A [5]Rotaxane-Based Photosensitizer for Photodynamic Therapy

A [5]rotaxane was synthesized through a catalytically self-threading reaction in which CB6 serves as a macrocycle and acts as a catalyst for the 1,3-dipolar cycloaddition reaction between the alkyne substituted porphyrin core and azide functionalized stopper groups by forming triazole. Application of this rotaxane as a photosensitizer in photodynamic therapy against cancer cells and in bacteria inactivation have also been demonstrated. This photosensitizer has an excellent water solubility and remains stable in biological media at physiological pH (7.4) for prolonged times. It has the ability to generate singlet oxygen efficiently; while it shows no dark cytotoxicity up to 300 mu m to the MCF7 cancer cell line, it is photocytotoxic even at 2 mu m and reduces the cell viability to around 70 % when exposed to white light. It also displays light-triggered biocidal activity both against gram-negative bacteria (Escherichia coli, E. coli) and gram-positive bacteria (Bacillus subtilis). Upon white light irradiation for 1 min with a flux of 22 mW/cm(2) of E. coli suspension incubated with [5]rotaxane (3.5 mu m), a killing efficiency of 96 % is achieved, whereas in the dark the effect is recorded as only around 9 %.