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Volumn 38, Issue 2, 2005, Pages 262-270

Reactivity of 2′,7′-dichlorodihydrofluorescein and dihydrorhodamine 123 and their oxidized forms toward carbonate, nitrogen dioxide, and hydroxyl radicals

Author keywords

Carbonate radical; Dichlorodihydrofluorescein; Dihydrorhodamine; Fluorescent probes; Free radicals; Hydroxyl radical; Nitrogen dioxide

Indexed keywords

2',7' DICHLORODIHYDROFLUORESCEIN; ANTIOXIDANT; CARBONIC ACID; FLUORESCEIN DERIVATIVE; HYDROXYL RADICAL; NITROGEN DIOXIDE; RHODAMINE 123; UNCLASSIFIED DRUG; 2',7'-DICHLORODIHYDROFLUORESCEIN; CARBONIC ACID DERIVATIVE; DIHYDRORHODAMINE 123; FREE RADICAL; OXYGEN; RHODAMINE;

EID: 10844237083     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.10.022     Document Type: Article
Times cited : (165)

References (50)
  • 1
    • 0030781227 scopus 로고    scopus 로고
    • Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis
    • R. Kissner, T. Nauser, P. Bugnon, and W. Koppenol Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis Chem. Res. Toxicol. 10 1997 1285 1292
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1285-1292
    • Kissner, R.1    Nauser, T.2    Bugnon, P.3    Koppenol, W.4
  • 3
    • 0035954378 scopus 로고    scopus 로고
    • Nitration and oxidation of a hydrophobic tyrosine probe by peroxynitrite in membranes: Comparison with nitration and oxidation of tyrosine by peroxynitrite in aqueous solution
    • H. Zhang, J. Joseph, J. Feix, N. Hogg, and B. Kalyanaraman Nitration and oxidation of a hydrophobic tyrosine probe by peroxynitrite in membranes: comparison with nitration and oxidation of tyrosine by peroxynitrite in aqueous solution Biochemistry 40 2001 7675 7686
    • (2001) Biochemistry , vol.40 , pp. 7675-7686
    • Zhang, H.1    Joseph, J.2    Feix, J.3    Hogg, N.4    Kalyanaraman, B.5
  • 4
    • 0031769737 scopus 로고    scopus 로고
    • Peroxynitrite studied by stopped-flow spectroscopy
    • R. Kissner, J. Beckman, and W. Koppenol Peroxynitrite studied by stopped-flow spectroscopy Methods Enzymol. 301 1999 342 352
    • (1999) Methods Enzymol. , vol.301 , pp. 342-352
    • Kissner, R.1    Beckman, J.2    Koppenol, W.3
  • 5
    • 0031857054 scopus 로고    scopus 로고
    • Mechanisms of peroxynitrite oxidations and rearrangements: The theoretical perspective
    • M. Bartberger, L. Olson, and K. Houk Mechanisms of peroxynitrite oxidations and rearrangements: the theoretical perspective Chem. Res. Toxicol. 11 1998 710 711
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 710-711
    • Bartberger, M.1    Olson, L.2    Houk, K.3
  • 6
    • 0025874048 scopus 로고
    • Peroxynitrite-induced membrane lipid peroxidation: The cytotoxic potential of superoxide and nitric oxide
    • R. Radi, J. Beckman, K. Bush, and B. Freeman Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide Arch. Biochem. Biophys. 288 1991 481 487
    • (1991) Arch. Biochem. Biophys. , vol.288 , pp. 481-487
    • Radi, R.1    Beckman, J.2    Bush, K.3    Freeman, B.4
  • 7
    • 0029805172 scopus 로고    scopus 로고
    • Nitric oxide, superoxide, and peroxynitrite: The good, the bad, and ugly
    • J. Beckman, and W. Koppenol Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and ugly Am. J. Physiol. 271 1996 C1424 C1437
    • (1996) Am. J. Physiol. , vol.271
    • Beckman, J.1    Koppenol, W.2
  • 9
    • 0032171410 scopus 로고    scopus 로고
