title: 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: 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.
authors.affiliation: Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, Gebze, 41400, Kocaeli, Turkey.
authors.forename: Sinem
authors.initials: S
authors.lastname: Tuncel
authors.forename: Fabienne
authors.initials: F
authors.lastname: Dumoulin
authors.forename: Jürgen
authors.initials: J
authors.lastname: Gailer
authors.forename: Melani
authors.initials: M
authors.lastname: Sooriyaarachchi
authors.forename: Devrim
authors.initials: D
authors.lastname: Atilla
authors.forename: Mahmut
authors.initials: M
authors.lastname: Durmuş
authors.forename: Denis
authors.initials: D
authors.lastname: Bouchu
authors.forename: Huguette
authors.initials: H
authors.lastname: Savoie
authors.forename: Ross W
authors.initials: RW
authors.lastname: Boyle
authors.forename: Vefa
authors.initials: V
authors.lastname: Ahsen
mesh_terms: D000042:Absorption; D000818:Animals; D001798:Blood Proteins / Q000378:metabolism*; D002417:Cattle; D015195:Drug Design; D019073:HT29 Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D054833:Isoindoles; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D055668:Photochemical Processes; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D011092:Polyethylene Glycols / Q000737:chemistry*; D011485:Protein Binding; D012710:Serum Albumin, Bovine / Q000378:metabolism; D026082:Singlet Oxygen / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry*; D017967:Zinc Compounds
chemical_list: D001798:Blood Proteins; D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D017967:Zinc Compounds; D014867:Water; C052159:Zn(II)-phthalocyanine; D026082:Singlet Oxygen; D012710:Serum Albumin, Bovine; D011092:Polyethylene Glycols