Cationic surfactants from lysine: synthesis, micellization and biological evaluation.
Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of N(epsilon)-lauroyl lysine methyl ester, N(epsilon)-myristoyl lysine methyl ester and N(epsilon)-palmitoyl lysine methyl ester) have been prepared in high yields by lysine acylation in epsilon 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(alpha)-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.
Pérez
Lourdes
L
Departamento de Tecnología de Tensioactivos, Instituto de Química Avanzada de Cataluña, CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
Pinazo
Aurora
A
Teresa García
M
M
Lozano
Marina
M
Manresa
Angeles
A
Angelet
Marta
M
Pilar Vinardell
M
M
Mitjans
Montse
M
Pons
Ramon
R
Rosa Infante
M
M
D000215:Acylation; D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000633:toxicity; D001672:Biocompatible Materials / Q000138:chemical synthesis; D002412:Cations; D003621:Daphnia / Q000187:drug effects; D005227:Fatty Acids / Q000737:chemistry; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008239:Lysine / Q000737:chemistry*; D008823:Micelles; D008826:Microbial Sensitivity Tests; D013501:Surface-Active Agents / Q000138:chemical synthesis*; D018675:Toxicity Tests
D000890:Anti-Infective Agents; D001672:Biocompatible Materials; D002412:Cations; D005227:Fatty Acids; D008823:Micelles; D013501:Surface-Active Agents; D008239:Lysine