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

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).

[1]  M. Breza,et al.  Application of the Gould—Jacobs Reaction to 4-Amino-2,1,3-benzoselenadiazole. , 2011 .

[2]  J. Krutmann,et al.  Mechanisms of Phototoxic and Photoallergic Reactions , 2011 .

[3]  M. Breza,et al.  Application of the Gould–Jacobs reaction to 4-amino-2,1,3-benzoselenadiazole , 2010 .

[4]  S. Jantová,et al.  Effect of new synthetically prepared quinolone eth yl-1,4-dihydro- 8-nitro-4-oxoquinoline-3-carboxylate on human leukemia cell line HL-60 without/with presence of UVA irradiation , 2010 .

[5]  A. Boteva,et al.  The methods of synthesis, modification, and biological activity of 4-quinolones (review) , 2009 .

[6]  D. Hoban,et al.  In Vitro Activity of Nemonoxacin, a Novel Nonfluorinated Quinolone, against 2,440 Clinical Isolates , 2009, Antimicrobial Agents and Chemotherapy.

[7]  R. Kiss,et al.  7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: synthesis and in vitro biological evaluation as potential antitumor agents. , 2009, Bioorganic & medicinal chemistry.

[8]  H. Castro,et al.  Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives. , 2009, Bioorganic & medicinal chemistry.

[9]  S. Monti,et al.  Inter- and intramolecular photochemical reactions of fleroxacin. , 2009, Organic Letters.

[10]  S. Biskupic,et al.  Electron transfer: A primary step in the reactions of sodium hydrosulphide, an H2S/HS− donor , 2009, Free radical research.

[11]  Michal Zalibera,et al.  Thermal generation of stable spin trap adducts with super-hyperfine structure in their EPR spectra: An alternative EPR spin trapping assay for radical scavenging capacity determination in dimethylsulphoxide , 2009, Free radical research.

[12]  T. Rosenau,et al.  Spin trapping experiments with different carbamoyl-substituted EMPO derivatives. , 2008, Bioorganic & medicinal chemistry.

[13]  H. Cohen,et al.  Mechanism of the reaction of radicals with peroxides and dimethyl sulfoxide in aqueous solution. , 2008, Chemistry.

[14]  M. Wainwright,et al.  Photodynamic therapy: the development of new photosensitisers. , 2008, Anti-cancer agents in medicinal chemistry.

[15]  W. Kutner,et al.  In situ ESR spectroscopic evidence of the spin-trapped superoxide radical, O2−, electrochemically generated in DMSO at room temperature , 2008 .

[16]  P. Yogeeswari,et al.  Novel ofloxacin derivatives: synthesis, antimycobacterial and toxicological evaluation. , 2008, Bioorganic & medicinal chemistry letters.

[17]  N. Agrawal,et al.  Photosensitizing Potential of Ciprofloxacin at Ambient Level of UV Radiation , 2007, Photochemistry and photobiology.

[18]  N. Scheinfeld,et al.  Drug-induced photoallergic and phototoxic reactions , 2007, Expert opinion on drug safety.

[19]  A. Mercier,et al.  Combined ESR and thermodynamic studies of the superoxide adduct of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO): hindered rotation around the O-O bond evidenced by two-dimensional simulation of temperature-dependent spectra. , 2007, The journal of physical chemistry. A.

[20]  L. Cipak,et al.  Photochemical and phototoxic activity of berberine on murine fibroblast NIH-3T3 and Ehrlich ascites carcinoma cells. , 2006, Journal of photochemistry and photobiology. B, Biology.

[21]  V. Machado,et al.  Solute-solvent and solvent-solvent interactions in the preferential solvation of 4-[4-(dimethylamino)styryl]-1-methylpyridinium iodide in 24 binary solvent mixtures. , 2006, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[22]  Volodymyr G Bdzhola,et al.  Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2. , 2006, Journal of medicinal chemistry.

[23]  T. Rosenau,et al.  Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives. , 2006, Bioorganic & medicinal chemistry.

[24]  Jinjie Jiang,et al.  Characterization of the high-resolution ESR spectra of superoxide radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO). Analysis of conformational exchange , 2005, Free radical research.

[25]  M. Hidalgo,et al.  Induced and Photoinduced DNA Damage by Quinolones: Ciprofloxacin, Ofloxacin and Nalidixic Acid Determined by Comet Assay¶ , 2005 .

[26]  D. Dvoranová,et al.  Reactive oxygen species produced upon photoexcitation of sunscreens containing titanium dioxide (an EPR study). , 2005, Journal of photochemistry and photobiology. B, Biology.

[27]  Hans Jürgen Ahr,et al.  Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods. , 2005, Journal of photochemistry and photobiology. B, Biology.

[28]  T. Rosenau,et al.  Spin adduct formation from lipophilic EMPO-derived spin traps with various oxygen- and carbon-centered radicals. , 2005, Biochemical pharmacology.

[29]  Steven Yue Qian,et al.  A novel protocol to identify and quantify all spin trapped free radicals from in vitro/in vivo interaction of HO(.-) and DMSO: LC/ESR, LC/MS, and dual spin trapping combinations. , 2005, Free radical biology & medicine.

[30]  J. N. Ribeiro,et al.  Involvement of mitochondria in apoptosis of cancer cells induced by photodynamic therapy , 2004 .

[31]  R. Murugesan,et al.  Photosensitisation and photoinduced DNA cleavage by four naturally occurring anthraquinones , 2004 .

[32]  Y. Nakata,et al.  New Findings on the Structure-Phototoxicity Relationship and Photostability of Fluoroquinolones with Various Substituents at Position 1 , 2004, Antimicrobial Agents and Chemotherapy.

