- Interaction of arginine-based cationic surfactants with lipid membranes. An experimental and molecular simulation study
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The effect of two arginine-based cationic surfactants, arginine N-lauroyl amide dihydrochloride and arginine O-lauroyl ester dihydrochloride, upon dipalmitoylphosphatidylcholine liposomes, is addressed in this work. Some aspects concerning the synthesis of these surfactants are also presented in some detail. Differential scanning calorimetry, as well as fluorescence anisotropy using several probes, is used to assess the relative effects on the lipid model membranes. In spite of the structural similarity among these molecules, which differ only by the group that connects the polar head to the tail, experimental results suggest differences in their behavior. Molecular dynamics simulation provides significant insight into the molecular mechanism that governs this interaction. A rationale is provided in terms of lipid-surfactant hydrogen bonding and the consequent positioning of the surfactant molecule within the bilayer.
- Almeidaa, Joao A. S.,Morana, Maria C.,Infanteb, Maria R.,Paisa, Alberto A. C. C.
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scheme or table
p. 34 - 50
(2010/08/22)
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- Synthesis and biological properties of dicationic arginine-diglycerides
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A novel family of dicationic arginine-diglyceride surfactants, 1,2-diacyl-3-O-(L-arginyl)-rac-glycerol·2HCl (XXR) with alkyl chain lengths in the range of C8-C14 was prepared. These new surfactants can be regarded as analogues of lecithins. They have two hydrophobic tails of identical fatty acid chains attached to the glycerol through ester bonds and a dicationic polar head from arginine instead of the zwitterionic on the lecithins. These new compounds can be classified as multifunctional surfactants with self-aggregation behaviour comparable to that of short-chain lecithins. They have antimicrobial activity similar to that of the conventional cationic surfactants and are as harmless as amphoteric betaines.
- Perez,Pinazo,Vinardell,Clapes,Angelet,Infante
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p. 1221 - 1227
(2007/10/03)
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