    • Oxidative chemistry of nitric oxide: The roles of superoxide, peroxynitrite, and carbon dioxide
    • G. Squadrito, and W. Pryor Oxidative chemistry of nitric oxide: the roles of superoxide, peroxynitrite, and carbon dioxide Free Radic. Biol. Med. 25 1998 392 403
    • (1998) Free Radic. Biol. Med. , vol.25 , pp. 392-403
    • Squadrito, G.1    Pryor, W.2
  • 10
    • 0033574624 scopus 로고    scopus 로고
    • Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide
    • M. Bonini, R. Radi, G. Ferrer-Sueta, A. Ferreira, and O. Augusto Direct EPR detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide J. Biol. Chem. 274 1999 10802 10806
    • (1999) J. Biol. Chem. , vol.274 , pp. 10802-10806
    • Bonini, M.1    Radi, R.2    Ferrer-Sueta, G.3    Ferreira, A.4    Augusto, O.5
  • 14
    • 0026554428 scopus 로고
    • Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress
    • C. LeBel, H. Ischiropoulos, and S. Bondy 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
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 227-231
    • Lebel, C.1    Ischiropoulos, H.2    Bondy, S.3
  • 15
    • 0032783532 scopus 로고    scopus 로고
    • Dihydrofluorescein diacetate is superior for detecting intracellular oxidants: Comparison with 2′,7′-dichlorodihydrofluorescein diacetate, 5(and 6)-carboxy-2′,7′-dichlorodihydrofluorescein diacetate, and dihydrorhodamine 123
    • S. Hempel, G. Buettner, Y. O'Malley, D. Wessels, and D. Flaherty Dihydrofluorescein diacetate is superior for detecting intracellular oxidants: comparison with 2′,7′-dichlorodihydrofluorescein diacetate, 5(and 6)-carboxy-2′,7′-dichlorodihydrofluorescein diacetate, and dihydrorhodamine 123 Free Radic. Biol. Med. 27 1999 146 159
    • (1999) Free Radic. Biol. Med. , vol.27 , pp. 146-159
    • Hempel, S.1    Buettner, G.2    O'Malley, Y.3    Wessels, D.4    Flaherty, D.5
  • 17
    • 0034816698 scopus 로고    scopus 로고
    • Cytochrome c is a potent catalyst of dichlorofluorescin oxidation: Implications for the role of reactive oxygen species in apoptosis
    • M. Burkitt, and P. Wardman 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
    • (2001) Biochem. Biophys. Res. Commun. , vol.282 , pp. 329-333
    • Burkitt, M.1    Wardman, P.2
  • 18
    • 0028369668 scopus 로고
    • Intracellular hydrogen peroxide and superoxide anion detection in endothelial cells
    • W. Carter, P. Narayanan, and J. Robinson Intracellular hydrogen peroxide and superoxide anion detection in endothelial cells J. Leukocyte Biol. 55 1994 253 258
    • (1994) J. Leukocyte Biol. , vol.55 , pp. 253-258
    • Carter, W.1    Narayanan, P.2    Robinson, J.3
  • 19
    • 0028108976 scopus 로고
    • Oxidation pathways for the intracellular probe 2′,7′- dichlorofluorescein
    • H. Zhu, G. Bannenberg, P. Moldeus, and H. Shertzer Oxidation pathways for the intracellular probe 2′,7′-dichlorofluorescein Arch. Toxicol. 68 1994 582 587
    • (1994) Arch. Toxicol. , vol.68 , pp. 582-587
    • Zhu, H.1    Bannenberg, G.2    Moldeus, P.3    Shertzer, H.4
  • 21
    • 0031423791 scopus 로고    scopus 로고
    • Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: Implications for intracellular measurement of reactive nitrogen and oxygen species
    • J. Crow Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: Implications for intracellular measurement of reactive nitrogen and oxygen species. Nitric Oxide 1 1997 145 157
