Introducing a new Element - Fluorine -Into the Liposomal Membrane

Abstract

Amphiphiles with fluorinated hydrophobic tails constitute new, distinctively different components for membranes, liposomes, tubules and other self-aggregated supramolecular systems. Fluorinated liposomes (F-liposomes) can also be obtained from combinations of standard phospholipids with mixed fluorocarbon-hydrocarbon amphiphiles. The fluorinated moieties are considerably more hydrophobic than their hydrocarbon counterparts; they have also a larger cross section, are more rigid, and are lipophobic as well. As a result, fluorinated amphiphiles show enhanced propensity to self-assemble, lead to increased membrane ordering and stability, and their stacking creates a teflon-like repellent film within the liposomal membrane, which can significantly increase drug encapsulation stability. The fluorinated chains also impact on behavior in biological media and particle recognition, as exemplified by reduced hemolytic and detergent activity, prolonged intravascular persistence, or slower enzymatic hydrolysis of phospholipids.