SYNTHETIC GLYCOLIPIDS WITH CUSTOMISED DISTANCE BETWEEN LIPID AND GLYCO PARTS

摘要

Glycolipids are capable to spontaneous insertion into cell membranes. The application of such molecules is often limited by requirement to use organic solvents for maintain them in a solution-phase suitable for insertion and this can limit their compatibility with live cells. Recently synthetic glycolipid-like constructs, which have a spacer between a synthetically friendly lipid (as a rule, dioleoyl phosphatidylethanolamine, DOPE) and the glycan head have been constructed. These constructs are now known as Function-Spacer-Lipid constructs (FSLs). All FSLs have been designed to disperse as a solution directly in organic solvents free water, saline and biological media. FSLs posses linear 1 or branched 2 structure (Scheme 1, 1-2). Like natural glycolipids, all FSLs found to insert easily into cell membranes. Spacer (S) as part of FSLs is no less important than parts F and L, we usually use CMG 3-4. They: 1) distances the glycan from the cell membrane to the required distance, 2) increases dispersibility in water, 3) can work in stealth mode, because they do not interact with blood components. Changing the amount of tripeptide blocks in CMG we can variate the distance between F and L moieties in an interval up to 20 nm.