Synthesis of pyridine substituted phthalocyanines and their DNA binding properties

Phthalocyanines, being tetrapyrrole derivatives, constitute an important class of compounds both in basic researches and in applied sciences. Adding desired functional groups to the periphery of phthalocyanine rings changes its optical, electronic and catalytic properties and enables them to be used in different areas. Owing to these properties, phthalocyanines have been used in dyestuffs, photochromic and electrochromic materials, liquid crystals, catalysts, chemical sensors, gas sensors in the form of Langmuir-Blodgett films, and non-linear optical materials. Adding water-soluble groups to phthalocyanines as functional groups has also enabled them to be researched in the therapy of cancer. Today, phthalocyanines are being used as second-generation photosensitizers. Compared with the first-generation photosensitizers such as hematoporphyrin derivative, metallophthalocyanines have a much higher extinction coefficient of the Q‑band near 680 nm, which means that they are efficiently excited directly through tissue, whereas the introduction of hydrophilic groups into substituted phthalocyanine derivatives has been performed in order to achieve solubility in aqueous media. Phthalocyanines having water soluble groups have a strong influence on the bioavailability and in vivo distribution. While the ionic groups provide binding of phthalocyanines to DNA and proteins (e.g. BSA). Within the scope of this thesis, suitable substituents were attached to the phthalocyanine rings and metallophthalocyanines were synthesized by incorporating different metal ions. For this purpose, iodophthalonitrile was synthesized as a first step and tetraiodozinc phthalocyanine was synthesized with zinc acetate as the metal ion in a suitable solvent. Under typical Sonogashira reaction conditions, the cross-coupling reaction between an excess of 2-ethynyl pyridine and tetraiodo-metallophthalocyanines in triethylamine with copper(I)iodide (CuI) and bis(triphenylphosphine)palladium(II)chloride [Pd(PPh3)2Cl2] as catalysts at room temperature under nitrogen atmosphere produced 2,9(10),16(17),23(24)-tetra-(3-pyridylethynyl) phthalocyaninato zinc(II). For the synthesis of water-soluble phthalocyanine derivatives, pyridine groups were introduced into the reaction to synthesize quaternized derivatives. The phthalocyanines were reacted with excess amount of dimethyl sulfate. The same method was applied to obtain Co(II) phthalocyanine and its quaternary derivative. The new compounds were characterized 1H-NMR, FTIR and UV-Vis techniques. The aggregation and binding to DNA and BSA properties were investigated.