title: Cationic surfactants derived from lysine: effects of their structure and charge type on antimicrobial and hemolytic activities.
abstract: Three different sets of cationic surfactants from lysine have been synthesized. The first group consists of three monocatenary surfactants with one lysine as the cationic polar head with one cationic charge. The second consists of three monocatenary surfactants with two amino acids as cationic polar head with two positive charges. Finally, four gemini surfactants were synthesized in which the spacer chain and the number and type of cationic charges have been regulated. The micellization process, antimicrobial activity, and hemolytic activity were evaluated. The critical micelle concentration was dependent only on the hydrophobic character of the molecules. Nevertheless, the antimicrobial and hemolytic activities were related to the structure of the compounds as well as the type of cationic charges. The most active surfactants against the bacteria were those with a cationic charge on the trimethylated amino group, whereas all of these surfactants showed low hemolytic character.
authors.affiliation: Departamento de Tecnología Química y de Tensioactivos, IQAC, CSIC, C/Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: A
authors.initials: A
authors.lastname: Colomer
authors.forename: A
authors.initials: A
authors.lastname: Pinazo
authors.forename: M A
authors.initials: MA
authors.lastname: Manresa
authors.forename: M P
authors.initials: MP
authors.lastname: Vinardell
authors.forename: M
authors.initials: M
authors.lastname: Mitjans
authors.forename: M R
authors.initials: MR
authors.lastname: Infante
authors.forename: L
authors.initials: L
authors.lastname: Pérez
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004553:Electric Conductivity; D004912:Erythrocytes / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D008826:Microbial Sensitivity Tests; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013499:Surface Properties; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D008823:Micelles; D013501:Surface-Active Agents; D008239:Lysine