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
Language English Country Netherlands Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
20382375
DOI
10.1016/j.carres.2010.03.023
PII: S0008-6215(10)00119-9
Knihovny.cz E-resources
- MeSH
- Emulsions * MeSH
- Erythrocytes drug effects MeSH
- Ethylamines chemistry MeSH
- Fluorocarbons chemistry MeSH
- Hydrocarbons, Fluorinated chemistry MeSH
- Galactose adverse effects analogs & derivatives chemical synthesis MeSH
- Humans MeSH
- Methylamines chemistry MeSH
- Morpholines chemistry MeSH
- Poloxamer chemistry MeSH
- Sorbitol adverse effects analogs & derivatives chemical synthesis MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Emulsions * MeSH
- Ethylamines MeSH
- Fluorocarbons MeSH
- Hydrocarbons, Fluorinated MeSH
- Galactose MeSH
- Methylamines MeSH
- Morpholines MeSH
- perfluorodecalin MeSH Browser
- Poloxamer MeSH
- Sorbitol MeSH
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.
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