New perfluoroalkyl telomeric non‐ionic surfactants: synthesis, physicochemical and biological properties

Abstract

Both the experimental conditions and the kinetic parameters governing the telomerization of hydroxy-functional acryloyl derivatives in the presence of perfluoroalkanethiols were determined with the purpose of synthesizing new amphiphilic telomers with high surface activity for the preparation of stable perfluoro emulsions capable of carrying oxygen in vivo. Several perfluoroalkylated non-ionic telomeric surfactants (FniTACn) were obtained in one step with an average yield of 8O%, by free-radical telomerization of tris(hydroxymethy1)acrylamidomethane in the presence of various perfluoroalkanethiols as chain-transfer reagents. Surface activity, critical micelle concentration and emulsifying capability established the superiority of the FniTACn surfactants over Pluronic@ F68, the major surfactant used presently in the FDA-approved injectable fluorocarbon emulsion: FluosoP. *) Systematic names: N-[tris(hydroxymethyl)methyl]acrylamide (THAM) or -methacrylamide (MTHAM).

Polysoaps with fluorocarbon hydrophobic chains

“…In particular, the use of fluorocarbon hydrophobic chains in polymers has so far been very limited. The few studies have been restricted basically to water-soluble polymers which are weakly substituted with fluorocarbon chains to provide efficient thickeners [5][6][7][8][9][10], or to block copolymers [11][12][13][14][15] or oligomers [16,17] respectively. Examples for water-soluble polymers which are heavily substituted with fluorocarbon chains, as needed for polysoaps to enable intramolecular aggregation, are virtually missing.…”

Inhibition of angiogenesis by THAM-derived cotelomers endowed with thalidomide moieties

“…29 Telomerization experiments (Fig. 3) were carried out by refluxing compounds 4 and 5 in methanol under a nitrogen atmosphere in the presence of octanethiol as transfer reagent and AIBN as radical initiator.…”

Novel Asparagine-Derived Lipid Enhances Distearoylphosphatidylcholine Bilayer Resistance to Acidic Conditions

“…30–32 Recently, Sorrells and Menger 33 reported that a serine-derived diketopiperazine lipid influenced the formation and stabilization of micellar aggregates. Asparagine-derived lipids have been reported 34 in liposomes for nucleic acid delivery with effective controlled release properties, 34a for the preparation of long-circulating liposomes with drug-targeting capacities, 34b and to trigger vesicle fusion.…”