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The use of archaeal lipids and their artificial analogues, also known as bolalipids, represents a promising approach for the stabilization of classical lipid vesicles for oral application. In a previous study, we investigated the mixing behavior of three single-chain alkyl-branched bolalipids  PC-C32(1,32C n )-PC  ( n  = 3, 6, 9) with either saturated or unsaturated phosphatidyl-cholines. We proved, that the bolalipids  PC-C32(1,32C6)-PC  and  PC-C32(1,32C9)-PC  show miscibility with 1-palmitoyl-2-oleoyl- sn -glycero-3-phosphocholine (POPC) and 1,2-dioleoyl- sn -glycero-3-phosphocholine (DOPC). In the present work, we extended our vesicle system to natural lipid mixtures using phosphatidylcholine from soy beans, and we investigated the effect of incorporated bolalipids on the integrity of these mixed liposomes (bolasomes) in different gastrointestinal fluids using a dithionite assay and a calcein release assay in combination with particle size measurements. Finally, we also studied the retention of calcein within the bolasomes during freeze-drying. As a main result, we could show that in particular  PC-C32(1,32C6)-PC  is able to increase the stability of bolasomes in simulated gastric fluid—a prerequisite for the further use of liposomes as oral drug delivery vehicles.

Bolalipid-Doped Liposomes: Can Bolalipids Increase the Integrity of Liposomes Exposed to Gastrointestinal Fluids?