Perfluoroalkylated derivatives of 6-deoxy-6-ethylamino-d-galactose, 1-deoxy-1-methylamino-d-glucitol, and 1-amino-1-deoxy-d-glucitol: syntheses, hemocompatibility, and effect on perfluorocarbon emulsion |
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Authors: | Robert Kaplánek Old?ich Paleta Karel Kefurt Iva K?enová |
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Institution: | a Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic b Department of Natural Compounds Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic c Department of Biochemistry and Microbiology, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic |
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Abstract: | N-Polyfluoroalkyl derivatives of 6-deoxy-6-ethylamino-1,2;3,4-di-O-isopropylidene-α-d-galactopyranose (8-10), 1-deoxy-1-methylamino-d-glucitol (13-15), and 1-amino-1-deoxy-d-glucitol (16-18), all possessing perfluoroalkyl segment, were prepared using nucleophilic epoxide ring opening of 2-(perfluoroalkyl)methyl]oxiranes 1-3. Co-emulsifying properties and hemolytic activity of the new perfluoroalkylated amphiphiles were tested. Both types of the polyol derivatives 8-10 and 13-18 generally displayed good to excellent co-emulsifying properties on testing on perfluorodecalin/Pluronic F-68 microemulsions. Mono-perfluoroalkylated compounds 8-10 and 13-15 displayed high hemolysis, whereas acyclic bis-perfluoroalkylated compounds 16-18 were non-hemolytic even for short perfluorobutyl segment (16). The properties were generally improving with increasing perfluoroalkyl chain length. |
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Keywords: | 2-[(Perfluoroalkyl)methyl]oxiranes N-Polyfluoroalkylation Fluoroalkyl surfactants Polyfluoroalkylated aminosaccharides Hemocompatibility Microemulsion stability |
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