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    Öğe
    New peripherally and non-peripherally tetra-substituted water soluble zinc phthalocyanines: Synthesis, photophysics and photochemistry
    (Elsevier Science Sa, 2015) Cakir, Volkan; Cakir, Dilek; Piskin, Mehmet; Durmus, Mahmut; Biyiklioglu, Zekeriya
    The synthesis and photochemical properties of peripherally and non-peripherally 1,3-bis[3-(dimethy-lamino)phenoxy]prop-2-oxy tetra-substituted zinc phthalocyanines (2a and 3a) and their quaternized derivatives (2b and 3b) were reported in this study. Photochemical properties of quaternized ionic zinc (II) phthalocyanines (2b and 3b) were investigated in both dimethyl sulfoxide (DMSO) and aqueous solutions, while non ionic derivatives were only studied in DMSO. The quaternized compounds exhibit excellent solubility in water, making them potential photosensitizers for use in photodynamic therapy (PDT) of cancer. This study also showed that the water-soluble quaternized Zn(II) phthalocyanines strongly bind to blood plasma proteins such as bovine serum albumin (BSA). On the other hand, the interactions of the novel water soluble phthalocyaines with DNA were also examined. (C) 2015 Elsevier B.V. All rights reserved.
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    Öğe
    Water soluble peripheral and non-peripheral tetrasubstituted zinc phthalocyanines: Synthesis, photochemistry and bovine serum albumin binding behavior
    (Elsevier, 2014) Cakir, Volkan; Cakir, Dilek; Piskin, Mehmet; Durmus, Mahmut; Biyiklioglu, Zekeriya
    The new peripherally and non-peripherally tetra-1,3-bis[3-(diethylamino)phenoxy]propan-2-ol substituted zinc(II) phthalocyanine complexes (2a and 3a) and their quaternized amphiphilic derivatives (2b and 3b) have been synthesized and characterized using UV-vis, FT-IR, H-1-NMR, C-13-NMR, MS spectroscopic data and elemental analysis for the first time. The quaternized complexes (2b and 3b) show excellent solubility in water and DMSO which makes them potential photosensitizers for use in photodynamic therapy (PDT) of cancer. The photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of these novel phthalocyanines are investigated in dimethylsulfoxide (DMSO) for non-quaternized complexes and in DMSO, phosphate buffered solution (PBS) or PBS+triton X-100 (TX) solution for quaternized complexes. In this study, the effects of the aggregation of the molecules, quaternization, position of the substituents (peripherally or non-peripherally) and nature of the solvents (DMSO, PBS or PBS+triton X-100) on the photochemical parameters of the zinc (II) phthalocyanines are also reported. In addition, a spectroscopic investigation of the binding behavior of the quaternized zinc(II) phthalocyanine complexes to bovine serum albumin (BSA) is also presented in this work. (C) 2014 Elsevier B.V. All rights reserved.