Methods for detection of reactive metabolites of oxygen and nitrogen: In vitro and in vivo considerations

American Journal of Physiology - Regulatory Integrative and Comparative Physiology

Volumn 286, Issue 3 55-3, 2004, Pages

  Tarpey, Margaret M ^a,b   Wink, David A ^c   Grisham, Matthew B ^d  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^b UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

^d LOUISIANA STATE UNIVERSITY HEALTH SCIENCES CENTER   (United States)

Author keywords

Free radical; Hydrogen peroxide; Nitric oxide; Peroxynitrite; Superoxide

Indexed keywords

3 NITROTYROSINE; 3-NITROTYROSINE; DRUG DERIVATIVE; HYDROGEN PEROXIDE; NITRIC OXIDE; NITROGEN; OXIDIZING AGENT; OXYGEN; PEROXYNITROUS ACID; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; S NITROSOTHIOL; SUPEROXIDE; TYROSINE; UNCLASSIFIED DRUG;

ALGORITHM; ANALYTIC METHOD; ANIMAL; CATABOLISM; CHEMICAL ANALYSIS; DECOMPOSITION; ENZYME MECHANISM; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LIPID PEROXIDATION; METABOLISM; METABOLITE; OXIDATIVE STRESS; PHYSIOLOGY; PRIORITY JOURNAL; REVIEW;

EID: 1342289237     PISSN: 03636119     EISSN: None     Source Type: Journal    
DOI: 10.1152/ajpregu.00361.2003     Document Type: Review

References (147)

