Phthalocyanine−Polyamine Conjugates as Highly Efficient Photosensitizers for Photodynamic Therapy

A series of silicon(IV) phthalocyanines substituted axially with different polyamine moieties have been prepared. Their fluorescence quantum yields (ΦF = 0.03−0.08) in N,N-dimethylformamide are low because of reductive quenching by the amino moieties. The values are significantly increased in aqueous media (ΦF = 0.12−0.21) as a result of protonation of the amino substituents. All the compounds are highly photocytotoxic against human colon adenocarcinoma HT29 cells and Chinese hamster ovary cells with IC50 values as low as 1.1 nM. Flow cytometric studies of two selected compounds (2 and 5) against HT29 cells have shown that they induce apoptosis extensively. As shown by confocal microscopy, these two compounds also show high affinity toward the lysosomes, but not the mitochondria, of the cells. Their in vivo photodynamic activity has also been investigated using HT29 tumor bearing nude mice. Both of them can effectively inhibit the growth of the tumor without causing apparent injury to the liver of the mice.