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Perfluoroalkylated fatty acid monoesters of trehalose and sucrose for biomedical applications: Remarkable emulsifying properties of 6‐ O ‐[3′‐(perfluorooctyl) propanoyl]‐trehalose
Author(s) -
Abouhilale Samir,
Greiner Jacques,
Riess Jean G.
Publication year - 1992
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02635867
Subject(s) - trehalose , pulmonary surfactant , surface tension , chemistry , emulsion , sucrose , amphiphile , poloxamer , fatty acid , chromatography , organic chemistry , biochemistry , copolymer , physics , quantum mechanics , polymer
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 C 8 F 17 CH 2 CH 2 C(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 LD 50 was found to be in the range of 250–375 mg/kg of body weight i.v. in mice.