1. Abrahamsson T, Brandt U, Marklund SL, and Sjoqvist PO. Vascular bound recombinant extracellular superoxide dismutase type C protects against the detrimental effects of superoxide radicals on endothelium-dependent arterial relaxation. Circ Res 70: 264-271, 1992.
2. - donation by S-nitrosothiols: implications for regulation of physiological functions by S-nitrosylation and acceleration of disulfide formation. Arch Biochem Biophys 318: 279-285, 1995.
3. Azzi A, Montecucco C, and Richter C. The use of acetylated ferricytochrome c for the detection of superoxide radicals produced in biological membranes. Biochem Biophys Res Commun 65: 597-603, 1975.
4. Ballou D, Palmer G, and Massey V. Direct demonstration of superoxide anion production during the oxidation of reduced flavin and of its catalytic decomposition by erythrocuprein. Biochem Biophys Res Commun 36: 898-904, 1969.
5. Barbacanne MA, Souchard JP, Darblade B, Iliou JP, Nepveu F, Pipy B, Bayard F, and Arnal JF. Detection of superoxide anion released extracellularly by endothelial cells using cytochrome c reduction, ESR, fluorescence and lucigenin-enhanced chemiluminescence techniques. Free Radic Biol Med 29: 388-396, 2000.
6. Bass DA, Parce JW, Dechatelet LR, Szejda P, Seeds MC, and Thomas M. Flow cytometric studies of oxidative product formation by neutrophils: a graded response to membrane stimulation. J Immunol 130: 1910-1917, 1983.
7. Beckman JS and Koppenol WH. Nitric oxide superoxide and peroxynitrite: the good, the bad, and ugly. Am J Physiol Cell Physiol 271: C1424-C1437, 1996.
8. Benov L, Sztejnberg L, and Fridovich I. Critical evaluation of the use of hydroethidine as a measure of superoxide anion radical. Free Radic Biol Med 25: 826-831, 1998.
9. Bindokas VP, Jordan J, Lee CC, and Miller RJ. Superoxide production in rat hippocampal neurons: selective imaging with hydroethidine. J Neurosci 16: 1324-1336, 1996.
10. Borbat PP, Costa-Filho AJ, Earle KA, Moscicki JK, and Freed JH. Electron spin resonance in studies of membranes and proteins. Science 291: 266-269, 2001.
11. Boveris A. Determination of the production of superoxide radicals and hydrogen peroxide in mitochondria. Methods Enzymol 105: 429-435, 1984.
12. Boveris A, Martino E, and Stoppani AO. Evaluation of the horseradish peroxidase-scopoletin method for the measurement of hydrogen peroxide formation in biological systems. Anal Biochem 80: 145-158, 1977.
13. Brawn K and Fridovich I. Superoxide radical and superoxide dismutases: threat and defense. Acta Physiol Scand 492: 9-18, 1980.
14. Brennan ML, Wu W, Fu X, Shen Z, Song W, Frost H, Vadseth C, Narine L, Lenkiewicz E, Borchers MT, Lusis AJ, Lee JJ, Lee NA, Abu-Soud HM, Ischiropoulos H, and Hazen SL. A tale of two controversies: defining both the role of peroxidases in nitrotyrosine formation in vivo using eosinophil peroxidase and myeloperoxidase-deficient mice, and the nature of peroxidase-generated reactive nitrogen species. J Biol Chem 277: 17415-17427, 2002.
15. Budd SL, Castilho RF, and Nicholls DG. Mitochondrial membrane potential and hydroethidine-monitored superoxide generation in cultured cerebellar granule cells. FEBS Lett 415: 21-24, 1997.
16. Burkitt MJ 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: 329-333, 2001.
17. Cai J, Yang J, and Jones DP. Mitochondrial control of apoptosis: the role of cytochrome c. Biochim Biophys Acta 1366: 139-149, 1998.
18. Carter WO, Narayanan PK, and Robinson JP. Intracellular hydrogen peroxide and superoxide anion detection in endothelial cells. J Leukoc Biol 55: 253-258, 1994.
19. Castro L, Rodriguez M, and Radi R. Aconitase is readily inactivated by peroxynitrite, but not by its precursor, nitric oxide. J Biol Chem 269: 29409-29415, 1994.
20. Cathcart R, Schwiers E, and Ames BN. Detection of picomole levels of hydroperoxides using a fluorescent dichlorofluorescein assay. Anal Biochem 134: 111-116, 1983.
21. Cohen G, Kim M, and Ogwu V. A modified catalase assay suitable for a plate reader and for the analysis of brain cell cultures. J Neurosci Methods 67: 53-56, 1996.
