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Issue 12, 2016
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Anionic hexadeca-carboxylate tetrapyrazinoporphyrazine: synthesis and in vitro photodynamic studies of a water-soluble, non-aggregating photosensitizer

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Abstract

A sodium salt of zinc tetrapyrazinoporphyrazine bearing eight 3,5-dicarboxylatophenyl substituents (1) was synthesized. The presence of sixteen negative charges in a rigid arrangement on the periphery of the macrocycle inhibited its aggregation in water or buffers at pH > 5.8. Strong aggregation was, however, observed in buffers at pH < 4.8 due to the protonation of carboxylate functions. Fluorescence microscopy revealed that the compound localized to lysosomes and endosomes in cells. The compound's photodynamic activity on HeLa cancer cells (IC50 = 5.7 ± 1.1 μM) was found to be influenced by both pH and interactions with serum proteins. This was demonstrated with a detailed in vitro study based on the inhibition of vacuolar H+-ATPase using bafilomycin A1, which increased the intracellular fluorescence of 1. Compound 1 also formed interactions with serum proteins that partially quenched its excited states; however, they also protected the compound from self-aggregation at low pH.

Graphical abstract: Anionic hexadeca-carboxylate tetrapyrazinoporphyrazine: synthesis and in vitro photodynamic studies of a water-soluble, non-aggregating photosensitizer

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Publication details

The article was received on 04 Dec 2015, accepted on 13 Jan 2016 and first published on 15 Jan 2016


Article type: Paper
DOI: 10.1039/C5RA25881B
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2016,6, 10064-10077
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    Anionic hexadeca-carboxylate tetrapyrazinoporphyrazine: synthesis and in vitro photodynamic studies of a water-soluble, non-aggregating photosensitizer

    M. Machacek, J. Kollár, M. Miletin, R. Kučera, P. Kubát, T. Simunek, V. Novakova and P. Zimcik, RSC Adv., 2016, 6, 10064
    DOI: 10.1039/C5RA25881B

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