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.
N-polyfluoroalkyl derivatives of 6-deoxy-6-ethylamino-1,2;3,4-di-O-isopropylidene-alpha-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.
Kaplánek
Robert
R
Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic.
Polák
Radek
R
Paleta
Oldrich
O
Kefurt
Karel
K
Moravcová
Jitka
J
Krenová
Iva
I
Kodícek
Milan
M
D004655:Emulsions; D004912:Erythrocytes / Q000187:drug effects*; D005021:Ethylamines / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry; D005690:Galactose / Q000009:adverse effects / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008744:Methylamines / Q000737:chemistry*; D009025:Morpholines / Q000737:chemistry; D020442:Poloxamer / Q000737:chemistry; D013012:Sorbitol / Q000009:adverse effects / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D004655:Emulsions; D005021:Ethylamines; D005466:Fluorocarbons; D006845:Hydrocarbons, Fluorinated; D008744:Methylamines; D009025:Morpholines; D020442:Poloxamer; D013012:Sorbitol; C008805:perfluorodecalin; D005690:Galactose