engleski

Liposome-incorporated Adamantyl Aminoguanidines as a Versatile Tool for Biomedical Applications

Over the past 40 years the adamantane structural motif has been used in medicinal chemistry [1] and several adamantane-containing compounds are in current clinical use.[2] On the other hand, guanidine-containing derivatives represent a very important class of biologically active compounds, not only as antimicrobial agents but also compounds such as dendritic guanidines which are used in the intracellular delivery of biologically significant cargos.[3] In the continuation of our study dealing with adamantane derivatives with a guanidine subunit [4] and investigations of liposomes as drug delivery systems as well as a model membrane, [5] we prepared a series of adamantyl aminoguanidines 1-6 (Figure 1) and characterized their liposome formulations. These compounds combine the membrane compatible features of adamantane moiety and favorable structural features of the cationic, guanidinium subunit. It was found that adamantyl aminoguanidines were successfully encapsulated into multilamellar liposomes and that the liposome stability and permeability was affected by the presence of these compounds. The studied adamantyl aminoguanidine derivatives incorporated into the lipid bilayer effectively recognized the complementary liposomes bearing the phosphate group on their surface. The adamantyl moiety can therefore serve as a molecular anchor in a lipid bilayer while the polar guanidinium head is exposed on the liposome surface, thus enabling successful interaction with membrane’s phospholipids and usage in various studies of molecular recognition processes.

adamantane; guanidine; liposomes; molecular recognition; drug delivery

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