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

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

doi:10.1039/C0DT01260B

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

Sinem Tuncel,^a Fabienne Dumoulin,^a Jürgen Gailer,^b Melani Sooriyaarachchi,^b Devrim Atilla,^a Mahmut Durmuş,^a Denis Bouchu,^c Huguette Savoie,^d Ross W. Boyle^d and Vefa Ahsen*^a

Author affiliations

* Corresponding authors

^a Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, Gebze, Kocaeli, Turkey

^b Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, AB, Canada

^c Centre Commun de Spectrométrie de Masse UMR 5246, CNRS-Université Claude Bernard Lyon 1, Université de Lyon, Bâtiment Curien, 43, bd du 11 Novembre, 69622 Villeurbanne Cedex, France

^d Department of Chemistry, University of Hull, Kingston-upon-Hull, East Yorkshire, UK

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.

Dalton Transactions

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements