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A set of highly water-soluble tetraethyleneglycol-substituted Zn(ii) phthalocyanines: synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity

Gailer, Juergen; Durmus, Mahmut; Tuncel, Sinem; Dumoulin, Fabienne; Gailer, Jürgen; Sooriyaarachchi, Melani; Atilla, Devrim; Durmuş, Mahmut; Bouchu, Denis; Savoie, Huguette; Boyle, Ross W.; Ahsen, Vefa

Authors

Juergen Gailer

Mahmut Durmus

Sinem Tuncel

Fabienne Dumoulin

Jürgen Gailer

Melani Sooriyaarachchi

Devrim Atilla

Mahmut Durmuş

Denis Bouchu

Huguette Savoie

Vefa Ahsen



Abstract

Three Zn(II) phthalocyanines substituted by hydroxyl-terminated tetraethylene glycol chains have been synthesized. In order to evaluate the potential of these highly water-soluble phthalocyanines as type II-photosensitisers for photodynamic therapy, their structure-activity relationship was assessed by determining relevant photophysical and photochemical properties, such as their aggregation behaviour in aqueous buffers, their fluorescence properties and their efficiency with regard to the generation of singlet oxygen. In addition, evidence for a negligible interaction with plasma proteins in undiluted human plasma was obtained using a recently developed bioanalytical method and compared with the fluorescence quenching approach. These results combined with in vitro data regarding the phototoxicity of these phthalocyanines against HT-29 cancer cells provide evidence for the relevance of the non-peripherally substituted derivative for further in vivo investigations.

Journal Article Type Article
Publication Date Dec 31, 2011
Journal DALTON TRANSACTIONS
Print ISSN 1477-9226
Electronic ISSN 1477-9234
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 40
Issue 16
Pages 4067-4079
APA6 Citation Tuncel, S., Dumoulin, F., Gailer, J., Sooriyaarachchi, M., Atilla, D., Durmuş, M., …Ahsen, V. (2011). A set of highly water-soluble tetraethyleneglycol-substituted Zn(ii) phthalocyanines: synthesis, photochemical and photophysical properties, interaction with plasma proteins and in vitro phototoxicity. Dalton transactions : an international journal of inorganic chemistry / RSoC, 40(16), 4067-4079. https://doi.org/10.1039/c0dt01260b
DOI https://doi.org/10.1039/c0dt01260b
Keywords Inorganic Chemistry
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