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A peptide-conjugated zinc(ii) phthalocyanine has been prepared which can selectively bind to the epidermal growth factor receptor of cancer cells and induce high cytotoxicity upon illumination.

Inverse-electron-demand Diels–Alder reaction of a 1,2,4,5-tetrazine-substituted boron dipyrromethene with a biotin-conjugated trans-cyclooctene results in site-specific activation of the photoactivity of the former photosensitiser.

Two dual stimuli-activated photosensitizers were developed, in which two or three glutathione (GSH)-responsive 2,4dinitrobenzenesulfonate (DNBS)-substituted zinc(II) phthalocyanine units were connected via one or two cathepsin B-cleavable Gly-Phe-Leu-Gly peptide linker(s). These dimeric and trimeric phthalocyanines were fully quenched in the native form due to the photoinduced electron transfer to the DNBS substituents and the self-quenching of the phthalocyanine units. In the presence of GSH and cathepsin B, or upon internalization into A549 and HepG2 cancer cells, these probes were activated through the release of free phthalocyanine units. The intracellular fluorescence intensity was increased upon post-incubation with GSH ester or reduced upon pre-treatment with a cathepsin B inhibitor. Upon light irradiation, these photosensitizers became highly cytotoxic with IC 50 values of 0.21−0.39 μM. The photocytotoxicity was also dependent on the intracellular GSH and cathepsin B levels. The results showed that these conjugates could serve as smart photosensitizers for targeted photodynamic therapy.

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