title: New cationic vesicles prepared with double chain surfactants from arginine: Role of the hydrophobic group on the antimicrobial activity and cytotoxicity.
abstract: Cationic double chain surfactants have attracted much interest because they can give rise to cationic vesicles that can be used in biomedical applications. Using a simple and economical synthetic approach, we have synthesized four double-chain surfactants with different alkyl chain lengths (LANHCx). The critical aggregation concentration of the double chain surfactants is at least one order of magnitude lower than the CMC of their corresponding single-chain LAM and the solutions prepared with the LANHCx contain stable cationic vesicles. Encouragingly, these new arginine derivatives show very low haemolytic activity and weaker cytotoxic effects than conventional dialkyl dimethyl ammonium surfactants. In addition, the surfactant with the shortest alkyl chain exhibits good antimicrobial activity against Gram-positive bacteria. The results show that a rational design applied to cationic double chain surfactants might serve as a promising strategy for the development of safe cationic vesicular systems.
authors.affiliation: Department of Chemical and Surfactant Technology, IQAC, CSIC, C/JordiGirona 18-26, 08034 Barcelona, Spain.
authors.forename: A
authors.initials: A
authors.lastname: Pinazo
authors.affiliation: Department of Chemical and Surfactant Technology, IQAC, CSIC, C/JordiGirona 18-26, 08034 Barcelona, Spain.
authors.forename: V
authors.initials: V
authors.lastname: Petrizelli
authors.affiliation: Department of Chemical and Surfactant Technology, IQAC, CSIC, C/JordiGirona 18-26, 08034 Barcelona, Spain.
authors.forename: M
authors.initials: M
authors.lastname: Bustelo
authors.affiliation: Department of Chemical and Surfactant Technology, IQAC, CSIC, C/JordiGirona 18-26, 08034 Barcelona, Spain.
authors.forename: R
authors.initials: R
authors.lastname: Pons
authors.affiliation: Departament of Physiology, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XIII s/n, 08028 Barcelona, Spain.
authors.forename: M P
authors.initials: MP
authors.lastname: Vinardell
authors.affiliation: Departament of Physiology, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XIII s/n, 08028 Barcelona, Spain.
authors.forename: M
authors.initials: M
authors.lastname: Mitjans
authors.affiliation: Departament of Microbiology, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XIII s/n, 08028 Barcelona, Spain.
authors.forename: A
authors.initials: A
authors.lastname: Manresa
authors.affiliation: Department of Chemical and Surfactant Technology, IQAC, CSIC, C/JordiGirona 18-26, 08034 Barcelona, Spain. Electronic address: lourdes.perez@cid.csic.es.
authors.forename: L
authors.initials: L
authors.lastname: Perez
mesh_terms: D016475:3T3 Cells; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology; D001120:Arginine / Q000737:chemistry*; D002412:Cations / Q000737:chemistry*; D002461:Cell Line, Transformed; D002470:Cell Survival / Q000187:drug effects; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D020128:Inhibitory Concentration 50; D051379:Mice; D008823:Micelles; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D015394:Molecular Structure; D013500:Surface Tension; D013501:Surface-Active Agents / Q000737:chemistry* / Q000494:pharmacology; D013696:Temperature
chemical_list: D000890:Anti-Infective Agents; D002412:Cations; D008823:Micelles; D013501:Surface-Active Agents; D001120:Arginine
keywords: Antimicrobial activity; Arginine-based surfactants; Cationic vesicles; Cytotoxicity