Synthesis of novel DNA-interacting phthalocyanines

The new copper hexamethyleneimino-ethoxy substituted phthalocyanine (pc) (2) and its quaternized derivative (2Q) were synthesized. The interaction of quaternized copper (2Q), quaternized cobalt (3Q) and zinc (4Q) phthalocyanines (pcs) with calf thymus (CT) DNA was investigated by UV/Vis spectrophotometric methods and gel electrophoresis. With the addition of pcs, the change in the thermal denaturation profile of DNA was observed. The results indicated that these molecules exhibit efficient DNA binding activity. Generation of singlet oxygen by 2 and 2Q and photocleavage of CT-DNA were determined. All the experimental data proved that these water soluble pcs can act as active components in the photocleavage of DNA.

New hexamethyleneimino-ethoxy substituted copper phthalocyanine and its water soluble quaternized derivative were prepared. Together with previously synthesized quaternized cobalt and zinc derivatives, their interaction with CT-DNA and abilities to generate singlet oxygen were discussed. Furthermore, the photocleavage of supercoiled DNA was proved.Figure optionsDownload as PowerPoint slideHighlights
► Singlet oxygen generation of copper phthalocyanines were tested.
► The binding of novel phthalocyanines to CT-DNA were proved.
► Photocleavage of supercoiled DNA by pcs 2Q, 3Q and 4Q were tested.