22. Crow JP. Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: implications for intracellular measurement of reactive nitrogen and oxygen species. Nitric Oxide 1: 145-157, 1997.
23. Dambrova M, Baumane L, Kalvinsh I, and Wikberg JE. Improved method for EPR detection of DEPMPO-superoxide radicals by liquid nitrogen freezing. Biochem Biophys Res Commun 275: 895-898, 2000.
24. Dikalov S, Skatchkov M, and Bassenge E. Spin trapping of superoxide radicals and peroxynitrite by 1-hydroxy-3-carboxy-pyrrolidine and 1-hydroxy-2,2,6,6-tetramethyl-4-oxo-piperidine and the stability of corresponding nitroxyl radicals towards biological reductants. Biochem Biophys Res Commun 231: 701-704, 1997.
25. Duerrschmidt N, Wippich N, Goettsch W, Broemme HJ, and Morawietz H. Endothelin-1 induces NAD(P)H oxidase in human endothelial cells. Biochem Biophys Res Commun 269: 713-717, 2000.
26. Eiserich JP, Baldus S, Brennan ML, Ma W, Zhang C, Tousson A, Castro L, Lusis AJ, Nauseef WM, White CR, and Freeman BA. Myeloperoxidase, a leukocyte-derived vascular NO oxidase. Science 296: 2391-2394, 2002.
27. Eiserich JP, Cross CE, Jones AD, Halliwell B, and van der Vliet A. Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric oxide-mediated protein modification. J Biol Chem 271: 19199-19208, 1996.
28. Eiserich JP, Hristova M, Cross CE, Jones AD, Freeman BA, Halliwell B, and van der Vliet A. Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391: 393-397, 1998.
29. Espey MG, Miranda KM, Thomas DD, and Wink DA. Distinction between nitrosating mechanisms within human cells and aqueous solution. J Biol Chem 276: 30085-30091, 2001.
30. Espey MG, Miranda KM, Thomas DD, and Wink DA. Ingress and reactive chemistry of nitroxyl-derived species within human cells. Free Radic Biol Med 33: 827-834, 2002.
31. Espey MG, Thomas DD, Miranda KM, and Wink DA. Focusing of nitric oxide mediated nitrosation and oxidative nitrosylation as a consequence of reaction with superoxide. Proc Natl Acad Sci USA 99: 11127-11132, 2002.
32. Flint DH, Tuminello JF, and Emptage MH. The inactivation of Fe-S cluster containing hydro-lyases by superoxide. J Biol Chem 268: 22369-22376, 1993.
33. Frejaville C, Karoui H, Tuccio B, Le Moigne F, Culcasi M, Pietri S, Lauricella R, and Tordo P. 5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide: a new efficient phosphorylated nitrone for the in vitro and in vivo spin trapping of oxygen-centered radicals. J Med Chem 38: 258-265, 1995.
34. Fridovich I. Cytochrome c. In: Handbook of Methods for Oxygen Radical Research, edited by Greenwald RA. Boca Raton, FL: CRC, 1985, p. 121-122.
35. Fujii H and Berliner LJ. Nitric oxide: prospects and perspectives of in vivo detection by L-band EPR spectroscopy. Phys Med Biol 43: 1949-1956, 1998.
36. Gardner PR and Fridovich I. Inactivation-reactivation of aconitase in Escherichia coli. A sensitive measure of superoxide radical. J Biol Chem 267: 8757-8763, 1992.
37. Gardner PR, Nguyen DD, and White CW. Superoxide scavenging by Mn(II/III) tetrakis (1-methyl-4-pyridyl) porphyrin in mammalian cells. Arch Biochem Biophys 325: 20-28, 1996.
38. Gardner PR, Raineri I, Epstein LB, and White CW. Superoxide radical and iron modulate aconitase activity in mammalian cells. J Biol Chem 270: 13399-13405, 1995.
39. Goto T, Inoue S, Sugiura S, Nishikawa K, Isobe M, and Abe Y. Cypridina bioluminescence V structure of emitting species in the luminescence of Cypridina luciferin and its related compounds. Tetrahedron Lett 37: 4035-4038, 1968.
40. Gow AJ and Stamler JS. Reactions between nitric oxide and haemoglobin under physiological conditions. Nature 391: 169-173, 1998.
41. Granger DL, Taintor RR, Boockvar KS, and Hibbs JB Jr. Measurement of nitrate and nitrite in biological samples using nitrate reductase and Griess reaction. Methods Enzymol 268: 142-151, 1996.
42. Green DR and Reed JC. Mitochondria and apoptosis. Science 281: 1309-1312, 1998.
