Photophysical properties of the prefluorescent nitroxide probes QT and C343T

Photochemistry and Photobiology

Volumn 84, Issue 6, 2008, Pages 1535-1542

  Bueno, Claudia ^a   Mikelsons, Larisa ^b   Maretti, Luca ^b   Scaiano, J C ^b   Aspée, Alexis ^a  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDE; FLUORESCENT DYE; FREE RADICAL; ION; NITRIC OXIDE; QUINOLINOL DERIVATIVE; QUINOLIZINE DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICELLE; PH; PHOTOCHEMISTRY; RADIATION EXPOSURE; SPECTROPHOTOMETRY; TIME;

CYCLIC N-OXIDES; FLUORESCENT DYES; FREE RADICALS; HYDROGEN-ION CONCENTRATION; HYDROXYQUINOLINES; IONS; MICELLES; MOLECULAR STRUCTURE; NITRIC OXIDE; PHOTOCHEMICAL PROCESSES; QUINOLIZINES; SOLVENTS; SPECTROPHOTOMETRY; TIME FACTORS;

EID: 55649105629     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2008.00381.x     Document Type: Article

References (43)

1. Likhteinstein, G. I., K. Ishii S. Nakatsuji (2007) Dual chromophore-nitroxides: novel molecular probes, photochemical and photophysical models and magnetic materials. Photochem. Photobiol. 83, 871 881.
2. Kieber, D. J. N. V. Blough (1990) Fluorescence detection of carbon-centered radicals in aqueous solution. Free Radic. Res. 10, 109 117.
3. Moad, G., D. Shipp, T. A. Smith D. H. Solomon (1999) Measurements of primary radical concentrations generated by pulsed laser photolysis using fluorescence detection. J. Phys. Chem. A 103, 6580 6586.
4. Kieber, D. J. N. V. Blough (1990) Determination of carbon-centered radicals in aqueous solution by liquid chromatography with fluorescence detection. Anal. Chem. 62, 2275 2283.
5. Gerlock, J. L., P. J. Zacmanidis, D. R. Bauer, D. J. Simpson, N. V. Blough I. T. Salmeen (1990) Fluorescence detection of free radicals by nitroxide scavenging. Free Radic. Res. Commun. 10, 119 121.
6. Aspée, A., O. García, L. Maretti, R. Sastre J. C. Scaiano (2003) Free radical reactions in poly(methylmethacrylate) films monitored using a pre-fluorescent quinoline-Tempo sensor. Macromolecules 36, 3550 3556.
7. Coenjarts, C., O. García, L. Llauger, J. Palfreyman, A. Vinette J. C. Scaiano (2003) Mapping photogenerated radicals in thin polymer films: Fluorescence imaging using a pre-fluorescent radical probe. J. Am. Chem. Soc. 125, 620 621.
8. Aspée, A., L. Maretti J. C. Scaiano (2003) Monitoring photodecomposition of dibenzyl ketone within NaY zeolite with a pre-fluorescent nitroxide compound. Photochem. Photobiol. Sci. 2, 1125 1129.
9. Green, S. A., D. J. Simpson, G. Zhou, P. S. Ho N. V. Blough (1990) Intramolecular quenching of excited singlet states by stable nitroxide radicals. J. Am. Chem. Soc. 112, 7337 7346.
10. Blough, N. V. D. J. Simpson (1988) Chemically mediated fluorescence yield switching in nitroxide fluorophore adducts: optical sensors of radical/redox reactions. J. Am. Chem. Soc. 110, 1915 1917.
11. Papper, V., N. Medvedeva, I. Fishov G. I. Likhtenshtein (2000) Quenching of cascade reaction between triple and photochrome probes with nitroxide radicals. Appl. Biochem. Biotechnol. 89, 231 248.
12. Pou, S., A. Bhan, V. S. Bhadti, S. Y. Wu, R. S. Hosmane G. M. Rosen (1995) The use of fluorophore-containing spin traps as potential probes to localize free radicals in cells with fluorescence imaging methods FASEB J. 9, 1085 1090.
13. Li, B., P. L. Gutierrez N. V. Blough (1997) Trace determination of hydroxyl radicals in biological systems. Anal. Chem. 69, 4295 4302.
14. Pou, S., Y.-I. Huang, A. Bhan, V. S. Bhadti, R. S. Hosmane, S. Y. Wu, G.-L. Cao G. M. A. Rosen (1993) A fluorophore-containing nitroxide as a probe to detect superoxide and hydroxyl radical generated by stimulated neutrophils. Anal. Biochem. 212, 85 90.
15. Li, B., N. V. Blough P. L Gutierrez (2000) Trace detection of hydroxyl radicals during the redox cycling of low concentrations of diaziquone: A new approach. Free Radic. Biol. Med. 29, 548 556.
16. Yang, X. F. X. Q. Guo (2001) Investigation of the anthracene-nitroxide hybrid molecule as a probe for hydroxyl radicals. Analyst 126, 1800 18004.
17. Borisenko, G. G., I. Martin, Q. Zhao, A. A. Amoscato, Y. Y. Tyurina V. E. Kagan (2004) Glutathione propagates oxidative stress triggered by myeloperoxidase in HL-60 cells. J. Biol. Chem. 279, 23453 23462.
18. Swartz, H. M. (1990) The use of nitroxides in viable biological systems: An opportunity and challenge for chemists and biochemists. Pure Appl. Chem. 62, 235 239.
