Phthalocyanines (Pcs) are aromatic macrocyclic compounds with 18 π electron systems and have high chemical, physical, and thermal stability owing to high electron transfer abilities. Due to their properties, Pc derivatives can be implemented in medicinal and pharmaceutical product development with the final aims of commercial and industrial implementations. So, they can be used in many biological applications such as medical applications, photodynamic therapy, antifungal, antioxidant and antibacterial agents. For suitable applications, the design of phthalocyanines with the desired properties can be achieved by diversifying the central metal atoms and side groups of the Pc molecules.
Recently, Kocak group has focused on the synthesis and characterization of fluorine-bearing compounds at different positions of the Pc ring and has investigated the potential of their use in different areas including nonlinear optics, biology, and electrochemistry. There are limited number in the literature reporting the synthesis and characterization of unsymmetric phthalocyanines owing to the difficulty of the separation procedure and low yield. Hence, the study of their efficiency and properties (especially biological features) has been limited. This study aims to extend the knowledge on the biological performance of unsymmetrically substituted Pcs and to compare the obtained results with those of the symmetrically substituted Pcs. For this purpose, unsymmetrically substituted ZnPc derivative containing 4-(trifluoromethoxy) thiophenol groups and 4-[(4-nitrophenyl) ethynyl] phthalonitrile group was synthesized in this study. Additionally, two new symmetrically octasubstituted cobalt phthalocyanine CoPc and ZnPc derivatives carrying 4-(trifluoromethoxy)thiophenol groups at their peripheral positions were synthesized. Various biological abilities such as antioxidant, antimicrobial,cell viability, and biofilm inhibition were investigated. The effects of the central metal ion in synthesized symmetric Pc derivatives and substitution change in synthesized symmetric and unsymmetric ZnPc derivatives on the biological properties of molecules were compared.
Pcs demonstrated effective DNA cleavage and antimicrobial activities. Also, test compounds exhibited good biofilm inhibition activity. The good biological activities results showed that the newly synthesized phthalocyanine compounds promise to use them in medical industries after several toxicological test systems.
The compounds in the aforementioned study were synthesized by Dr. Hande R. Pekbelgin Karaoğlu and Assoc. Prof. Dr. Özgül Sağlam under the supervision of Prof. Dr. Makbule Burkut Koçak and their biological properties were investigated by Prof. Dr. Sadin Özdemir et al. The study was published in Dalton Transtion, one of the most distinguished journals on inorganic chemistry, which has an extremely high impact factor, and was featured on the cover of its 50th issue.