43. Grisham MB. Oxidants and free radicals in inflammatory bowel disease. Lancet 344: 859-861, 1994.
44. Grisham MB, Johnson GG, and Lancaster JR Jr. Quantitation of nitrate and nitrite in extracellular fluids. Methods Enzymol 268: 237-246, 1996.
45. 2 generation by rat kidney in glycerol-induced renal failure. Am J Physiol Renal Fluid Electrolyte Physiol 257: F440-F445, 1989.
46. Halliwell B. How to characterize an antioxidant: an update. Biochem Soc Symp 61: 73-101, 1995.
47. Halliwell B and Gutteridge JMC. Detection of free radicals and other reactive species: trapping and finger printing. In: Free Radicals in Biology and Medicine, edited by Halliwell B and Gutteridge JMC. Oxford, UK: Oxford Press, 2000, p. 351-429.
48. Hausladen A and Fridovich I. Superoxide and peroxynitrite inactivate aconitases, but nitric oxide does not. J Biol Chem 269: 29405-29408, 1994.
49. Hausladen A and Fridovich I. Measuring nitric oxide and superoxide: rate constants for aconitase reactivity. Methods Enzymol 269: 37-41, 1996.
50. He G, Samouilov A, Kuppusamy P, and Zweier JL. In vivo imaging of free radicals: applications from mouse to man. Mol Cell Biochem 234-235: 359-367, 2002.
51. Hink U, Li H, Mollnau H, Oelze M, Matheis E, Hartmann M, Skatchkov M, Thaiss F, Stahl RA, Warnholtz A, Meinertz T, Griendling K, Harrison DG, Forstermann U, and Munzel T. Mechanisms underlying endothelial dysfunction in diabetes mellitus. Circ Res 88: E14-E22, 2001.
52. Hinkle PC, Butow RA, Racker E, and Chance B. Partial resolution of the enzymes catalyzing oxidative phosphorylation. XV Reverse electron transfer in the flavin-cytochrome beta region of the respiratory chain of beef heart submitochondrial particles. J Biol Chem 242: 5169-5173, 1967.
53. Huang X, Frenkel K, Klein CB, and Costa M. Nickel induces increased oxidants in intact cultured mammalian cells as detected by dichlorofluorescein fluorescence. Toxicol Appl Pharmacol 120: 29-36, 1993.
54. Hyslop PA and Sklar LA. A quantitative fluorimetric assay for the determination of oxidant production by polymorphonuclear leukocytes: its use in the simultaneous fluorimetric assay of cellular activation processes. Anal Biochem 141: 280-286, 1984.
55. Ignarro LJ. Nitric oxide as a unique signaling molecule in the vascular system: a historical overview. J Physiol Pharmacol 53: 503-514, 2002.
56. Ignarro LJ, Fukuto JM, Griscavage JM, Rogers NE, and Byrns RE. Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate: comparison with enzymatically formed nitric oxide from L-arginine. Proc Natl Acad Sci USA 90: 8103-8107, 1993.
57. Ishii M, Shimizu S, Yamamoto T, Momose K, and Kuroiwa Y. Acceleration of oxidative stress-induced endothelial cell death by nitric oxide synthase dysfunction accompanied with decrease in tetrahydrobiopterin content. Life Sci 61: 739-747, 1997.
58. Janiszewski M, Souza HP, Liu X, Pedro MA, Zweier JL, and Laurindo FR. Overestimation of NADH-driven vascular oxidase activity due to lucigenin artifacts. Free Radic Biol Med 32: 446-453, 2002.
59. Jia L, Bonaventura C, Bonaventura J, and Stamler JS. S-nitrosohaemoglobin: a dynamic activity of blood involved in vascular control. Nature 380: 221-226, 1996.
60. Jones DP. Redox potential of GSH/GSSG couple: assay and biological significance. Methods Enzymol 348: 93-112, 2002.
61. Jourd'heuil D, Gray L, and Grisham MB. S-nitrosothiol formation in blood of lipopolysaccharide-treated rats. Biochem Biophys Res Commun 273: 22-26, 2000.
62. Jourd'heuil D, Hallen K, Feelisch M, and Grisham MB. Dynamic state of S-nitrosothiols in human plasma and whole blood. Free Radic Biol Med 28: 409-417, 2000.
63. Keston AS and Brandt R. The fluorometric analysis of ultramicro quantities of hydrogen peroxide. Anal Biochem 11: 1-5, 1965.
64. Kilinc K, Kilinc A, Wolf RE, and Grisham MB. Myoglobin-catalyzed tyrosine nitration: no need for peroxynitrite. Biochem Biophys Res Commun 285: 273-276, 2001.
65. Kinnula VL, Mirza Z, Crapo JD, and Whorton AR. Modulation of hydrogen peroxide release from vascular endothelial cells by oxygen. Am J Respir Cell Mol Biol 9: 603-609, 1993.