    • (1997) Nitric Oxide , vol.1 , pp. 145-157
    • Crow, J.1
  • 22
    • 0035800823 scopus 로고    scopus 로고
    • Reaction of superoxide and nitric oxide with peroxynitrite: Implications for peroxynitrite-mediated oxidation reactions in vivo
    • D. Jourd'heuil, F. Jourd'heuil, P. Kutchukian, R. Musah, D. Wink, and M. Grisham Reaction of superoxide and nitric oxide with peroxynitrite: implications for peroxynitrite-mediated oxidation reactions in vivo J. Biol. Chem. 276 2001 28799 28805
    • (2001) J. Biol. Chem. , vol.276 , pp. 28799-28805
    • Jourd'Heuil, D.1    Jourd'Heuil, F.2    Kutchukian, P.3    Musah, R.4    Wink, D.5    Grisham, M.6
  • 23
    • 0042328260 scopus 로고    scopus 로고
    • Peroxynitrite-mediated oxidation of dichlorodihydrofluorescein and dihydrorhodamine
    • J. Glebska, and W. Koppenol Peroxynitrite-mediated oxidation of dichlorodihydrofluorescein and dihydrorhodamine Free Radic. Biol. Med. 35 2003 676 682
    • (2003) Free Radic. Biol. Med. , vol.35 , pp. 676-682
    • Glebska, J.1    Koppenol, W.2
  • 24
    • 0000126490 scopus 로고
    • + from hydrogen peroxide formation in pulse-irradiated oxygenated water
    • + from hydrogen peroxide formation in pulse-irradiated oxygenated water J. Phys. Chem. 72 1968 626 631
    • (1968) J. Phys. Chem. , vol.72 , pp. 626-631
    • Sehested, K.1    Rasmussen, O.2    Fricke, H.3
  • 25
    • 0027428360 scopus 로고
    • Free radical intermediates in the oxidation of flavone-8-acetic acid: Possible involvement in its anti-tumour activity
    • L.P. Candeias, S.A. Everett, and P. Wardman Free radical intermediates in the oxidation of flavone-8-acetic acid: possible involvement in its anti-tumour activity Free Radic. Biol. Med. 15 1993 385 394
    • (1993) Free Radic. Biol. Med. , vol.15 , pp. 385-394
    • Candeias, L.P.1    Everett, S.A.2    Wardman, P.3
  • 26
    • 37049084188 scopus 로고
    • Re-evaluation of thiocyanate dosimeter for pulse radiolysis
    • G. Buxton, and C. Stuart Re-evaluation of thiocyanate dosimeter for pulse radiolysis J. Chem. Soc. Faraday Trans. 91 1995 279 281
    • (1995) J. Chem. Soc. Faraday Trans. , vol.91 , pp. 279-281
    • Buxton, G.1    Stuart, C.2
  • 28
    • 0022516274 scopus 로고
    • Rate constant for reaction of hydroxyl radical with bicarbonate ions
    • G. Buxton, and A. Elliot Rate constant for reaction of hydroxyl radical with bicarbonate ions Radiat. Phys. Chem. 27 1986 241 243
    • (1986) Radiat. Phys. Chem. , vol.27 , pp. 241-243
    • Buxton, G.1    Elliot, A.2
  • 29
    • 0002627604 scopus 로고
    • Radiation chemistry of the liquid state. 1. Water and homogeneous aqueous solutions
    • J.F. R.M.A. VCH New York
    • G. Buxton Radiation chemistry of the liquid state. 1. Water and homogeneous aqueous solutions J.F. R.M.A. Radiation chemistry 1987 VCH New York 321 348
    • (1987) Radiation Chemistry , pp. 321-348
    • Buxton, G.1
  • 30
    • 0001129581 scopus 로고
    • Carbonate radical in flash photolysis and pulse radiolysis of aqueous carbonate solutions
    • D. Behar, G. Czapski, and I. Duchovny Carbonate radical in flash photolysis and pulse radiolysis of aqueous carbonate solutions J. Phys. Chem. 74 1970 2206 2210
    • (1970) J. Phys. Chem. , vol.74 , pp. 2206-2210
    • Behar, D.1    Czapski, G.2    Duchovny, I.3
  • 32
    • 0002895368 scopus 로고    scopus 로고
