Synthesis and biological activity of novel phthalocyanines with dietheroxy and nitroimidazolylethoxy moieties


Nejat Düzgüneş: 0000-0001-6159-1391


Biomedical Sciences

Document Type

Conference Presentation

Conference Title

15th JCF-Fruhjahrssymposium


Berlin, Germany

Conference Dates

March 6-9, 2013

Date of Presentation



Phthalocyanines (Pcs) are aromatic macrocyclic compounds consisting of four isoindole fragments linked together with azomethine groups. These synthetic analogues of natural porphyrinoids are known to possess wide applications in dyes industry, In materials chemistry as sensors, molecular semiconductors and non-linear optical materials, and as photosensitizers in photodynamic therapy. Medical applications of phthalocyanines impose good solubility in water and increased accumulation in pathologic tissues. The structure of Pcs may be modified by introducing substituents at their peripheral and non-peripheral positions, as well as various metal ions into the central cavity of a macrocycle. Good solubility in water can be reached by introducing polyetheric substituents in non-peripheral positions. Increased accumulation in hypoxic tissues such as can tissues can be reached by incorporating nitroimidazole moieties to the structure. New compounds were synthesized according to the procedure shown on Figure 1 [see PDF]. Newly synthesized phthalocyanines Pc-1, Pc-2, Pc-3, Pc-4 as well as the precursor dinitriles 1 and 2 were fully characterized by NMR, UV-Vis, MS, HPLC. Additionally, new dinitryles were characterized by combustion analysis and crystallographic data. New phthalocyanines were tested for photodynamic activity against human oral squamous carcinoma cells HSC-3. The best activity was revealed by compound Pc-3 possessing two types of substituents - dietheroxy and nitroimidazolylethoxy. Pc-3 showed phototoxicity at the level of IC50 0.10 μM. Zinc compound Pc-2 was three times more active than the magnesium Pc-1 and seems to be a promising compound for further research. This study was supported by the National Science Centre under Grant No. N401067238.