Properties of the radical intermediate obtained on oxidation of 2′,7′-dichlorodihydrofluorescein, a probe for oxidative stress

Free Radical Biology and Medicine

Volumn 41, Issue 4, 2006, Pages 657-667

  Wrona, Marta ^a   Wardman, Peter ^a  

^a MOUNT VERNON HOSPITAL   (United Kingdom)

Author keywords

Dichlorodihydrofluorescein; Fluorescent probes; pKa; Pulse radiolysis; Reduction potential

Indexed keywords

DICHLOROFLUORESCEIN; FLAVOPROTEIN; HYDROGEN PEROXIDE; OXIDOREDUCTASE; OXYGEN; SEMIQUINONE; SUPEROXIDE;

ABSORPTION; ARTICLE; BIOLOGY; CATALYST; KINETICS; MONITORING; OXIDATION REDUCTION POTENTIAL; OXIDATIVE STRESS; PH; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

EID: 33746099288     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2006.05.006     Document Type: Article

References (38)

1. Keston A.S., and Brandt R. The fluorimetric analysis of ultramicro quantities of hydrogen peroxide. Anal. Biochem. 11 (1965) 1-5
2. Cathcart R., Schwiers E., and Ames B.N. Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescein assay. Anal. Biochem. 134 (1983) 111-116
3. Rothe G., and Valet G. Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,7′-dichlorofluorescin. J. Leukocyte Biol. 47 (1990) 440-448
4. 2 in cultured endothelial cells. Arch. Biochem. Biophys. 302 (1993) 348-355
5. Rota C., Chignell C.F., and Mason R.P. Evidence for free radical formation during the oxidation of 2′-7′-dichlorofluorescin to the fluorescent dye 2′-7′-dichlorofluorescein by horseradish peroxidase: possible implications for oxidative stress measurements. Free Radic. Biol. Med. 27 (1999) 873-881
6. Burkitt M.J., and Wardman P. Cytochrome c is a potent catalyst of dichlorofluorescin oxidation: implications for the role of reactive oxygen species in apoptosis. Biochem. Biophys. Res. Commun. 282 (2001) 329-333
7. Ohashi T., Mizutani A., Murakami A., Kojo S., Ishii T., and Taketani S. Rapid oxidation of dichlorodihydrofluorescin with heme and hemoproteins: formation of the fluorescein is independent of the generation of reactive oxygen species. FEBS Lett. 511 (2002) 21-27
8. 2: implications for oxidative stress during apoptosis. J. Biol. Chem. 278 (2003) 29410-29419
9. LeBel C.P., Ischiropoulos H., and Bondy S.C. Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem. Res. Toxicol. 5 (1992) 227-231
10. Crow J.P. Dichlorofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: implications for intracellular measurements of reactive nitrogen and oxygen species. Nitric Oxide 1 (1997) 145-157
11. Glebska J., and Koppenol W.H. Peroxynitrite-mediated oxidation of dichlorodihydrofluorescein and dihydrorhodamine. Free Radic. Biol. Med. 35 (2003) 676-682
12. Wrona M., Patel K.B., and Wardman P. Reactivity of 2′,7′-dichlorodihydrofluorescein and dihydrorhodamine 123 and their oxidized forms towards carbonate, nitrogen dioxide, and hydroxyl radicals. Free Radic. Biol. Med. 38 (2005) 262-270
13. Marchesi E., Rota C., Fann Y.C., Chignell C.F., and Mason R.P. Photoreduction of the fluorescent dye 2′-7′-dichlorofluorescein: a spin trapping and direct electron spin resonance study with implications for oxidative stress measurements. Free Radic. Biol. Med. 26 (1999) 148-161
14. Bonini M.G., Rota C., Tomasi A., and Mason R.P. The oxidation of 2′,7′-dichlorofluorescin to reactive oxygen species: a self-fulfilling prophecy?. Free Radic. Biol. Med. 40 (2006) 968-975