    • Nitrogen dioxide in biology: Correlating chemical kinetics with biological effects
    • Z. Alfassi Wiley Chichester
    • P. Wardman Nitrogen dioxide in biology: correlating chemical kinetics with biological effects Z. Alfassi N-centered radicals 1998 Wiley Chichester 155 179
    • (1998) N-centered Radicals , pp. 155-179
    • Wardman, P.1
  • 33
    • 0001623767 scopus 로고
    • Pulse radiolytische untersuchung einigerelementarprozesse der oxidation und reduktion des nitritions
    • M. Grätzel, A. Henglein, J. Lilie, and G. Beck Pulse radiolytische untersuchung einigerelementarprozesse der oxidation und reduktion des nitritions Ber. Bunsenges. Phys. Chem. 73 1969 646 653
    • (1969) Ber. Bunsenges. Phys. Chem. , vol.73 , pp. 646-653
    • Grätzel, M.1    Henglein, A.2    Lilie, J.3    Beck, G.4
  • 34
    • 0021006899 scopus 로고
    • Kinetics of reactive dissolution of nitrogen oxide in aqueous solutions
    • S. Schwartz, and W. White Kinetics of reactive dissolution of nitrogen oxide in aqueous solutions Adv. Environ. Sci. Technol. 12 1983 1 116
    • (1983) Adv. Environ. Sci. Technol. , vol.12 , pp. 1-116
    • Schwartz, S.1    White, W.2
  • 37
    • 0016425962 scopus 로고
    • The steady-state kinetics of peroxidase with 2,2′-azino-di-(3- ethylbenzthiazoline-6-sulphonic acid) as chromogen
    • R. Childs, W.G., and B. The steady-state kinetics of peroxidase with 2,2′-azino-di-(3-ethylbenzthiazoline-6-sulphonic acid) as chromogen Biochem. J. 145 1975 93 103
    • (1975) Biochem. J. , vol.145 , pp. 93-103
    • Childs, R.1    B, G.W.2
  • 38
    • 0037096198 scopus 로고    scopus 로고
    • Kinetics of the reaction of nitrogen dioxide with glutathione, cysteine and uric acid at physiological pH
    • E. Ford, M. Hughes, and P. Wardman Kinetics of the reaction of nitrogen dioxide with glutathione, cysteine and uric acid at physiological pH Free Radic. Biol. Med. 32 2002 1314 1323
    • (2002) Free Radic. Biol. Med. , vol.32 , pp. 1314-1323
    • Ford, E.1    Hughes, M.2    Wardman, P.3
  • 39
    • 0011160630 scopus 로고    scopus 로고
    • Measurement of rate constants for radical reaction in the liquid phase
    • Z.B. Alfassi John Wiley & Sons New York/Chichester
    • G. Buxton Measurement of rate constants for radical reaction in the liquid phase Z.B. Alfassi General aspects of the chemistry of radicals vol. 3 1999 John Wiley & Sons New York/Chichester 51 77
    • (1999) General Aspects of the Chemistry of Radicals , vol.3 , pp. 51-77
    • Buxton, G.1
  • 40
    • 0036569412 scopus 로고    scopus 로고
    • Nitrogen dioxide and carbonate radical anion: Two emerging radicals in biology
    • O. Augusto, M. Bonini, A. Amanso, and E. Linares Nitrogen dioxide and carbonate radical anion: two emerging radicals in biology Free Radic. Biol. Med. 32 2002 841 859
    • (2002) Free Radic. Biol. Med. , vol.32 , pp. 841-859
    • Augusto, O.1    Bonini, M.2    Amanso, A.3    Linares, E.4
  • 42
    • 0025166584 scopus 로고
    • Manganese(II) catalyzes the bicarbonate-dependent oxidation of amino acids by hydrogen peroxide and the amino acid-facilitated dismutation of hydrogen peroxide
    • B. Berlett, P. Chock, M.B., Y., and E. Stadtman Manganese(II) catalyzes the bicarbonate-dependent oxidation of amino acids by hydrogen peroxide and the amino acid-facilitated dismutation of hydrogen peroxide Proc. Natl. Acad. Sci. USA 87 1990 389 393
