Research Information System
INTERNATIONAL CONGRESS ON SCIENTIFIC RESEARCH-VIII , Ankara, Turkey, 9 - 11 June 2023, pp.123-124
Photodynamic inactivation (PDI) is an effective method in the fight against microorganisms and is an alternative treatment method that can be used in the treatment of microbial infections. Porphyrin, phthalocyanines, chlorines, texafirines, and phenothiazines are some molecules used in this method. The basis of this method is; a photosensitive molecule relies on the presence of visible light and molecular oxygen. These parameters enable the formation of reactive oxygen species responsible for the realization of the PDI process. These reactive oxygen species react with various macromolecules of microbial cells and cause cellular oxidative damage depending on the intracellular location of the photosensitive molecule and ultimately leading to cell death. Within the scope of this study, the synthesis of cationic porphyrin derivatives with very good results in photodynamic inactivation method was studied. The functional groups added to the porphyrin molecule add many different properties such as increasing the efficiency of PDI, improving the intracellular population, preventing aggregation, and increasing solubility. In this study, coumarin derivatives, an agent with known anticancer activity, were used as a functional group. These coumarin derivatives were derivatized by different intermediate reactions and combined with the porphyrin molecule. Synthesis of porphyrin was carried out using the Adler-Longo Method. According to this method, target porphyrin was synthesized by mixing pyrrole molecule and 4- pyridinecarbaldehyde in propionic acid at 140 °C under reflux. Purification was carried out by neutralization with weak base, precipitation in methanol, filtration and extraction in dichloromethane solvent under Soxhlet, respectively. Finally, pure porphyrin was obtained by chromatographic purification over dichloromethane. For the cationic part of the molecule, two different coumarin molecules containing hydroxyl groups were synthesized by Pechman condensation. Next, the hydroxyl group of coumarin molecules was treated with alkyl hologen. Finally, the obtained coumarin derivatives reacted with porphyrin under basic conditions and new brown-purple colored porphyrin derivatives with cationic structure were obtained.
Keywords: PDI, Porphyrin, Coumarin