Photoinduced superoxide radical anion and singlet oxygen generation in the presence of novel selenadiazoloquinolones (An EPR study)

Photochemistry and Photobiology

Volumn 87, Issue 1, 2011, Pages 32-44

  Barbieriková, Zuzana ^a   Bella, Maroš ^a   Kučerák, Juraj ^a,b   Milata, Viktor ^a   Jantová, Soňa ^a   Dvoranová, Dana ^a   Veselá, Mária ^c   Staško, Andrej ^a   Brezová, Vlasta ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b INSTITUTE OF NEUROIMMUNOLOGY   (Slovakia)

^c BRNO UNIVERSITY OF TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLONE DERIVATIVE; SINGLET OXYGEN; SUPEROXIDE;

ANIMAL; ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; HUMAN; MOUSE; TUMOR CELL LINE; ULTRAVIOLET RADIATION; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; CELL LINE, TUMOR; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; MICE; QUINOLONES; SINGLET OXYGEN; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPEROXIDES; ULTRAVIOLET RAYS;

MURINAE;

EID: 78650648706     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2010.00832.x     Document Type: Article

References (69)

1. Golub, A., O. Yakovenko, V. Bdzhola, V. Sapelkin, P. Zien, and, S. Yarmoluk, (2006) Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2. J. Med. Chem. 49, 6443-6450.
2. Boteva, A., and, O. Krasnykh, (2009) The methods of synthesis, modification, and biological activity of 4-quinolones (Review). Chem. Heterocycl. Compd. 45, 757-785.
3. Andersson, M., and, A. MacGowan, (2003) Development of the quinolones. J. Antimicrob. Chemother. 51, 1-11.
4. Adam, H. J., N. M. Laing, C. R. King, B. Lulashnyk, D. J. Hoban, and, G. G. Zhanel, (2009) In vitro activity of nemonoxacin, a novel nonfluorinated quinolone, against 2,440 clinical isolates. Antimicrob. Agents Chemother. 53, 4915-4920.
5. Azema, J., B. Guidetti, J. Dewelle, B. Le Calve, T. Mijatovic, A. Korolyov, J. Vaysse, M. Malet-Martino, R. Martino, and, R. Kiss, (2009) 7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: Synthesis and in vitro biological evaluation as potential antitumor agents. Bioorg. Med. Chem. 17, 5396-5407.
6. Diaz, M., S. Calaforra, E. Ibanez, A. Giner, R. Almero, D. Sanz, and, A. Campos, (2009) Challenge tests with quinolones. Allergy 64, 291-292.
7. Dinakaran, M., P. Senthilkumar, P. Yogeeswari, A. China, V. Nagaraja, and, D. Sriram, (2008) Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation. Bioorg. Med. Chem. Lett. 18, 1229-1236.
8. Stahlmann, R., (2002) Clinical toxicological aspects of fluoroquinolones. Toxicol. Lett. 127, 269-277.
9. Heller, M., (2008) FDA alert of quinolones and phototoxicity. J. Drugs Dermatol. 7, 501-501.
10. Mang, R., H. Stege, and, J. Krutmann, (2006) Mechanisms of phototoxic and photoallergic reactions. In Contact Dermatitis (Edited by, P. J. Frosch, T. Menné, and, J.-P. Lepoittevin,), pp. 97-104. Springer, Berlin.
11. Stein, K., and, N. Scheinfeld, (2007) Drug-induced photoallergic and phototoxic reactions. Expert Opin. Drug Safety 6, 431-443.
12. Neumann, N., A. Blotz, G. Wasinska-Kempka, M. Rosenbruch, P. Lehmann, H. Ahr, and, H. Vohr, (2005) Evaluation of phototoxic and photoallergic potentials of 13 compounds by different in vitro and in vivo methods. J. Photochem. Photobiol. B, Biol. 79, 25-34.
13. Rosen, J., (1997) Proposed mechanism for the photodynamic generation of 8-oxo-7,8-dihydro-2'-deoxyguanosine produced in cultured cells by exposure to lomefloxacin. Mut. Res. Fund. Mol. Mechan. Mutagen. 381, 117-129.
