Summary:
In the present research work, the design and synthesis of chemiluminescent, photoactive, mitotropic organic compounds based on acridine esters are described. N-methylated and N-alkylated acridine ester derivatives with different structural characteristics were synthesized and studied. Synthetic routes are based on the esterification reaction of acridine acid with suitable phenols, as well as on the N-methylation or N-alkylation reaction, respectively. An appropriate methodology was then developed for the preparation of acridine esters bearing mitotropic phosphonate cations. Characteristic of these esters is the chemiluminescence they show under suitable oxidation conditions, and, as such, have been widely used in analytical and biochemical applications. The aim of all final derivatives is the investigation of chemiluminescence and their possible photochemical action, in the developing field of photodynamic and targeted therapy, against cancerous tumors, including those of the brain. All intermediate and final products were characterized using NMR (1H, 13C, 19F και 31P NMR) and MS spectroscopy (ESI-MS). These derivatives are expected to be chemiluminescent compounds. This property, in combination with their other structural characteristics, is expected to lead to their utilization in biological applications.
Keywords:
acridinium esters, dioxetane, phosphonium cations, chemiluminescence
