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Cationic surfactants from lysine: Synthesis, micellization and biological evaluation

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Title: Cationic surfactants from lysine: Synthesis, micellization and biological evaluation
Authors: Pérez, Lourdes1 lpmste@cid.csic.es, Pinazo, Aurora1, Teresa García, M.1, Lozano, Marina1, Manresa, Angeles2, Angelet, Marta1, Pilar Vinardell, M.3, Mitjans, Montse3, Pons, Ramon1, Rosa Infante, M.1
Source: European Journal of Medicinal Chemistry. May2009, Vol. 44 Issue 5, p1884-1892. 9p.
Subject Terms: *Surface active agents, Organic synthesis, Biomedical materials, Lysine, Acylation, Pharmaceutical chemistry, Anti-infective agents
Abstract: Abstract: Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of Nɛ-lauroyl lysine methyl ester, Nɛ-myristoyl lysine methyl ester and Nɛ-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 Nα-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. [Copyright &y& Elsevier]
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Abstract:Abstract: Biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of Nɛ-lauroyl lysine methyl ester, Nɛ-myristoyl lysine methyl ester and Nɛ-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 Nα-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. [Copyright &y& Elsevier]
ISSN:02235234
DOI:10.1016/j.ejmech.2008.11.003