14. Fasani, E., A. Profumo, and, A. Albini, (1998) Structure and medium-dependent photodecomposition of fluoroquinolone antibiotics. Photochem. Photobiol. 68, 666-674.
15. Rosen, J., A. Prahalad, G. Schluter, D. Chen, and, G. Williams, (1997) Quinolone antibiotic photodynamic production of 8-oxo-7,8-dihydro-2'- deoxyguanosine in cultured liver epithelial cells. Photochem. Photobiol. 65, 990-996.
16. Agrawal, N., R. Ray, M. Farooq, A. Pant, and, R. Hans, (2007) Photosensitizing potential of ciprofloxacin at ambient level of UV radiation. Photochem. Photobiol. 83, 1226-1236.
17. Cuquerella, M., F. Bosca, M. Miranda, A. Belvedere, A. Catalfo, and, G. de Guidi, (2003) Photochemical properties of ofloxacin involved in oxidative DNA damage: A comparison with rufloxacin. Chem. Res. Toxicol. 16, 562-570.
18. Hayashi, N., Y. Nakata, and, A. Yazaki, (2004) New findings on the structure-phototoxicity relationship and photostability of fluoroquinolones with various substituents at position 1. Antimicrob. Agents Chemother. 48, 799-803.
19. Fasani, E., S. Monti, I. Manet, F. Tilocca, L. Pretali, M. Mella, and, A. Albini, (2009) Inter- and intramolecular photochemical reactions of fleroxacin. Org. Lett. 11, 1875-1878.
20. Martinez, L., G. Li, and, C. Chignell, (1997) Photogeneration of fluoride by the fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin. Photochem. Photobiol. 65, 599-602.
21. Martinez, L., R. Sik, and, C. Chignell, (1998) Fluoroquinolone antimicrobials: Singlet oxygen, superoxide and phototoxicity. Photochem. Photobiol. 67, 399-403.
22. Sanchez, G., M. Hidalgo, J. Vivanco, and, J. Escobar, (2005) Induced and photoinduced DNA damage by quinolones: Ciprofloxacin, ofloxacin and nalidixic acid determined by comet assay. Photochem. Photobiol. 81, 819-822.
23. Sauvaigo, S., T. Douki, F. Odin, S. Caillat, J. L. Ravanat, and, J. Cadet, (2001) 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. Photochem. Photobiol. 73, 230-237.
24. Ribeiro, J. N., A. R. da Silva, and, R. A. Jorge, (2004) Involvement of mitochondria in apoptosis of cancer cells induced by photodynamic therapy. J. Bras. Patol Med. Lab. 40, 383-390.
25. Wainwright, M., (1998) Photodynamic antimicrobial chemotherapy (PACT). J. Antimicrob. Chemother. 42, 13-28.
26. Wainwright, M., (2008) Photodynamic therapy: The development of new photosensitisers. Anti-Cancer Agents Med. Chem. 8, 280-291.
27. g) production by 9H-fluoren-9-one: Solvents and solvent mixtures. Helv. Chim. Acta 86, 384-397.
28. Martinez, L., and, C. Chignell, (1998) Photocleavage of DNA by the fluoroquinolone antibacterials. J. Photochem. Photobiol. B: Biol. 45, 51-59.
29. Bella, M., M. Schultz, V. Milata, K. Koňariková, and, M. Breza, (2010) Application of the Gould-Jacobs reaction to 4- aminobenzoselenadiazole. Tetrahedron 66, 8169-8174.
30. Padmavathi, V., A. Padmaja, and, D. Reddy, (1999) Selena and thiadiazole fused heterocycles. Indian J. Chem., Sect. B 38, 308-311.
31. Jebaraj, J., M. Gopalakrishnan, and, G. Baskar, (2008) Synthesis and spectral analysis of some 4-substituted-5,7-diarylpyridino[3,4-d]-1,2,3- selenadiazoles. Asian J. Chem. 20, 5215-5222.
32. Jantová, S., S. Letašiová, K. Koň ariková, V. Milata, and, V. Brezová, (2010) Effect of new synthetically prepared quinolone ethyl-1,4-dihydro-8-nitro-4-oxoquinoline-3- carboxylate on human leukemia cell line HL-60 without/with presence of UVA irradiation. Acta Chim. Slovaca 3, 51-72.
