The synthesis, characterization, DNA binding features and investigation of in vitro properties of new morpholine containing zinc (II) phthalocyanines

Abstract

The novel peripheral and non–peripheral tetra triazole linked morpholine substituted phthalocyanines were synthesized via multistep reactions. The target zinc (II) phthalocyanines were obtained by the cyclotetramerization reaction of precursor nitriles containing triazole linked morpholine and zinc(II)acetate. And then, the synthesized zinc phthalocyanine compounds were made water–soluble with methyl iodide in chloroform. These newly synthesized phthalonitriles and related phthalocyanines have been characterized by a combination of ¹H and ¹³C NMR, FT–IR, UV–vis, elemental analysis and MS spectral data. The DNA binding activities of Q–np–ZnPc and Q–p–ZnPc were assessed by UV–vis absorption titration, thermal denaturing and viscosity experiments, and the complexes were detected to bind to DNA via an intercalative binding mechanism. Besides, the antiproliferative effects of water–soluble zinc (II) phthalocyanines (Q–p–ZnPc and Q–np–ZnPc) were investigated in lung cancer cell lines. Our findings show that Q–p–ZnPc and Q–np–ZnPc significantly inhibit the cell proliferation of the lung cancer cell lines.