Synthesis of tetra(trimethylammonio)phthalocyanato zinc tetraiodide, [ZnPc(NMe3)4]I4, and a spectrometric investigation of its interaction with calf thymus DNA

Abstract

The phthalocyanine salt [ ZnPc(NMe3)4]I4was synthesized from 4-nitrophthalonitrile using a three-step procedure. The interaction of [ ZnPc(NMe3)4]4+with calf thymus DNA (CT DNA) has been investigated by UV-vis and fluorescence spectrometric methods. [ ZnPc(NMe3)4]4+exists in a non-monomeric form, proposed to be a dimer, in phosphate buffer solution (pH 6.82). Spectral changes show that in the presence of high concentrations of CT DNA added to the solution, [ ZnPc(NMe3)4]4+is bound in a monomeric state with evidence suggesting it is located in a DNA groove. At lower concentrations of DNA there is evidence of stacking of non-monomeric [ ZnPc(NMe3)4]4+onto the DNA. Two intrinsic binding constants for the interaction of [ ZnPc(NMe3)4]4+with CT DNA, 1.33 × 105and 2.56 × 104M-1have been obtained. Electrostatic binding is shown to play an important role in the interaction of [ ZnPc(NMe3)4]4+with nucleic acids.