33. Jantová, S., S. Letašiová, V. Brezová, A. Čipák, and, J. Lábaj, (2006) Photochemical and phototoxic activity of berberine on murine fibroblast NIH-3T3 and Ehrlich ascites carcinoma cells. J. Photochem. Photobiol. B, Biol. 85, 163-176.
34. Zang, L., F. vanKuijk, B. Misra, and, H. Misra, (1995) The specificity and product of quenching singlet oxygen by 2,2,6,6-tetramethylpiperidine. Biochem. Mol. Biol. Int. 37, 283-293.
35. Rajendran, A., R. Gandhidasan, and, R. Murugesan, (2004) Photosensitisation and photoinduced DNA cleavage by four naturally occurring anthraquinones. J. Photochem. Photobiol. A, Chem. 168, 67-73.
36. Kuhn, H. J., S. E. Braslavsky, and, R. Schmidt, (2004) Chemical actinometry (UIPAC technical report). Pure Appl. Chem. 76, 2105-2146.
37. NIEHS (2002) WinSIM, NIEHS, Research Triangle Park, NC, USA. Available at:. Accessed on 15 October 2010.
38. Jantová, S., (2009) Viability, proliferation and death of cells cultivated in in vitro conditions. Slovak University of Technology, Bratislava, Slovak Republic.
39. Bevilaqua, T., T. Goncalves, C. Venturini, and, V. Machado, (2006) Solute-solvent and solvent-solvent interactions in the preferential solvation of 4-[4-(dimethylamino)styryl]-1-methylpyridinium iodide in 24 binary solvent mixtures. Spectrochim. Acta, Part A 65, 535-542.
40. •-, electrochemically generated in DMSO at room temperature. Electrochim. Acta 53, 3412-3415.
41. Wadhawan, J., P. Welford, H. McPeak, C. Hahn, and, R. Compton, (2003) 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. Sens. Actuators B, Chem. 88, 40-52.
42. Jenny, T. A., and, N. J. Turro, (1982) Solvent and deuterium isotope effects on the lifetime of singlet oxygen determined by direct emission spectroscopy at 1.27 μm. Tetrahedron Lett. 23, 2923-2926.
43. Santos, F., P. Abreu, H. Castro, I. Paixao, C. Cirne-Santos, V. Giongo, J. Barbosa, B. Simonetti, V. Garrido, D. Bou-Habib, D. Silva, P. Batalha, J. Temerozo, T. Souza, C. Nogueira, A. Cunha, C. Rodrigues, V. Ferreira, and, M. de Souza, (2009) Synthesis, antiviral activity and molecular modeling of oxoquinoline derivatives. Bioorg. Med. Chem. 17, 5476-5481.
44. De la Cruz, A., J. Elguero, P. Goya, A. Martinez, and, W. Pfleiderer, (1992) Tautomerism and acidity in 4-quinolone-3-carboxylic acid derivatives. Tetrahedron 48, 6135-6150.
45. Gao, J., and, L. Shao, (1994) Polarization effects on the tautomeric equilibria of 2-hydroxypyridine and 4-hydroxypyridine in aqueous and organic solution. J. Phys. Chem. 98, 13772-13779.
46. Mphahlele, M., and, A. El-Nahas, (2004) Tautomeric 2-arylquinolin-4(1H)- one derivatives-spectroscopic, X-ray and quantum chemical structural studies. J. Mol. Struct. 688, 129-136.
47. Belal, F., A. Al-Majed, and, A. Al-Obaid, (1999) Methods of analysis of 4-quinolone antibacterials. Talanta 50, 765-786.
48. Brezová, V., S. Gabčová, D. Dvoranová, and, A. Staško, (2005) Reactive oxygen species produced upon photoexcitation of sunscreens containing titanium dioxide (an EPR study). J. Photochem. Photobiol. B, Biol. 79, 121-134.
49. Noda, H., K. Oikawa, H. Ohya-Nishiguchi, and, H. Kamada, (1993) Detection of superoxide ions from photoexcited semiconductors in non-aqueous solvents using the ESR spin-trapping technique. Bull. Chem. Soc. Jpn. 66, 3542-3547.
50. Herscu-Kluska, R., A. Masarwa, M. Saphier, H. Cohen, and, D. Meyerstein, (2008) Mechanism of the reaction of radicals with peroxides and dimethyl sulfoxide in aqueous solution. Chem. Eur. J. 14, 5880-5889.