[33]  M. Mphahlele,et al.  Tautomeric 2-arylquinolin-4(1H)-one derivatives- spectroscopic, X-ray and quantum chemical structural studies , 2004 .

[34]  S. Braslavsky,et al.  Chemical actinometry (IUPAC Technical Report) , 2004 .

[35]  R. Mason,et al.  Characterization of the High Resolution ESR Spectra of the Methoxyl Radical Adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) , 2003, Free radical research.

[36]  A. MacGowan,et al.  Development of the quinolones. , 2003, The Journal of antimicrobial chemotherapy.

[37]  A. Catalfo,et al.  Photochemical properties of ofloxacin involved in oxidative DNA damage: a comparison with rufloxacin. , 2003, Chemical research in toxicology.

[38]  S. Biskupic,et al.  EPR study of photoinduced reduction of nitroso compounds in titanium dioxide suspensions , 2003 .

[39]  E. Oliveros,et al.  Effect of the Media on the Quantum Yield of Singlet Oxygen (O2(1Δg)) Production by 9H-Fluoren-9-one: Solvents and Solvent Mixtures , 2003 .

[40]  C. Hahn,et al.  The simultaneous voltammetric determination and detection of oxygen and carbon dioxide A study of the kinetics of the reaction between superoxide and carbon dioxide in non-aqueous media using membrane-free gold disc microelectrodes , 2003 .

[41]  P. Tordo,et al.  5-Diisopropoxyphosphoryl-5-methyl-1-pyrroline N-oxide, DIPPMPO, a crystalline analog of the nitrone DEPMPO: synthesis and spin trapping properties , 2002 .

[42]  E. Oliveros,et al.  Degradation of nitroaromatic compounds by the UV–H_2O_2 process using polychromatic radiation sources , 2002, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[43]  K. Stolze,et al.  Spin Adducts of Superoxide, Alkoxyl, and Lipid-Derived Radicals with EMPO and Its Derivatives , 2002, Biological chemistry.

[44]  R. Stahlmann.  Clinical toxicological aspects of fluoroquinolones. , 2002, Toxicology letters.

[45]  J. Cadet,et al.  Analysis of Fluoroquinolone-mediated Photosensitization of 2′-Deoxyguanosine, Calf Thymus and Cellular DNA: Determination of Type-I, Type-II and Triplet–Triplet Energy Transfer Mechanism Contribution¶ , 2001, Photochemistry and photobiology.

[46]  R. Mason,et al.  Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals: reassignment to alkoxyl radical adducts. , 2001, Free radical biology & medicine.

[47]  A. Mercier,et al.  2-ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide: evaluation of the spin trapping properties. , 2000, Free radical biology & medicine.

[48]  A. Al-majed,et al.  Methods of analysis of 4-quinolone antibacterials. , 1999, Talanta.

[49]  R. Mason,et al.  Reassignment of organic peroxyl radical adducts. , 1999, Free radical biology & medicine.

[50]  R. Murugesan,et al.  Photodynamic action of some naturally occurring quinones: formation of reactive oxygen species , 1999 .

[51]  V. Padmavathi,et al.  Selena and Thiadiazole Fused Heterocycles. , 1999 .

[52]  E. Fasani,et al.  Structure and Medium‐Dependent Photodecomposition of Fluoroquinolone Antibiotics , 1998, Photochemistry and photobiology.

[53]  L. Martínez,et al.  Photocleavage of DNA by the fluoroquinolone antibacterials. , 1998, Journal of photochemistry and photobiology. B, Biology.

[54]  M. Wainwright,et al.  Photodynamic antimicrobial chemotherapy (PACT). , 1998, Journal of Antimicrobial Chemotherapy.

[55]  L. Martínez,et al.  Fluoroquinolone Antimicrobials: Singlet Oxygen, Superoxide and Phototoxicity , 1998, Photochemistry and photobiology.

[56]  J. E. Rosen.  Proposed mechanism for the photodynamic generation of 8-oxo-7,8-dihydro-2'-deoxyguanosine produced in cultured cells by exposure to lomefloxacin. , 1997, Mutation research.

[57]  G. Williams,et al.  Quinolone Antibiotic Photodynamic Production of 8‐Oxo‐7,8‐dihydro‐2‘‐deoxyguanosine in Cultured Liver Epithelial Cells , 1997, Photochemistry and photobiology.

[58]  L. Martínez,et al.  Photogeneration of Fluoride by the Fluoroquinolone Antimicrobial Agents Lomefloxacin and Fleroxacin , 1997, Photochemistry and photobiology.

[59]  P. Tordo,et al.  Use of new β-phosphorylated nitrones for the spin trapping of free radicals , 1996 .

[60]  B. R. Misra,et al.  The specificity and product of quenching singlet oxygen by 2,2,6,6-tetramethylpiperidine. , 1995, Biochemistry and molecular biology international.

[61]  Jiali Gao,et al.  POLARIZATION EFFECTS ON THE TAUTOMERIC EQUILIBRIA OF 2- AND 4-HYDROXYPYRIDINE IN AQUEOUS AND ORGANIC SOLUTION , 1994 .

[62]  S. Pietri,et al.  5-Diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO): a new phosphorylated nitrone for the efficient In Vitro and In Vivo spin trapping of oxygen-centred radicals , 1994 .

[63]  H. Ohya-Nishiguchi,et al.  Detection of Superoxide Ions from Photoexcited Semiconductors in Non-Aqueous Solvents Using the ESR Spin-Trapping Technique. , 1993 .

[64]  J. Elguero,et al.  Tautomerism and Acidity in 4-Quinolone-3-carboxylic Acid Derivatives. , 1992 .

[65]  N. Turro,et al.  Solvent and deuterium isotope effects on the lifetime of singlet oxygen determined by direct emission spectroscopy at 1.27 μm , 1982 .