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, H-1 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. (C) 2012 Elsevier Ltd. All rights reserved.