Design, synthesis, and properties of neoglycolipids based on ethylene glycoles conjugated with lactose as components of targeted delivery systems of biologically active compounds

Abstract

Synthesis has been developed of a series of new aliphatic lactose derivatives as components of liposomal targeted delivery systems distinguished by the length and the number of aliphatic chains and also by the length of the spacer fragment. The structure of compounds synthesized has been established by means of 1 H NMR spectroscopy.

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

“…314−316 A series of Lac-based neoglycolipids with varying ethylene glycol aglycones were prepared, and a representative, 43, is shown in Figure 7. 315,316 Fuc derivatives with ethylene glycol linkers, such as 44, Various N-oxyamide-linked neoglycolipids (45) were prepared as a way to improve metabolic stability and hydrogenbonding properties of the glycolipid. 318 Other synthetic neoglycolipid probes have been generated via oxime ligation of the reducing end with an aminooxy-functionalized lipid, and oxime linkages are hydrolytically stable under physiological conditions.…”

“…Amphiphilic Lac-based neoglycolipids differing in the length of the spacer fragment, or the aliphatic chain, have served as components of targeted drug-delivery systems. − A series of Lac-based neoglycolipids with varying ethylene glycol aglycones were prepared, and a representative, 43 , is shown in Figure . , Fuc derivatives with ethylene glycol linkers, such as 44 , were synthesized by Faivre et al and assessed for their potential as amphiphilic drug carriers. The anomeric configuration of Fuc influenced the organization of monolayers but not the fluidity of liposomes …”