Photoinduced Superoxide Radical Anion and Singlet Oxygen Generation in the Presence of Novel Selenadiazoloquinolones (An EPR Study)

• Published in: Photochemistry and photobiology Vol. 87; no. 1; pp. 32 - 44
• Main Authors: Barbieriková, Zuzana, Bella, Maroš, Kučerák, Juraj, Milata, Viktor, Jantová, Soňa, Dvoranová, Dana, Veselá, Mária, Staško, Andrej, Brezová, Vlasta
• Format: Journal Article
• Language: English
• Published: Oxford, UK Blackwell Publishing Ltd 01-01-2011
• Subjects: Animals; Cancer; Cell Line, Tumor; Electron Spin Resonance Spectroscopy; Humans; Ions; Mice; Oxygen; Photobiology; Quinolones - chemistry; Singlet Oxygen - chemistry; Spectrophotometry, Ultraviolet; Spectrum analysis; Superoxides - chemistry; Ultraviolet Rays
• ISSN: 0031-8655; 1751-1097
• DOI: 10.1111/j.1751-1097.2010.00832.x

Novel 7‐substituted 6‐oxo‐6,9‐dihydro[1,2,5]selenadiazolo[3,4‐h]quinoline (SeQ(1–6)) and 8‐substituted 9‐oxo‐6,9‐dihydro[1,2,5]selenadiazolo[3,4‐f ]quinoline derivatives (SeQN(1–5)) with R7, R8 = H, COOC2H5, COOCH3, COOH, COCH3 or CN were synthesized and their spectral characteristics were obtained by UV/Vis spectroscopy. Ultraviolet A photoexcitation of the selenadiazoloquinolones in dimethylsulfoxide or acetonitrile resulted in the formation of paramagnetic species coupled with molecular oxygen activation generating the superoxide radical anion or singlet oxygen, evidenced by electron paramagnetic resonance spectroscopy. The cytotoxic/photocytotoxic impact of selenadiazoloquinolones on murine and human cancer cell lines was demonstrated using the derivative SeQ5 (with R7 = COCH3).