Novel amphiphilic fluoroalkylated derivatives of xylitol, D-glucose and D-galactose for medical applications: hemocompatibility and co-emulsifying properties

Carbohydr Res. 2002 Nov 29;337(24):2411-8. doi: 10.1016/s0008-6215(02)00287-2.

Abstract

1-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluorononyl)xylitol 6 was synthesized as a novel standard compound for the assessment of hemocompatibility and co-emulsifying properties in microemulsions for biomedical uses. 3-O-(1,1,2,4,4,5,7,7,8,8,9,9,9-Tridecafluoro-5-trifluoro-methyl-3,6-dioxanonyl)-D-glucose 9 and 6-O-(1,1,2,4,4,5,7,7,8,8,9,9,9-tridecafluoro-5-trifluoromethyl-3,6-dioxanonyl)-D-galactose 12 were synthesized by nucleophilic addition of protected carbohydrates to perfluorinated vinyl oligoether. Biological tests revealed very good hemocompatibility and co-emulsifying properties for the amphiphiles 6, 9 and 12.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis*
  • Emulsions
  • Erythrocytes
  • Excipients
  • Fluorocarbons / chemical synthesis*
  • Galactose / analogs & derivatives
  • Glucose / analogs & derivatives
  • Humans
  • Materials Testing
  • Monosaccharides / chemical synthesis*
  • Surface-Active Agents / chemical synthesis*
  • Xylitol / analogs & derivatives

Substances

  • Biocompatible Materials
  • Emulsions
  • Excipients
  • Fluorocarbons
  • Monosaccharides
  • Surface-Active Agents
  • Glucose
  • Xylitol
  • Galactose