Novel perfluoroalkylated derivatives of D-galactopyranose and xylitol for biomedical uses. Hemocompatibility and effect on perfluorocarbon emulsions.
6-O-(4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxyheptyl)-, 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, and 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-d-galactopyranose (9, 10, and 11, resp.) were prepared by a two-step synthesis including the reaction of 1,2:3,4-di-O-isopropylidene-alpha-d-galactopyranose with 2-[(perfluoroalkyl)methyl]oxiranes under catalysis with BF(3).Et(2)O. Similarly, 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-dl-xylitol (18, 19, and 20, resp.) were prepared by a two-step synthesis from the corresponding 1,2:3,4-di-O-isopropylidene-dl-xylitol. Most of the both types of fluoroalkylated carbohydrate derivatives 9-11 and 18-20 generally displayed very low level of hemolytic activity and excellent co-emulsifying properties on testing on perfluorodecalin-Pluronic F-68 microemulsions.
Církva
Vladimír
V
Department of Organic Chemistry, Institute of Chemical Technology Prague, Technická 5, 166 28 Prague, Czech Republic.
Polák
Radek
R
Paleta
Oldrich
O
Kefurt
Karel
K
Moravcová
Jitka
J
Kodícek
Milan
M
Forman
Stanislav
S
D000475:Alkenes; D000478:Alkylation; D002236:Carbohydrate Conformation; D004655:Emulsions; D004912:Erythrocytes / Q000502:physiology*; D005466:Fluorocarbons; D005690:Galactose / Q000031:analogs & derivatives* / Q000097:blood / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D007202:Indicators and Reagents; D008958:Models, Molecular; D014993:Xylitol / Q000031:analogs & derivatives* / Q000097:blood / Q000138:chemical synthesis / Q000737:chemistry*
D000475:Alkenes; D004655:Emulsions; D005466:Fluorocarbons; D007202:Indicators and Reagents; C013658:propylene; D014993:Xylitol; D005690:Galactose