Nonionic amphiphilic compounds from lysine as molecular mimics of lecithins

Abstract

New monodisperse nonionic surfactant molecules, based on lysine with two fatty acid chains in the hydrophobic part and one or two polyoxyethylene methoxycapped chains (EOn−Me) in the hydrophilic headgroup, are synthesized as mimics of natural lecithins. Their surface‐activity properties indicate that these compounds have surfactant behavior whose global hydrophobic contribution is comparable to that of one fatty chain.

Alkyl glucopyranoside-based niosomes containing methotrexate for pharmaceutical applications: Evaluation of physico-chemical and biological properties

“…At high surfactant concentrations the cell membranes disrupt and the surfactant solubilizes the membrane lipids. The hemolytic power of the surfactant is influenced not only by their hydrophilic and hydrophobic character, but also by the aggregate properties, which affect the surfactant intercalation into the erythrocyte membrane (Isomaa et al, 1986;Zaslawsky et al, 1978;Seguer et al, 1994). These hypotheses explain the results achieved in niosomal formulations: small niosomes (A formulation) are more toxic than large ones (C formulation), because they easily interact with erythrocytes, causing substantial hemolysis.…”

Amino acid-based surfactants

“…Our group has a wide experience on the synthesis by means of chemical, enzymatic or, usually, by a combination of both methodologies, of amino acid-based surfactants obtained from the condensation of natural saturated fatty acids, alcohols, amines and acyl glyceride derivatives with different amino acid head groups through ester and amide linkages [18][19][20][21][22][23][24][25][26][27][28][29][30]. Thus, saturated single-chain, double-chain, gemini and amino acid glycerolipid conjugate surfactants derived from amino acids of different ionic character have resulted to be, in all cases, highly biodegradable, with low toxicity, ecotoxicity and irritation effects.…”

Amino Acids, Lactic Acid and Ascorbic Acid as Raw Materials for Biocompatible Surfactants

“…Symmetrical (two equal fatty acid chains) ( Figure 5.4, 1) and asymmetrical (two different fatty acid chains) ( Figure 5.4, 2) nonionic double-chain surfactants of the type N α ,N ε -diacyl lysine polyoxyethylene glycol amide compounds, with a structural resemblance to natural lecithin phospholipids, have been reported by the authors' lab [35][36][37][38] to determine the effect of several structural parameters (hydrophobic chain length, polyoxyethylene (POE) chain length and number of polyoxyethylene chains) on the physicochemical properties and biological performance of these natural mimics.…”

“…Seguer et al [36,37] studied the micellization properties of the same basic structure, N α ,N ε -diacyl lysine oxyethylene derivatives linked to the acid group via an amide bond ( Figure 5.4, 1). The EO chains increase the water solubility of the products and allow for CMC determination.…”

“…The area per molecule as obtained from surface tension measurements gives a high value for the dioctyl lysine derivatives [49,51], agreeing with the small micellar sizes. Longer derivatives [36,37]; squares: N α ,N ε -diacyl lysine dimethyl ether dipolyoxyethylene glycol amides [36,37]; triangles N α ,N ε -diacyl lysine salts with several counterions [37,49,50,53], compared to short-chain lecithins (crosses) (dihexanoyl lecithin and dioctanoyl lecithin) [37].…”