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

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, 1H NMR, 19F 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.Figure optionsDownload as PowerPoint slideHighlights
► 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.