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A new family of perylenediimide (PDI) silver and copper complexes has been successfully synthesized by reacting ortho- and bay-substituted (dipyrid-2′,2″-ylamino)perylenediimide ligands with metal phosphine fragments. The coordination of the metal center did not reveal a significant effect on the photophysical properties, which are mainly due to the PDI ligands, and in some cases quenching of the luminescence was observed. The antiproliferative effect of the free perylenediimide ligands and the metalloPDI complexes against the cervix cancer cell line HeLa was determined by MTT assay. The free perylenediimide ligands exhibited a moderate cytotoxic activity, but the coordination of silver or copper to the dypyridylamino fragment greatly enhanced the activity, suggesting a synergistic effect between the two fragments. In attempts to elucidate the cellular biodistribution of the PDIs and the complexes, a colocalization experiment using specific dyes for the lysosomes or mitochondria as internal standards revealed a major internalization inside the cell for the metal complexes, as well as a partial mitochondrial localization.

Perylenediimes (PDIs) are very interesting compounds due to their outstanding electrooptical properties, high fluorescence quantum yields, and huge versatility in their synthetic chemistry. Although PDIs are mainly used in optoelectronic applications, the number of biological studies using PDIs has been growing in the last few years. Here, we report on the synthesis and biological studies of two new families of PDIs as phototherapeutic agents. (Figure 1: a) Imidazolium-PDI, b) [AgPy2(PPh3)]-PDI). Thus, we have prepared water-soluble PDIs based on imidazolium salts as photosensitizes to generate singlet oxygen (1O2), which plays a key role in photodynamic therapy. Internalization and cytotoxicity assays were carried out in HeLa and SHSY5Y human neuroblastoma cells lines. On the other hand, taking advantage of the medicinal potential of some metals, we have synthesized new PDIs linked to silver and copper complexes to study their behavior as metallodrugs. Biological assays were also carried out in HeLa cells line.