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

Authors

  • Zuzana Barbieriková,

    1. Faculty of Chemical and Food Technology, Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovak Republic
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  • Maroš Bella,

    1. Faculty of Chemical and Food Technology, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Bratislava, Slovak Republic
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  • Juraj Kučerák,

    1. Faculty of Chemical and Food Technology, Institute of Biochemistry, Nutrition and Health Protection, Slovak University of Technology, Bratislava, Slovak Republic
    2. Institute of Neuroimmunology, Slovak Academy of Sciences, Bratislava, Slovak Republic
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  • Viktor Milata,

    1. Faculty of Chemical and Food Technology, Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Bratislava, Slovak Republic
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  • Soňa Jantová,

    1. Faculty of Chemical and Food Technology, Institute of Biochemistry, Nutrition and Health Protection, Slovak University of Technology, Bratislava, Slovak Republic
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  • Dana Dvoranová,

    1. Faculty of Chemical and Food Technology, Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovak Republic
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  • Mária Veselá,

    1. Faculty of Chemistry, Institute of Food Science and Biotechnology, Brno University of Technology, Brno, Czech Republic
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  • Andrej Staško,

    1. Faculty of Chemical and Food Technology, Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovak Republic
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  • Vlasta Brezová

    Corresponding author
    1. Faculty of Chemical and Food Technology, Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Bratislava, Slovak Republic
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Corresponding author email: vlasta.brezova@stuba.sk (Vlasta Brezová)

Abstract

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).

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