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Issue 18, 2017
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Assessment of the relevance of GaPc substituted with azido-polyethylene glycol chains for photodynamic therapy. Design, synthetic strategy, fluorescence, singlet oxygen generation, and pH-dependent spectroscopic behaviour

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Abstract

A new efficient synthetic route was used to obtain symmetrically and asymmetrically substituted gallium(III) phthalocyanines (5-GaCl and 6-GaCl) containing azido groups with chlorine atoms at axial positions, using corresponding ZnPc derivatives (5-Zn and 6-Zn) as precursors. The photophysical and photochemical properties—fluorescence, singlet oxygen generation, and photodegradation—of 5-GaCl and 6-GaCl were compared with that of 5-Zn and 6-Zn. Their pH-sensitive spectral changes were also investigated in detail, as tumours are more acidic than healthy tissues. Their amphiphilicity, quantified by their partition coefficient, appeared suitable for biological applications. 5-GaCl and 6-GaCl exhibited higher photodynamic potential than unsubstituted gallium(III) phthalocyanine, suggesting potential to be used as a photodynamic therapy agent.

Graphical abstract: Assessment of the relevance of GaPc substituted with azido-polyethylene glycol chains for photodynamic therapy. Design, synthetic strategy, fluorescence, singlet oxygen generation, and pH-dependent spectroscopic behaviour

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Publication details

The article was received on 26 Apr 2017, accepted on 04 Aug 2017 and first published on 04 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ01390F
Citation: New J. Chem., 2017,41, 10027-10036
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    Assessment of the relevance of GaPc substituted with azido-polyethylene glycol chains for photodynamic therapy. Design, synthetic strategy, fluorescence, singlet oxygen generation, and pH-dependent spectroscopic behaviour

    V. Koç, S. Z. Topal, D. Aydın Tekdaş, Ö. D. Ateş, E. Önal, F. Dumoulin, A. G. Gürek and V. Ahsen, New J. Chem., 2017, 41, 10027
    DOI: 10.1039/C7NJ01390F

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