    • (1990) Proc. Natl. Acad. Sci. USA , vol.87 , pp. 389-393
    • Berlett, B.1    Chock, P.2    Y, M.B.3    Stadtman, E.4
  • 43
    • 0027413240 scopus 로고
    • Peroxynitrite-induced luminol chemiluminescence
    • R. Radi, T. Cosgrove, J. Beckman, and B. Freeman Peroxynitrite-induced luminol chemiluminescence Biochem. J. 290 1993 51 57
    • (1993) Biochem. J. , vol.290 , pp. 51-57
    • Radi, R.1    Cosgrove, T.2    Beckman, J.3    Freeman, B.4
  • 44
    • 0029112912 scopus 로고
    • Role of compartmentation in promoting toxicity of leukocyte-generated strong oxidants
    • S. Lymar, and J. Hurst Role of compartmentation in promoting toxicity of leukocyte-generated strong oxidants Chem. Res. Toxicol. 8 1995 833 840
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 833-840
    • Lymar, S.1    Hurst, J.2
  • 45
    • 0034640515 scopus 로고    scopus 로고
    • Bicarbonate enhances the hydroxylation, nitration, and peroxidation reactions catalyzed by copper, zinc superoxide dismutase: Intermediacy of carbonate anion radical
    • H. Zhang, J. Joseph, C. Felix, and B. Kalyanaraman Bicarbonate enhances the hydroxylation, nitration, and peroxidation reactions catalyzed by copper, zinc superoxide dismutase: intermediacy of carbonate anion radical J. Biol. Chem. 275 2000 14038 14045
    • (2000) J. Biol. Chem. , vol.275 , pp. 14038-14045
    • Zhang, H.1    Joseph, J.2    Felix, C.3    Kalyanaraman, B.4
  • 47
    • 0032830132 scopus 로고    scopus 로고
    • 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
    • C. Rota, C. Chignell, and R. Mason 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 878 881
    • (1999) Free Radic. Biol. Med. , vol.27 , pp. 878-881
    • Rota, C.1    Chignell, C.2    Mason, R.3
  • 48
    • 0033214972 scopus 로고    scopus 로고
    • Phenoxyl free radical formation during the oxidation of the fluorescent dye 2′,7′-dichlorofluorescein by horseradish peroxidase: Possible consequences for oxidative stress measurements
    • C. Rota, Y. Fann, and R. Mason Phenoxyl free radical formation during the oxidation of the fluorescent dye 2′,7′-dichlorofluorescein by horseradish peroxidase: possible consequences for oxidative stress measurements J. Biol. Chem. 274 1999 28161 28168
    • (1999) J. Biol. Chem. , vol.274 , pp. 28161-28168
    • Rota, C.1    Fann, Y.2    Mason, R.3
  • 49
    • 0344076349 scopus 로고    scopus 로고
    • Photoreduction of the fluorescent dye 2′-7′- dichlorofluorescein: A spin trapping and direct electron spin resonance study with implications for oxidative stress measurements
    • E. Marchesi, C. Rota, Y. Fann, C. Chignell, and R. Mason 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
    • (1999) Free Radic. Biol. Med. , vol.26 , pp. 148-161
    • Marchesi, E.1    Rota, C.2    Fann, Y.3    Chignell, C.4    Mason, R.5
  • 50
    • 0037446363 scopus 로고    scopus 로고
    • A photochemical study of cells loaded with 2′,7′- dichlorofluorescin: Implication for the detection of reactive oxygen species generated during UVA irradiation
    • C. Chignell, and R. Sik A photochemical study of cells loaded with 2′,7′-dichlorofluorescin: implication for the detection of reactive oxygen species generated during UVA irradiation Free Radic. Biol. Med. 34 2003 1029 1034
    • (2003) Free Radic. Biol. Med. , vol.34 , pp. 1029-1034
    • Chignell, C.1    Sik, R.2


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