Perfluoroalkylated fatty acid monoesters of trehalose and sucrose for biomedical applications: Remarkable emulsifying properties of 6-O-[3′-(perfluorooctyl) propanoyl]-trehalose

A new series of perfluoroalkylated fatty acid monoesters of α,α-trehalose and sucrose has been evaluated with respect to their physicochemical and biological properties for possible biomedical use. These water-soluble compounds strongly reduce the water surface tension and fluorocarbon/water interfacial tension. As co-surfactants in perfluorodecalin/Pluronic F-68 type emulsions they significantly increase the stability of these emulsions. Remarkably stable concentrated perfluorodecalin-in-water (50% w/v) emulsions were obtained when the C₈F₁₇CH₂CH₂C(O)-α,α-trehalose monoester was used as the sole surfactant, while no emulsion could be obtained with its maltoside analogue. No significant effect on the growth and viability of Namalva cell cultures and no hemolytic activity on human erythrocytes at concentrations up to 50 g/L were detected for these amphiphiles in spite of their high surface activity. The LD₅₀ was found to be in the range of 250–375 mg/kg of body weighti.v. in mice.