Add time:07/20/2019         Source:sciencedirect.com

The triazol compound 3-methyl-4-(3-morpholinopropyl)-1H-1,2,4-triazol-5(4H)-one (3), phthalonitrile compound 4-(3-methyl-4-(3-morpholinopropyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phthalonitrile (5), peripherally tetra substituted zinc(II) (6) and copper(II) (7) phthalocyanines and their water soluble quaternized derivatives (6a) and (7a) were synthesized for the first time in this study. These novel compounds were characterized with FT-IR, 1H NMR, 13C NMR, UV–Vis and mass spectroscopy. The absorption titration, and thermal denaturation studies were preferred to investigate the interaction mode of the water soluble quaternized tetra substituted peripherally phthalocyanines zinc(II) (6a) and copper (II) (7a) with CT-DNA. 6a and 7a bound to CT-DNA with Kb values of 6.53 ± (0.04) × 104 M−1 and 1.14 ± (0.02) × 104 M−1, respectively. The observed ΔTm of CT-DNA with the compounds were elucidated as 7.55 °C and 5.75 °C. In addition, supercoiled pBR322 plasmid DNA was used to determine cleavage properties of the compounds by agarose gel electrophoresis. The compounds had no cleavage activities in the absence of oxidizing agents in the dark whereas; the both compounds had excellent photo cleavage activities in the absence and presence of oxidizing agents such as H2O2, ME and AA. The results of electrophoresis indicated that singlet oxygen is responsible for the cleavage activities of the water soluble quaternized tetra substituted peripherally phthalocyanines zinc(II) (6a) and copper (II) (7a) with irradiation. These results showed that both compounds may be potential anticancer drug for photodynamic therapy.

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