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Preparation and characterization of supramolecular systems based on amphiphilic β-cyclodextrin vesicles and liposomes functionalized with adamantly guanidines for gene delivery

The aim of the present study was preparation and characterization of supramolecular systems with adamantyl guanidine for gene delivery. In the continuation of our study dealing with adamantyl guanidines and investigations of lipid-based nanovesicles as drug delivery systems1-3 we prepared and characterized functionalized supramolecular systems of adamantyl guanidines AG 1-5 with phosphatidylcholine liposomes, liposomes incorporating amphiphilic β-cyclodextrin (β-CD) derivative and cyclodextrin vesicles composed only from the amphiphilic β-CD derivative. Efficiency of incorporation of adamantyl guanidines into prepared supramolecular systems was measured spectrophotometrically, and the size and surface charge were determined by dynamic light scattering method. It was shown that all examined compounds were successfully incorporated into prepared supramolecular systems except compound AG5. The incorporation of adamantyl guanidines did not affect the size of prepared supramolecular systems but surface charge was significantly changed. Fluorescence correlation spectroscopy (FCS) was applied to examine the interactions between functionalized supramolecular systems and the Cy5- fluorescently labelled, double-stranded, 120 bp DNA (DNA120*). The obtained results have clearly demonstrated that the supramolecular systems with entrapped AG 1-4 present guanidinium groups on the surface of vesicles, which leads to interaction with DNA120* via guanidine-phosphate interaction. Also, it was shown that vesicles modified with adamantyl guanylhydrazones (AG 1-2) bind DNA more efficiently, for almost an order of magnitude than vesicles modified with adamantyl aminoguanidines (AG 3-4). Preliminary results have shown that prepared functional supramolecular systems strongly bind DNA and as such could be used in gene delivery.

adamantyl guanidine ; amphiphilic beta-cyclodextrine ; supramolecular complexes, liposomes, host-guest interaction ; fluorescence correlation spectroscopy ; gene delivery

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