Tetracationic fluorinated zinc(ii)phthalocyanine: Synthesis, characterization and DNA-binding properties

Abstract

Selective replacement of the p -fluorine atom of 4-(2′,3′,4′,5′,6′-pentafluorobenzyloxy) phthalonitrile with N,N-dimethylaminoetanethiol gave 4-[2′,3′,5′,6′-tetrafluoro-4′-(2-dimethylaminoetanethio)benzyloxy]phthalonitrile. A peripherally tetra-substituted zinc(II) phthalocyanine was achieved by tetramerization of the new perfluorobenzyloxyphthalonitrile in the presence of zinc acetate. The zinc derivative was quaternized with methyl iodide to afford a water-soluble product. The new compounds were characterized by using elemental analyses, 1 H NMR, 19 F NMR, UV–vis and FT-IR spectroscopy and mass spectrometry . The interaction between the quaternized zinc phthalocyanine and calf thymus DNA was investigated in tris buffer (pH 7.4) by absorption and fluorescence spectroscopy. Upon addition of the quaternized zinc phthalocyanine, a change in the thermal denaturation profile of DNA was observed. New organo-soluble and water soluble zinc(II)phthalocyanines bearing functionalized polyfluorinated groups were prepared. Using absorption and fluorescence spectroscopy ct-DNA binding properties of tetracationic ZnPc were also investigated and the change in the melting point of ct-DNA was determined with thermal denaturation profiles. ► New fluorinated zinc phthalocyanines were prepared and characterized. ► The zinc derivative was converted into the water-soluble quaternized product. ► The interaction of the quaternized phthalocyanine with calf thymus DNA was studied. ► The change in the melting point of DNA was determined.