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Issue 34, 2017
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A cell-selective glutathione-responsive tris(phthalocyanine) as a smart photosensitiser for targeted photodynamic therapy

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Abstract

A biotin-conjugated disulfide-linked tris(phthalocyanine) has been synthesised and characterised. As shown by electronic absorption and steady-state fluorescence spectroscopy methods, the compound remains non-aggregated in N,N-dimethylformamide, but is significantly aggregated in phosphate buffered saline with 1% Cremophor EL. The reduction in fluorescence intensity and singlet oxygen generation efficiency as compared with the monomeric counterpart suggests that the tris(phthalocyanine) exhibits an excellent self-quenching effect, particularly in an aqueous medium. Upon interaction with glutathione, both the fluorescence emission and singlet oxygen production can be restored as a result of the cleavage of the disulfide linkages, thereby releasing the phthalocyanine units and reducing their aggregation and self-quenching effects. With a biotin moiety, this tris(phthalocyanine) is preferentially taken up by the biotin-receptor-positive HeLa cells and activated by the intracellular glutathione, resulting in fluorescence recovery and photocytotoxicity with an IC50 value of 0.68 μM. This compound can therefore act as a dual functional photosensitiser.

Graphical abstract: A cell-selective glutathione-responsive tris(phthalocyanine) as a smart photosensitiser for targeted photodynamic therapy

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Publication details

The article was received on 07 Jun 2017, accepted on 24 Jul 2017 and first published on 25 Jul 2017


Article type: Paper
DOI: 10.1039/C7DT02086D
Citation: Dalton Trans., 2017,46, 11223-11229
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    A cell-selective glutathione-responsive tris(phthalocyanine) as a smart photosensitiser for targeted photodynamic therapy

    S. Y. S. Chow, S. Zhao, P. Lo and D. K. P. Ng, Dalton Trans., 2017, 46, 11223
    DOI: 10.1039/C7DT02086D

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