Lysine-bisglycidol conjugates as novel lysine cationic surfactants.
The synthesis of a novel class of lysine-based cationic amphiphilic derivatives of the type N(epsilon),N(epsilon)'-bis(n-acyloxypropyl)-l-lysine methyl ester salts combining several hydroxyl functions and aliphatic chains of 12 or 14 carbon atoms is described. The compounds have one, two, three, and four alkyl chains. Aggregation in water was studied by four different methods: surface tension, conductivity, chloride ion activity, and nuclear magnetic resonance ((1)H NMR). The critical aggregation concentration value of the new surfactants depends on both the number of alkyl chains and the alkyl chain length. The formation of vesicles at low concentrations was confirmed by H(1) NMR and optical microscopy. Antimicrobial activity was determined on the basis of the minimum inhibitory concentration (MIC) values. These novel lysine-based surfactants showed moderate antimicrobial activity which may be an important advantage for many biomedical applications.
Pinazo
Aurora
A
Departament de Tecnologia Quimica i de Tensioactius, Institut de Quimica Avancada de Catalunya, CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
Angelet
Marta
M
Pons
Ramon
R
Lozano
Marina
M
Infante
Ma Rosa
MR
Pérez
Lourdes
L
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D008239:Lysine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013501:Surface-Active Agents / Q000737:chemistry* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D013501:Surface-Active Agents; D008239:Lysine