Optical modulation of cell nucleus penetration and singlet oxygen release of a switchable platinum complex

The activation of anticancer molecules with visible light constitutes an elegant strategy to target tumors and to improve the selectivity of treatments. In this context, we report here a visible-light activatable bis-platinum complex (DHP-Pt) incorporating an organic photo-switchable ligand based on the dimethyldihydropyrene moiety. Illumination of this metal complex with red light (660 nm) under air readily produces the corresponding endoperoxide form (CPDO-Pt). These two metal complexes exhibit different DNA binding properties and, more importantly, we show that only the photogenerated CPDO-Pt is able to penetrate into cancer cell nuclei, where it is then capable of releasing cytotoxic singlet oxygen. This study represents the first proof-of-concept showing that dimethyldihydropyrene derivatives can be used to transport and deliver singlet oxygen into cancer cell nuclei upon visible-light activation.