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Photodynamic properties of aza-analogues of phthalocyanines

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Abstract

The replacement of benzene rings in phthalocyanines with various N-heterocycles produces a number of aza-analogues, azaphthalocyanines. This review summarizes their properties important for photodynamic therapy with a focus on (but not limited to) the most studied derivatives, i.e. tetrapyrazinoporphyrazines, tetra(2,3-pyrido)porphyrazines and tetra(3,4-pyrido)porphyrazines. Specifically, the spectral properties in both organic and aqueous solutions are discussed, with an emphasis on the prevention of undesirable aggregation, which typically leads to a loss of the photodynamic effects. Photophysical properties, such as the quantum yield of singlet oxygen production, may provide insights into the potential of azaphthalocyanines to cause cell death, whereas fluorescence quantum yields may refer to their role in cancer visualization. The main part of this review summarizes published results on the in vitro evaluation of these aza-analogues for anticancer, antifungal, and antimicrobial treatments as well as their interactions with biological materials.

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Acknowledgments

This work was supported by the Czech Science Foundation (grant no. 17-19094S). The authors would like to thank P. Stuzhin and T. Nyokong for providing the source spectral data for some compounds.

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  1. Faculty of Pharmacy in Hradec Kralove, Charles University, Akademika Heyrovskeho 1203, Hradec Kralove, 50005, Czech Republic

    Miroslav Miletin, Petr Zimcik & Veronika Novakova

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  1. Miroslav Miletin
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  2. Petr Zimcik
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Correspondence to Petr Zimcik or Veronika Novakova.

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Miletin, M., Zimcik, P. & Novakova, V. Photodynamic properties of aza-analogues of phthalocyanines. Photochem Photobiol Sci 17, 1749–1766 (2018). https://doi.org/10.1039/c8pp00106e

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