19. Zhang, Y. W.-W. Fung (1994) The roles of ascorbic acid and other antioxidants in the erythrocyte in reducing membrane nitroxide radicals. Free. Radic. Biol. Med. 16, 215 222.
20. May, J. M., Z.-C. Qu, S. Juliao C. E. Coob (2005) Ascorbic acid decreases oxidant stress in endothelial cells caused by the nitroxide tempol. Free Radic. Res. 39, 195 202.
21. Lozinsky, E., V. V. Martin, T. A. Berezina, A. I. Shames, A. L. Weis G. I. Lickhteinshtien (1999) Dual fluorophore-nitroxide probes for analysis of vitamin C in biological liquids. J. Biochem. Biophys. Methods 38, 29 42.
22. Saphier, O., T. Silberstein, A. I. Shames, G. I. Licktenshtein, E. Maimon, D. Mankuta, M. Mazor, M. Katz, D. Meyerstein N. Meyerstein (2003) The reduction of a nitroxide spin label as a probe of human blood antioxidant properties. Free Radic. Res. 37, 301 308.
23. Aliaga, C., A. Aspée J. C. Scaiano (2003) A new method to study antioxidant capability: Hydrogen transfer from phenols to a pre-fluorescent nitroxide. Org. Lett. 5, 4145 4148.
24. Aliaga, C., D. Stuart, A. Aspée J. C. Scaiano (2005) Solvent effects on hydrogen abstraction reactions from lactones with antioxidant properties. Org. Lett. 7, 3665 3668.
25. Aspée, A., C. Aliaga J. C. Scaiano (2007) Transient enol isomers of dibenzoylmethane and avobenzone as efficient hydrogen donors towards a nitroxide pre-fluorescent probe. Photochem. Photobiol. 83, 481 485.
26. Ahrens, B. B., M. G. Davidson, V. T. Forsyth, M. F. Mahon, A. L. Johnson, S. A. Mason, R. D. Price S. A. Raithby (2001) Neutron diffraction study of a phenol·nitroxide radical adduct: A structural model for hydrogen atom abstraction by peroxyl radicals from vitamin E and related phenolic antioxidants. J. Am. Chem. Soc. 123, 9164.
27. Litwinienko, G. K. U. Ingold (2003) Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1- picrylhydrazyl (DPPH) in alcohols. J. Org. Chem. 68, 3433 3438.
28. Aspée, A., C. Bueno, J. M. Villarreal, C. Saaverdra, L. Mikelsons J. C. Scaiano (2006) Photophysical Properties of Nitroxide Pre-fluorescent Probes and Their Potential Use to Study Biological Systems. 17th Inter-American Photochemical Society Winter Conference (IAPS), Salvador, Bahia, Brazil, June 11-16.
29. Subczynski, W. K., J. Wojas, V. Pezeshk A. Pezeshk (1998) Partitioning and localization of spin-labeled amantadine in lipid bilayers: An EPR study. J. Pharm. Sci. 87, 1249 1254.
30. Mravljak, J., R. Zeisig S. Peĉar (2005) Synthesis and biological evaluation of spin-labeled alkylphospholipid analogs. J. Med. Chem. 48, 6393 6399.
31. Kocherginsky, N. H. M. Swartz (1995) Nitroxide Spin Labels: Reactions in Biology and Chemistry. CRC Press, Boca Raton, FL.
32. Kokliĉ, T., M. Ŝentjurc R. Zeisig (2002) The influence of cholesterol and charge on the membrane domains of alkylphospholipid liposomes as studied by EPR. J. Liposome Res. 12, 335 352.
33. Smith, M. B. J. March (2001) March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th edn, Wiley & Sons, New York.
34. Dolman, D. R. A. Stewart (1967) Comparison of the acidity and basicity of aromatic amines. Can. J. Chem. 45, 925 928.
35. Ribeiro, A. M. H. Chaimovich (1983) Preparation and characterization of large dioctadecyldimethylamonium chloride liposomes and comparison with small sonicated vesicles. Biochim. Biocphys. Acta 733, 172 179.
36. Göktürk, S., R. Y. Talman, N. Erdinc M. Tuncay (2006) Solution behaviour of rivanol in micellar environments. Spectrosc. Lett. 39, 357 372.
37. Bueno, C. M. V. Encinas (2003) Photophysical and photochemical studies of pyradoxamine. Helv. Chim. Acta 86, 3363 3375.
38. Bueno, C., J. Guerrero M. V. Encinas (2004) Spectroscopic properties of 4-pyridoxic acid as a function of pH and solvent. Helv. Chim. Acta 87, 940 948.
39. Ivan, M. J. C. Scaiano (2003) A new approach for the detection of carbon-centered radicals in enzymatic processes using pre-fluorescent probes. Photochem. Photobiol. 78, 416 419.
40. El-Kemary, M. W. Retting (2003) Multiple emission in coumarins with heterocyclic substituents. Phys. Chem. Chem. Phys. 5, 5221 5228.
41. Jones, G., W. Jackson C.-Y. Choi (1985) Solvent effect on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism. J. Phys. Chem. 89, 294 300.
42. Correa, N. M. N. E. Levinger (2006) What can you learn from a molecular probe? New insights on the behavior of C343 in homogeneous solutions and AOT reverse micelles J. Phys. Chem. B 110, 13050 13061.
43. J. R. Lakowicz (ed 1994) Topics in Fluorescence Spectroscopy: Probe Design and Chemical Sensing, Vol. 4, pp. 183 222. Plenum Publishing, New York.