The host-guest complexation of a tailored Si(IV) phthalocyanine with supramolecular β-cyclodextrin vesicles (CDV) was studied, revealing a reduced aggregation of the photoactive center upon binding to the CDV, even in aqueous environments. For this purpose, a photosensitizing unit axially decorated with one adamantyl group and one pyridinium moiety on the other side was obtained by two successive click reactions on a bis-azido-functionalized derivative of Si(IV) phthalocyanine. To evaluate its potential as a photosensitizer against antibiotic-resistant bacteria, comparative studies of the photophysical properties including absorption and emission spectroscopy, lifetimes as well as fluorescence and singlet oxygen quantum yields were determined for the Si(IV) phthalocyanine alone and upon self-assembly on the CDV surface. In vitro phototoxicity against the methicillin-resistant Staphylococcus aureus (MRSA) USA300 was evaluated, showing an almost complete inactivation.
Keywords: MRSA; cyclodextrin vesicle; phthalocyanine; self-assembly; singlet oxygen.