The novel water soluble peripherally and non-peripherally tetra piperidine substituted phthalocyanines: Synthesis, characterization, DNA cleavage properties

The phthalonitrile compounds 4-(3-(piperidin-1-ylmethyl)phenoxy)phthalonitrile (3a) and 3-(3-(piperidin-1-ylmethyl)phenoxy)phthalonitrile (3b), peripherally tetra substituted zinc(II) (4a) and copper(II) (5a) phthalocyanines and their quaternized water soluble derivatives (6a) and (7a), nonperipherally tetra substituted zinc(II) (4b) and copper(II) (5b) phthalocyanines and their quaternized water soluble derivatives (6b) and (7b) were synthesized for the first time in this work. These novel compounds were characterized with FT-IR, H-1-NMR, C-13-NMR, UV-Vis and mass spectroscopy. The cleavage properties of the novel water soluble zinc (II) (6a, 6b) and copper (II) (7a, 7b) phthalocyanines were examined by agarose gel electrophoresis. No prominent DNA cleavage was observed for the various concentrations of compounds (6a, 6b, 7a and 7b) without irradiation while the novel water soluble peripherally and non-peripherally tetra piperidine substituted zinc (II) (6a and 6b) phthalocyanines had significant cleavage effects to plasmid DNA with irradiation. In the oxidative cleavage studies, (6b) had more remarkable cleavage in the presence of H2O2, AA and ME than tested other compounds. All of these results demonstrated that (6b) may act as a photosensitizer for photodynamic therapy due to the generation of DNA damage with irradiation. (C) 2019 Elsevier B.V. All rights reserved.