Pedersen, Palle Jacob1; Andresen, Thomas Lars3; Clausen, Mads Hartvig1
1 Department of Chemistry, Technical University of Denmark2 Center for Nanomedicine and Theranostics, Center, Technical University of Denmark3 Department of Micro- and Nanotechnology, Technical University of Denmark4 Colloids and Biological Interfaces, Department of Micro- and Nanotechnology, Technical University of Denmark5 Organic Chemistry, Department of Chemistry, Technical University of Denmark
The synthesis of two new α,α‐difluoro ester phospholipid conjugates is described and the stability of their liposomal formulations in three different aqueous buffers (pH 4.5, 7.5 and 8.5) has been investigated. The studies confirmed that α,α‐difluoro esters are much more prone to hydrolysis when positioned close to the hydrophilic head group of phospholipids than when the functionality is placed in the lipophilic part of the bilayer in liposomes. This observation lends further support to the concept of protecting hydrolysable functionalities by formulation as part of the membrane of liposomes.
European Journal of Organic Chemistry, 2012, Vol 2012, Issue 33, p. 6656-6661
Synthetic methods; Medicinal chemistry; Nanoparticles; Drug delivery; Phospholipids; Liposomes