Synthesis and Stability Studies of α,α‐Difluoro Ester Phospholipids

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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.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Issue number33
Pages (from-to)6656-6661
Publication statusPublished - 2012


  • Synthetic methods
  • Medicinal chemistry
  • Nanoparticles
  • Drug delivery
  • Phospholipids
  • Liposomes

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