SATURATED AND POLYMERIZABLE AMPHIPHILES WITH FLUOROCARBON CHAINS. INVESTIGATION IN MONOLAYERS AND LIPOSOMES.

Article abstract of DOI:10.1021/ja00337a005

The synthesis and characterization of several saturated and polymerizable amphiphiles with fluorocarbon chains are described. Monolayers of lipids containing fluorocarbon chains are more stable than those formed from their hydrocarbon counterparts. The creation of phase-separated monolayers and liposomes is possible when the membrane is composed of a mixture of lipids containing hydrocarbon chains and lipids containing fluorocarbon chains. Phase separation even occurs when the two lipids bear the same head group. Complete phase separation of a natural lipid (DMPC) and a lipid with fluorocarbon chains, 1, could be demonstrated in liposomes by using freeze-fracture electron microscopy. Phase separation was even confirmed when the percentage of the fluorocarbon amphiphile was as low as 5 mol%. The polymerization behavior of unsaturated amphiphiles with fluorocarbon chains was investigated in monolayers and liposomes.