15. O'Malley Y.Q., Reszka K.J., and Britigan B.E. Direct oxidation of 2′,7′-dichlorodihydrofluorescein by pyocyanin and other redox-active compounds independent of reactive oxygen species production. Free Radic. Biol. Med. 36 (2004) 90-100
16. Rota C., Fann Y.C., and Mason R.P. Phenoxyl free radical formation during the oxidation of the fluorescent dye 2′,7′-dichlorofluorescein by horseradish peroxidase. J. Biol. Chem. 274 (1999) 28161-28168
17. Wardman P., Burkitt M.J., Patel K.B., Lawrence A., Jones C.M., Everett S.A., and Vojnovic B. Pitfalls in the use of common luminescent probes for oxidative and nitrosative stress. J. Fluoresc. 12 (2002) 65-68
18. Cenas N., Anusevicius Z., Bironaité D., Bachmanova G.L., Archakov A.I., and Öllinger K. The electron transfer reactions of NADPH:cytochrome P450 reductase with nonphysiological oxidants. Arch. Biochem. Biophys. 315 (1994) 400-406
19. Candeias L.P., Folkes L.K., Dennis M.F., Patel K.B., Everett S.A., Stratford M.R.L., and Wardman P. Free-radical intermediates and stable products in the oxidation of indole-3-acetic acid. J. Phys. Chem. 98 (1994) 10131-10137
20. Buxton G.V., and Stuart C.R. Re-evaluation of the thiocyanate dosimeter for pulse radiolysis. J. Chem. Soc. Faraday Trans. 91 (1995) 279-281
21. Ross A.B., Mallard W.G., Helman W.P., Buxton G.V., Huie R.E., and Neta P. NDRL-NIST solution kinetics database version 3 (1998), Notre Dame, IN, Notre Dame Radiation Laboratory and National Institute of Standards and Technology
22. Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data 18 (1989) 1637-1755
23. Wardman P. The reduction potential of benzyl viologen: an important reference compound for oxidant/radical redox couples. Free Radic. Res. Commun. 14 (1991) 57-67
24. Albert A., and Serjeant E.P. The determination of ionization constants: a laboratory manual (1984), Chapman & Hall, London
25. Clark W.M. Oxidation-reduction potentials of organic systems (1960), Williams & Wilkins, Baltimore
26. Bell R.P. The proton in chemistry (1959), Methuen, London
27. Capellos C., and Bielski B.H.J. Kinetic systems: mathematical description of chemical kinetics in solution (1972), Wiley, New York
28. Mchedlov-Petrossyan N.O., Rubtsov M.I., and Lukatskaya L.L. Ionization and tautomerism of chloro-derivatives of fluorescein in water and aqueous acetone. Dyes Pigments 1992 (1992) 18
29. Leonhardt H., Gordon L., and Livingston R. Acid-base equilibria of fluorescein and 2′-7′-dichlorofluorescein in their ground and fluorescent states. J. Phys. Chem. 75 (1971) 245-249
30. Issa I.M., El-Samahy A.A., Issa R.M., and Ghoneim M.M. Polarography of dihalogen fluoresceins in solutions of varying pH at the DME. Electrochim. Acta 17 (1972) 1195-1202
31. Perlmutter-Hayman B. The primary kinetic salt-effect in aqueous solution. Prog. React. Kinet. 6 (1971) 239-267
32. Lindqvist L. A flash photolysis study of fluorescein. Ark. Kemi 16 (1960) 79-138
33. Cordier P., and Grossweiner L.I. Pulse radiolysis of aqueous fluorescein. J. Phys. Chem. 72 (1968) 2018-2026
34. Cadenas E., and Davies K.J.A. Mitochondrial free radical generation, oxidative stress, and aging. Free Radic. Biol. Med. 29 (2000) 222-230
35. Dunford H.B. Heme peroxidases (1999), Wiley-VCH, New York
36. Roos A., and Boron W.F. Intracellular pH. Physiol. Rev. 61 (1981) 296-434
37. Wardman P., and von Sonntag C. Kinetic factors that control the fate of thiyl radicals in cells. Methods Enzymol. 251 (1995) 31-45
38. Surdhar P.S., and Armstrong D.A. Reduction potentials and exchange reactions of thiyl radicals and disulfide anion radicals. J. Phys. Chem. 91 (1987) 6532-6537