Novel Fluorinated Surfactants for Perfluorochemical Emulsification: Biocompatibility Assessments of Glycosidic and Polyol Derivatives

Abstract

A novel series of fluoro-surfactants, derived from glycosides (monosaccharides) or polyols (ureas or carbamates), have been produced for use in respiratory gas-carrying perfluorochemical emulsions. Compounds were synthesised via simple, but highly selective, routes using highly fluorinated isocyanates with amino alcohols, polyethoxylated alcohols and partially protected sugars at anomeric carbon; yields were 88–95%. Resultant compounds were perfluoroalkylated with hydroxylic “head” groups. The biocompatibility of surfactants with human blood in vitro was assessed using a conventional haemolysis test. Compounds showing insignificant haemolysis at up to 10 g l⁻¹ were further evaluated (i) for their effects on neutrophil chemiluminescence, and (ii) in a human platelet aggregation assay. Some fluoro-surfactants inhibited spontaneous platelet aggregation, in blood anti-coagulated with hirudin, at concentrations of 0.01% (w/v), suggesting possible applications as antithrombotic agents.