Spectroscopic characterization, photoinduced processes and cytotoxic properties of substituted N-ethyl selenadiazoloquinolones
7‐R‐9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinolines (R = H, COOC2H5, COOCH3, COOH and COCH3, E1h, E2h, E3h, E4h, E5h) and 6‐ethyl‐6,9‐dihydro‐9‐oxo‐[1,2,5]selenadiazolo[3,4‐f]quinoline (E1f) were characterized by UV/vis, FT‐IR and fluorescence spectroscopy. The electronic absorption...
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Published in | Journal of physical organic chemistry Vol. 26; no. 7; pp. 565 - 574 |
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Main Authors | , , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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Bognor Regis
Blackwell Publishing Ltd
01.07.2013
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Abstract | 7‐R‐9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinolines (R = H, COOC2H5, COOCH3, COOH and COCH3, E1h, E2h, E3h, E4h, E5h) and 6‐ethyl‐6,9‐dihydro‐9‐oxo‐[1,2,5]selenadiazolo[3,4‐f]quinoline (E1f) were characterized by UV/vis, FT‐IR and fluorescence spectroscopy. The electronic absorption spectra of the derivatives E1h, E2h, E3h and E5h in the aprotic solvents dimethylsulfoxide (DMSO) and acetonitrile (ACN) reveal low‐energy absorption maxima with λmax > 400 > nm, shifted hypsochromically in water. In DMSO, N‐ethyl selenadiazoloquinolones behave as strong fluorescent agents (λem ≥ 550 nm) with the exception of the carboxylic acid derivative E4h which shows only poor emission. Photoinduced reactions of N‐ethyl selenadiazoloquinolones were investigated by means of electron paramagnetic resonance (EPR) spectroscopy. Photoexcitation of N‐ethyl selenadiazoloquinolones in aerated DMSO with either 385 nm or 400 nm wavelengths, monitored by EPR spin trapping technique, results in the generation of superoxide radical anions; under an inert atmosphere, the generation of methyl radicals originating from the solvent predominates. Upon exposure at either 365 nm, 385 nm or 400 nm, aerated ACN solutions of selenadiazoloquinolones in the presence of sterically hindered amines produce nitroxide radicals via a reaction with photogenerated singlet oxygen. The 7‐substituted derivatives of 9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinoline behave as photosensitizers activating molecular oxygen upon photoexcitation and possess the sufficient photochemical stability under the given experimental conditions. The cytotoxic effects of non‐photoactivated and UVA photoactivated N‐ethyl substituted selenadiazoloquinolones on cancer (human HeLa and murine L1210) and non‐cancer (NIH‐3T3) cell lines were monitored by the MTT test. The derivative E2h demonstrates the highest cytotoxic/photocytotoxic activity on the neoplastic cell lines. Copyright © 2013 John Wiley & Sons, Ltd.
7‐R‐9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinolines and 6‐ethyl‐6,9‐dihydro‐9‐oxo‐[1,2,5]selenadiazolo[3,4‐f]quinoline were synthesized and characterized by UV/vis, FT‐IR and fluorescence spectroscopy; the generation of superoxide radical anions and singlet oxygen was monitored by electron paramagnetic resonance spin trapping technique and sterically hindered amine oxidation. |
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AbstractList | 7-R-9-ethyl-6,9-dihydro-6-oxo-[1,2,5]selenadiazolo[3,4-h]quinolines (R=H, COOC2H5, COOCH3, COOH and COCH3, E1h, E2h, E3h, E4h, E5h) and 6-ethyl-6,9-dihydro-9-oxo-[1,2,5]selenadiazolo[3,4-f]quinoline (E1f) were characterized by UV/vis, FT-IR and fluorescence spectroscopy. The electronic absorption spectra of the derivatives E1h, E2h, E3h and E5h in the aprotic solvents dimethylsulfoxide (DMSO) and acetonitrile (ACN) reveal low-energy absorption maxima with λmax>400> nm, shifted hypsochromically in water. In DMSO, N-ethyl selenadiazoloquinolones behave as strong fluorescent agents (λem ≥ 550 nm) with the exception of the carboxylic acid derivative E4h which shows only poor emission. Photoinduced reactions of N-ethyl selenadiazoloquinolones were investigated by means of electron paramagnetic resonance (EPR) spectroscopy. Photoexcitation of N-ethyl selenadiazoloquinolones in aerated DMSO with either 385 nm or 400 nm wavelengths, monitored by EPR spin trapping technique, results in the generation of superoxide radical anions; under an inert atmosphere, the generation of methyl radicals originating from the solvent predominates. Upon exposure at either 365 nm, 385 nm or 400 nm, aerated ACN solutions of selenadiazoloquinolones in the presence of sterically hindered amines produce nitroxide radicals via a reaction with photogenerated singlet oxygen. The 7-substituted derivatives of 9-ethyl-6,9-dihydro-6-oxo-[1,2,5]selenadiazolo[3,4-h]quinoline behave as photosensitizers activating molecular oxygen upon photoexcitation and possess the sufficient photochemical stability under the given experimental conditions. The cytotoxic effects of non-photoactivated and UVA photoactivated N-ethyl substituted selenadiazoloquinolones on cancer (human HeLa and murine L1210) and non-cancer (NIH-3T3) cell lines were monitored by the MTT test. The derivative E2h demonstrates the highest cytotoxic/photocytotoxic activity on the neoplastic cell lines. Copyright © 2013 John Wiley & Sons, Ltd. Dedicated to Professor Andrej Stasko on the occasion of his 75th birthday [PUBLICATION ABSTRACT] 7‐R‐9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinolines (R = H, COOC2H5, COOCH3, COOH and COCH3, E1h, E2h, E3h, E4h, E5h) and 6‐ethyl‐6,9‐dihydro‐9‐oxo‐[1,2,5]selenadiazolo[3,4‐f]quinoline (E1f) were characterized by UV/vis, FT‐IR and fluorescence spectroscopy. The electronic absorption spectra of the derivatives E1h, E2h, E3h and E5h in the aprotic solvents dimethylsulfoxide (DMSO) and acetonitrile (ACN) reveal low‐energy absorption maxima with λmax > 400 > nm, shifted hypsochromically in water. In DMSO, N‐ethyl selenadiazoloquinolones behave as strong fluorescent agents (λem ≥ 550 nm) with the exception of the carboxylic acid derivative E4h which shows only poor emission. Photoinduced reactions of N‐ethyl selenadiazoloquinolones were investigated by means of electron paramagnetic resonance (EPR) spectroscopy. Photoexcitation of N‐ethyl selenadiazoloquinolones in aerated DMSO with either 385 nm or 400 nm wavelengths, monitored by EPR spin trapping technique, results in the generation of superoxide radical anions; under an inert atmosphere, the generation of methyl radicals originating from the solvent predominates. Upon exposure at either 365 nm, 385 nm or 400 nm, aerated ACN solutions of selenadiazoloquinolones in the presence of sterically hindered amines produce nitroxide radicals via a reaction with photogenerated singlet oxygen. The 7‐substituted derivatives of 9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinoline behave as photosensitizers activating molecular oxygen upon photoexcitation and possess the sufficient photochemical stability under the given experimental conditions. The cytotoxic effects of non‐photoactivated and UVA photoactivated N‐ethyl substituted selenadiazoloquinolones on cancer (human HeLa and murine L1210) and non‐cancer (NIH‐3T3) cell lines were monitored by the MTT test. The derivative E2h demonstrates the highest cytotoxic/photocytotoxic activity on the neoplastic cell lines. Copyright © 2013 John Wiley & Sons, Ltd. 7‐R‐9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinolines and 6‐ethyl‐6,9‐dihydro‐9‐oxo‐[1,2,5]selenadiazolo[3,4‐f]quinoline were synthesized and characterized by UV/vis, FT‐IR and fluorescence spectroscopy; the generation of superoxide radical anions and singlet oxygen was monitored by electron paramagnetic resonance spin trapping technique and sterically hindered amine oxidation. |
Author | Sekeráková, Ľudmila Heizer, Tomáš Milata, Viktor Jantová, Soňa Brezová, Vlasta Lietava, Jozef Hudec, Roman Dvoranová, Dana Topoľská, Dominika Barbieriková, Zuzana Bella, Maroš Bobeničová, Miroslava Czímerová, Adriana Sádecká, Jana |
Author_xml | – sequence: 1 givenname: Zuzana surname: Barbieriková fullname: Barbieriková, Zuzana email: Correspondence to: Z. Barbieriková, Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovak Republic., zuzana.barbierikova@stuba.sk organization: Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 2 givenname: Maroš surname: Bella fullname: Bella, Maroš organization: Slovak Academy of Sciences, Institute of Chemistry, Dúbravská cesta 9, SK-845 38, Bratislava, Slovak Republic – sequence: 3 givenname: Ľudmila surname: Sekeráková fullname: Sekeráková, Ľudmila organization: Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 4 givenname: Jozef surname: Lietava fullname: Lietava, Jozef organization: Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 5 givenname: Miroslava surname: Bobeničová fullname: Bobeničová, Miroslava organization: Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 6 givenname: Dana surname: Dvoranová fullname: Dvoranová, Dana organization: Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 7 givenname: Viktor surname: Milata fullname: Milata, Viktor organization: Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 8 givenname: Jana surname: Sádecká fullname: Sádecká, Jana organization: Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 9 givenname: Dominika surname: Topoľská fullname: Topoľská, Dominika organization: Institute of Biochemistry, Nutrition and Health Protection, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 10 givenname: Tomáš surname: Heizer fullname: Heizer, Tomáš organization: Institute of Biochemistry, Nutrition and Health Protection, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 11 givenname: Roman surname: Hudec fullname: Hudec, Roman organization: Institute of Biochemistry, Nutrition and Health Protection, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 12 givenname: Adriana surname: Czímerová fullname: Czímerová, Adriana organization: Slovak Academy of Sciences, Institute of Inorganic Chemistry, Dúbravská cesta 9, SK-845 36, Bratislava, Slovak Republic – sequence: 13 givenname: Soňa surname: Jantová fullname: Jantová, Soňa organization: Institute of Biochemistry, Nutrition and Health Protection, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic – sequence: 14 givenname: Vlasta surname: Brezová fullname: Brezová, Vlasta organization: Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic |
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Snippet | 7‐R‐9‐ethyl‐6,9‐dihydro‐6‐oxo‐[1,2,5]selenadiazolo[3,4‐h]quinolines (R = H, COOC2H5, COOCH3, COOH and COCH3, E1h, E2h, E3h, E4h, E5h) and... 7-R-9-ethyl-6,9-dihydro-6-oxo-[1,2,5]selenadiazolo[3,4-h]quinolines (R=H, COOC2H5, COOCH3, COOH and COCH3, E1h, E2h, E3h, E4h, E5h) and... |
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SubjectTerms | Cytotoxicity EPR spectroscopy neoplastic cell lines Oxygen quinolones reactive oxygen species selenium-containing heterocycles Spectrum analysis spin trapping |
Title | Spectroscopic characterization, photoinduced processes and cytotoxic properties of substituted N-ethyl selenadiazoloquinolones |
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