A Sn(IV) porphyrin with mitochondria targeting properties for enhanced photodynamic activity against MCF-7 cells

Two readily synthesized Sn(IV) porphyrins (SnP, SnPH) have been prepared with and without the cationic triphenylphosphonium moiety (TPP+), which have high singlet oxygen quantum yields (ca. 0.72) and long triplet state lifetimes. The Sn(IV) porphyrin with a TPP+ moiety (SnPH) exhibits favorable photodynamic activity against MCF-7 cells with IC50 values of 2.9 mu M. SnPH exhibits higher cellular uptake than SnP in MCF-7 cells. A Rhodamine 123 (Rh123) assay showed that SnPH targets mitochondria and induces apoptosis by generating reactive oxygen species. The results demonstrate that this structural modification strategy merits further in-depth study.

Automated summary

Two readily synthesized Sn(IV) porphyrins with and without a cationic triphenylphosphonium moiety (TPP+) were prepared in this study. The Sn(IV) porphyrin with a TPP+ moiety exhibited favorable photodynamic activity against MCF-7 cells and showed higher cellular uptake compared to the one without TPP+. Further investigation suggested that this structural modification strategy deserves further exploration.