Cationic surfactants from lysine: Synthesis, micellization and biological evaluation

Membrane-destabilizing activity of pH-responsive cationic lysine-based surfactants: role of charge position and alkyl chain length

“…Several studies have been performed to demonstrate a correlation between hemolytic activity and the CMC of surfactants; however, there are no clear conclusions in the literature (Pérez et al 2009;Preté et al 2002;Spengler et al 2011). …”

“…The commercial cationic surfactant hexadecyl trimethyl ammonium bromide ( HTAB) was used as the reference compound. These lysine-based surfactants were synthesized in our laboratory as previously described (Colomer et al 2011a;Pérez et al 2009) and made from natural fatty acid and amino acid organic building blocks. The chemical structure of these compounds was checked by nuclear magnetic resonance and their purity, higher than 99%, was confirmed by elemental analysis and high-performance liquid chromatography.…”

“…Furthermore, surfactants with pHresponsive membrane-disruptive activity may further destabilize endosomal compartments (Nogueira et al 2011;Wang et al 2007). The physicochemical and biological properties of cationic amino acid-based surfactants, as well as their synthesis, have been widely reported by our group (Colomer et al 2011a;Lozano et al 2011;Infante et al 2010;Pérez et al 2002Pérez et al , 2009). Therefore, we selected biocompatible cationic surfactants from the amino acid lysine (hydrochloride salts of N ε -and N α -acyl lysine methyl ester) since they display lower toxicity potential and are classified as biodegradable (Pérez et al 2009), and thus suitable for practical applications.…”

“…Those derived from amino acids usually present biocompatible properties and low cytotoxicity, and are therefore of great interest for pharmaceutical applications, especially in the field of novel non-viral drug delivery devices Pérez et al 2009). As surface properties (hydrophobicity and surface charge) have a major impact on cellular uptake of particulate drug delivery systems, the incorporation of charged surfactants into these carriers might improve targeting to specific cells (Schöler et al 2001).…”

Phospholipid Bilayer-Perturbing Properties Underlying Lysis Induced by pH-Sensitive Cationic Lysine-Based Surfactants in Biomembranes

“…[2][3][4][5][6] Surfactants derived from amino acids constitute an important class of natural surface-active biomolecules that usually have biocompatible properties and multifunctional capabilities, which make them extremely relevant for pharmaceutical applications, especially in the field of novel non-viral drug delivery devices. 4,7,8 Our group has considerable experience in the synthesis of surfactants derived from amino acids. Indeed, we recently developed new families of lysine-based surfactants, 8,9 and some of them were deeply studied here in order to find out some important characteristics of surfactant-membrane interaction.…”