51. Dikalov, S., and, R. Mason, (1999) Reassignment of organic peroxyl radical adducts. Free Radic. Biol. Med. 27, 864-872.
52. • and DMSO: LC/ESR, LC/MS, and dual spin trapping combinations. Free Radic. Biol. Med. 38, 125-135.
53. Dikalov, S., and, R. Mason, (2001) Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals: Reassignment to alkoxyl radical adducts. Free Radic. Biol. Med. 30, 187-197.
54. 2 process using polychromatic radiation sources. Photochem. Photobiol. Sci. 1, 520-525.
55. Chalier, F., and, P. Tordo, (2002) 5-Diisopropoxyphosphoryl-5-methyl-1- pyrroline N-oxide, DIPPMPO, a crystalline analog of the nitrone DEPMPO: Synthesis and spin trapping properties. J. Chem. Soc. Perkin Trans. 2, 2110-2117.
56. Frejaville, C., H. Karoui, B. Tuccio, F. Lemoigne, M. Culcasi, S. Pietri, R. Lauricella, and, P. Tordo, (1994) 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-centered radicals. J. Chem. Soc. Chem. Commun. 1793-1794.
57. Olive, G., A. Mercier, F. Le Moigne, A. Rockenbauer, and, P. Tordo, (2000) 2-Ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide: evaluation of the spin trapping properties. Free Radic. Biol. Med. 28, 403-408.
58. Tuccio, B., A. Zeghdaoui, J. Finet, V. Cerri, and, P. Tordo, (1996) Use of new beta-phosphorylated nitrones for the spin trapping of free radicals. Res. Chem. Intermed. 22, 393-404.
59. •- spin trap adducts with super-hyperfine structure in their EPR spectra: An alternative EPR spin trapping assay for radical scavenging capacity determination in dimethylsulphoxide. Free Radic. Res. 43, 457-469.
60. Rockenbauer, A., J. Clement, M. Culcasi, A. Mercier, P. Tordo, and, S. Pietri, (2007) 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. J. Phys. Chem. A 111, 4950-4957.
61. Dikalov, S., P. Tordo, A. Motten, and, R. Mason, (2003) Characterization of the high resolution ESR spectra of the methoxyl radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO). Free Radic. Res. 37, 705-712.
62. Dikalov, S., J. Jiang, and, R. Mason, (2005) 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. Free Radic. Res. 39, 825-836.
63. Stolze, K., N. Udilova, T. Rosenau, A. Hofinger, and, H. Nohl, (2005) Spin adduct formation from lipophilic EMPO-derived spin traps with various oxygen- and carbon-centered radicals. Biochem. Pharmacol. 69, 297-305.
64. Stolze, K., N. Rohr-Udilova, T. Rosenau, A. Hofinger, D. Kolarich, and, H. Nohl, (2006) Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives. Bioorg. Med. Chem. 14, 3368-3376.
65. Stolze, K., N. Udilova, and, H. Nohl, (2002) Spin adducts of superoxide, alkoxyl, and lipid-derived radicals with EMPO and its derivatives. Biol. Chem. 383, 813-820. (Pubitemid 34649900)
66. Stolze, K., N. Rohr-Udilova, A. Hofinger, and, T. Rosenau, (2008) Spin trapping experiments with different carbamoyl-substituted EMPO derivatives. Bioorg. Med. Chem. 16, 8082-8089.
67. - donor. Free Radic. Res. 43, 581-593.
68. Brezová, V., P. Tarábek, D. Dvoranová, A. Staško, and, S. Biskupič, (2003) EPR study of photoinduced reduction of nitroso compounds in titanium dioxide suspensions. J. Photochem. Photobiol. A, Chem. 155, 179-198.
69. Inbaraj, J., R. Gandhidasan, and, R. Murugesan, (1999) Photodynamic action of some naturally occurring quinones: Formation of reactive oxygen species. J. Photochem. Photobiol. A, Chem. 124, 95-99.