title: Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants.
abstract: Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N (α)-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N (α)-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N (α)-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.
authors.affiliation: Centro de Investigación de Proteínas Vegetales (CIPROVE), Departamento de Ciencias Biológicas, Facultad de Ciencias Exactas, Universidad Nacional de La Plata (UNLP), La Plata, Argentina.
authors.forename: M Elisa
authors.initials: ME
authors.lastname: Fait
authors.forename: Graciela L
authors.initials: GL
authors.lastname: Garrote
authors.forename: Pere
authors.initials: P
authors.lastname: Clapés
authors.forename: Sebastian
authors.initials: S
authors.lastname: Tanco
authors.forename: Julia
authors.initials: J
authors.lastname: Lorenzo
authors.forename: Susana R
authors.initials: SR
authors.lastname: Morcelle
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D055162:Biocatalysis; D002470:Cell Survival / Q000187:drug effects; D002852:Chromatography, Ion Exchange; D004912:Erythrocytes / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006461:Hemolysis; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D010206:Papain / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D013501:Surface-Active Agents; D001120:Arginine; D010206:Papain