Liposomes of enviroxime and phosphatidylcholine: definition of the drug-phospholipid interactions.

Interaction of the antiviral compound, enviroxime (E), with natural and synthetic phosphatidylcholines in organic and aqueous media was studied. Although insoluble in chloroform, E dissolved in chloroform solutions containing phosphatidylcholines. Solvation was directly related to the length of the fatty acid chains of the phospholipid. Proton spin resonance studies suggested an interaction of the fatty acid chains with the aromatic rings of E. Suspension of E-phosphatidylcholine mixtures of molar ratios up to 0.7:1.0 in aqueous media resulted in the formation of multilamellar liposomes. Liposomes containing E were more stable permeability barriers than those prepared with phospholipid alone, a property previously observed with cholesterol. Competition experiments suggested that E bound to the same sites in lipid bilayers as does cholesterol. These data indicate that E is incorporated into lipid bilayers of liposomes and that it alters the physical properties of the liposomes in a manner similar to that of cholesterol.