Synthesis of novel tetracationic phthalocyanines and investigation of their DNA-binding properties

Abstract

The synthesis of novel, tetracationic zinc ( 1Q ) and metal-free ( 2Q ) phthalocyanines (Pcs) bearing 4-((7-(trifluoromethyl)quinolin-4-yl)oxy) units on the periphery have been reported. The new compounds were characterized by using elemental analysis , 1 H NMR, UV–vis and FT-IR spectroscopy and mass spectrometry . The binding properties of both 1Q and 2Q to CT-DNA are investigated in water by absorption and fluorescence spectroscopy. The quenching effect of all quaternized phthalocyanines ( 1Q and 2Q ) on the fluorescence intensity of 4′,6-diamidino-2-phenylindoledihydrochloride (DAPI Gold)–DNA complex was determined. This study showed that the water-soluble quaternized zinc ( 1Q ) and metal-free phthalocyanines ( 2Q ) exhibit efficient DNA-binding activity. New tetracationic zinc ( 1Q ) and metal-free ( 2Q ) phthalocyanines (Pcs) bearing 4-((7-(trifluoromethyl)quinolin-4-yl)oxy) units on the periphery were prepared. Using absorption and fluorescence spectroscopy CT-DNA-binding properties of both 1Q and 2Q were also investigated. It is found that they can be bound to DNA efficiently. Thus they can be used for DNA photolysis of tumor cell. ► New quaternized zinc and metal-free phthalocyanines were synthesized and characterized. ► The interaction of the quaternized phthalocyanines ( 1Q and 2Q ) with CT-DNA were studied. ► The quenching effect of 1Q and 2Q on the fluorescence intensity of DAPI Gold–DNA complex was determined.