Cationic surfactants from lysine: Synthesis, micellization and biological evaluation

• Published in: European journal of medicinal chemistry Vol. 44; no. 5; pp. 1884 - 1892
• Main Authors: Pérez, Lourdes, Pinazo, Aurora, Teresa García, M., Lozano, Marina, Manresa, Angeles, Angelet, Marta, Pilar Vinardell, M., Mitjans, Montse, Pons, Ramon, Rosa Infante, M.
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.05.2009; Elsevier
• Subjects: Acylation; Animals; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - toxicity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antimicrobial properties; Biocompatible Materials - chemical synthesis; Biological and medical sciences; Cations; Chemistry, Medicinal; Daphnia - drug effects; Fatty Acids - chemistry; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Haemolysis; Life Sciences & Biomedicine; Lysine; Lysine - chemistry; Medical sciences; Micelles; Microbial Sensitivity Tests; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Surface-Active Agents - chemical synthesis; Surfactants; Toxicity Tests; Haemolysis; Antimicrobial properties; Surfactants; Lysine; EPSILON-ACYLLYSINE DERIVATIVES; QUATERNARY AMMONIUM-COMPOUNDS; HEMOLYSIS; PEPTIDE; NONIONIC AMPHIPHILIC COMPOUNDS; ANTIMICROBIAL ACTIVITIES; AMINO-ACIDS; ARGININE; DIFFUSION; GEMINI SURFACTANTS; Biodegradability; Toxicity; Cladocera; Cationic surfactant; Cytotoxicity; Antimicrobial agent; Crustacea; Aminoester; Gram positive bacteria; Chemical synthesis; Branchiopoda; Hemolysis; Red blood cell; In vitro; Biological activity; α-Aminoacid; Arthropoda; Invertebrata; Antibacterial agent; Daphnia magna; Micellization
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2008.11.003

Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of N ɛ-lauroyl lysine methyl ester, N ɛ-myristoyl lysine methyl ester and N ɛ-palmitoyl lysine methyl ester) have been prepared in high yields by lysine acylation in ɛ position with three natural saturated fatty acids. The micellization process of these surfactants has been studied using the PGSE-NMR technique. The compounds were tested as antimicrobial agents against Gram-positive and Gram-negative bacteria. The surfactants show moderate antimicrobial activity against the Gram-positive bacteria but Gram-negative bacteria are resistant to these surfactants in the concentration range tested. The haemolytic activity is considerably lower than those reported for other cationic N α-acyl amino acid analogues. The acute toxicity against Daphnia magna and biodegradability was studied. The toxicity is clearly lower than that reported for conventional cationic surfactants from quaternary ammonium and the three surfactants from lysine can be classified as ready biodegradable surfactants. Cationic N ɛ-acyl lysine methyl ester surfactants were prepared using classical synthetic methods. We were evaluated for such physicochemical properties as critical micellar concentration and also such biological properties as antimicrobial activity, ecotoxicity, biodegradation and haemolytic activity. [Display omitted]