for the condensation reaction between Nα-benzoyl-arginine ethyl ester hydrochloride (BAEE) and decyl-/dodecylamine as nucleophiles. In this work we characterize the surface properties of Bz-Arg-NHCn and describe the morphology of their aggregates. Furthermore, we also study and analyze the hemolytic process induced by Bz-Arg-NHCn to give a sharper focus on the surfactant conformation (monomer or aggregate) responsible of it.