Synthetic Outer Membrane Vesicles Bearing Tn Antigen

Abstract

: N‐alkyl‐thio glycolipids (TGL) are proposed as fundamental components in the production of synthetic outer membrane vesicles (S‐OMVs). A small but representative library of glycolipids was prepared by thiol‐ene coupling (TEC), using unprotected thiols in acceptable to good yields (63‐96%). Multilamellar giant vesicles (GVs) of varying sizes were assembled from mixtures of TGL and 1‐palmitoyl‐2‐oleoyl‐sn‐glycero‐3‐phosphate (POPC). Our results mark an important advancement for the development of synthetic anticancer vaccines, supramolecular adjuvants and drug delivery systems based on glycolipid/phospholipid formulations (10 % mol/mol in 0.1 mm solution).