Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants

M. Elisa Fait, Graciela L. Garrote, Pere Clapés, Sebastian Tanco, Julia Lorenzo, Susana R. Morcelle

Research output: Contribution to journalArticleResearchpeer-review

12 Citations (Scopus)

Abstract

© 2015 Springer-Verlag Wien. 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.
Original languageEnglish
Article number1979
Pages (from-to)1465-1477
JournalAmino Acids
Volume47
Issue number7
DOIs
Publication statusPublished - 9 Jul 2015

Keywords

  • Antimicrobial activity
  • Arginine-based surfactants
  • Biocatalysis
  • Cytotoxic effect
  • Papain

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