Photophysical properties and photocytotoxicity of novel phthalocyanines - potentially useful for their application in photodynamic therapy |
| |
Authors: | Tomasz GoslinskiTomasz Osmalek Krystyna KonopkaMarcin Wierzchowski Piotr Fita Jadwiga Mielcarek |
| |
Institution: | a Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland b Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland c Department of Biomedical Sciences, University of the Pacific, Arthur A. Dugoni School of Dentistry, San Francisco, USA d Department of Physical Chemistry, University of Geneva, 30 quai Ernest-Ansermet, CH-1211 Geneva 4, Switzerland e Institute of Experimental Physics, Faculty of Physics, University of Warsaw, Hoza 69, 00-681 Warsaw, Poland |
| |
Abstract: | Two novel zinc(II) phthalocyanines bearing non-peripheral ester-alkyloxy substituents (Pc-4 and Pc-5) were synthesized, by a two-step procedure starting from 2,3-dicyanohydroquinone. Both sensitizers show promising photophysical properties, including solvatochromic study, qualitative evaluation of emission, aggregation behavior and singlet oxygen generation. It was proven that the photodynamic activity of the compounds studied depends on the molecular oxygen level. Comparison of the quantum yields of singlet oxygen generation as well as the oxidation rate constants using 1,3-diphenylisobenzofurane before and after deaeration proved the photodynamic effect of Pc-4 and Pc-5 to be governed by the photosensitization mechanism II. Changes in the quantities of the compounds exposed to irradiation were also estimated. Upon their exposure to light the changes in intensity of the Q band were monitored. The photodecomposition of Pc-4 and Pc-5 in DMSO or DMF solutions was found to proceed according to the first order kinetic reaction in two stages.The photosensitizing effect of Pc-4 in HSC-3 cells was significantly lower than that of ZnPc. Pc-4 was ineffective at 0.1 μM, while a low, approx. 15% photocytotoxicity was observed at 5 μM, at a distance of 5 and 10 cm. The efficacy of Pc-4 in photokilling of cultured cells is affected by hydrophobicity and the aggregation status of the photosensitizer. |
| |
Keywords: | Photocytotoxicity Photosensitizer Phthalocyanine Singlet oxygen Solvatochromic effect PDT |
本文献已被 ScienceDirect 等数据库收录! |
|