Synthesis of unsymmetrical cationic phthalocyanines for photodynamic therapy

Charles University, Faculty of Pharmacy in Hradec Králové Department Department of Pharmaceutical Chemistry and Drug Control Candidate Filip Kostelanský Supervisor Doc. PharmDr. Petr Zimčík, Ph.D. Title of Thesis Synthesis of Unsymmetrical Cationic Phthalocyanines for Photodynamic Therapy The photodynamic therapy is a curative method of cancerous and non-cancerous diseases. It uses light, oxygen and photosensitizer to destroy the cancer cells. Photosensitizer absorbs energy of light and produces singlet oxygen. Singlet oxygen attacks cellular structures like cellular membrane, lysosomes, mitochondria, etc. causing thus damage leading to cell death. Previous studies revealed that zinc phthalocyanine with methylated 2,6-bis[(1H-imidazol-1-yl)methyl]-4-methylphenoxy substituents had excellent photodynamic activity against HeLa cells and low toxicity. That is why we decided to synthesize a series of similar compounds bearing this substituent but with rather amphiphilic character. They bear interesting spatial features to be potentially incorporated into lipid bilayer or a double stranded DNA. The synthesis started by condensation of 2,6- bis(hydroxymethyl)-4-methylphenol and imidazole to obtain 2,6-bis[(imidazol-1- yl)methyl]-4-methylphenol. In the following reaction, this phenol was subjected to..