66. Kojima H, Hirotani M, Nakatsubo N, Kikuchi K, Urano Y, Higuchi T, Hirata Y, and Nagano T. Bioimaging of nitric oxide with fluorescent indicators based on the rhodamine chromophore. Anal Chem 73: 1967-1973, 2001.
67. Kojima H, Nakatsubo N, Kikuchi K, Kawahara S, Kirino Y, Nagoshi H, Hirata Y, and Nagano T. Detection and imaging of nitric oxide with novel fluorescent indicators: diaminofluoresceins. Anal Chem 70: 2446-2453, 1998.
68. Kooy NW, Royall JA, and Ischiropoulos H. Oxidation of 2′,7′-dichlorofluorescin by peroxynitrite. Free Radic Res 27: 245-254, 1997.
69. Kuthan H, Ullrich V, and Estabrook RW. A quantitative test for superoxide radicals produced in biological systems. Biochem J 203: 551-558, 1982.
70. Land EJ and Swallow AJ. One-electron reactions in biochemical systems as studied by pulse radiolysis. V. Cytochrome c. Arch Biochem Biophys 145: 365-372, 1971.
71. Landmesser U, Dikalov S, Price SR, McCann L, Fukai T, Holland SM, Mitch WE, and Harrison DG. Oxidation of tetrahydrobiopterin leads to uncoupling of endothelial cell nitric oxide synthase in hypertension. J Clin Invest 111: 1201-1209, 2003.
72. Larsen LN, Dahl E, and Bremer J. Peroxidative oxidation of leucodichlorofluorescein by prostaglandin H synthase in prostaglandin biosynthesis from polyunsaturated fatty acids. Biochim Biophys Acta 1299: 47-53, 1996.
73. Laurindo FR, Pedro MD Barbeiro HV, Pileggi F, Carvalho MH, Augusto O, and da Luz PL. Vascular free radical release ex vivo and in vivo evidence for a flow-dependent endothelial mechanism. Circ Res 74: 700-709, 1994.
74. LeBel CP, Ischiropoulos H, and Bondy SC. Evaluation of the probe 2′,7′-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem Res Toxicol 5: 227-231, 1992.
75. Liochev SI and Fridovich I. Lucigenin (bis-N-methylacridinium) as a mediator of superoxide anion production. Arch Biochem Biophys 337: 115-120, 1997.
76. Liu X, Miller MJ, Joshi MS, Thomas DD, and Lancaster JR Jr. Accelerated reaction of nitric oxide with 02 within the hydrophobic interior of biological membranes. Proc Natl Acad Sci USA 95: 2175-2179, 1998.
77. Lucas M and Solano F. Coelenterazine is a superoxide anion-sensitive chemiluminescent probe: its usefulness in the assay of respiratory burst in neutrophils. Anal Biochem 206: 273-277, 1992.
78. Lynch RE and Fridovich I. Permeation of the erythrocyte stroma by superoxide radical. J Biol Chem 253: 4697-4699, 1978.
79. Makino K, Hagiwara T, Hagi A, Nishi M, and Murakami A. Cautionary note for DMPO spin trapping in the presence of iron ion. Biochem Biophys Res Commun 172: 1073-1080, 1990.
80. Margoliash E, Novogrodsky A, and Schejter A. Irreversible reaction of 3-amino 1:2,4-triazole and related inhibitors with the protein catalase. Biochem J 74: 339-348, 1960.
81. Marklund SL and Karlsson K. Extracellular-superoxide dismutase, distribution in the body and therapeutic applications. Adv Exp Med Biol 264: 1-4, 1990.
82. Massey V. The microestimation of succinate and the extinction coefficient of cytochrome c. Biochim Biophys Acta 34: 255-256, 1959.
83. McCord JM and Fridovich I. The reduction of cytochrome c by milk xanthine oxidase. J Biol Chem 243: 5753-5760, 1968.
84. McCord JM and Fridovich I. The utility of superoxide dismutase in studying free radical reactions. I. Radicals generated by the interaction of sulfite, dimethyl sulfoxide, and oxygen. J Biol Chem 244: 6056-6063, 1969.
85. Melov S, Coskun P, Patel M, Tuinstra R, Cottrell B, Jun AS, Zastawny TH, Dizdaroglu M, Goodman SI, Huang TT, Miziorko H, Epstein CJ, and Wallace DC. Mitochondrial disease in superoxide dismutase 2 mutant mice. Proc Natl Acad Sci USA 96: 846-851, 1999.
86. Miles AM, Wink DA, Cook JC, and Grisham MB. Determination of nitric oxide using fluorescence spectroscopy. Methods Enzymol 268: 105-120, 1996.
87. Miller FJ, Gutterman DD, Rios CD, Heistad DD, and Davidson BL. Superoxide production in vascular smooth muscle contributes to oxidative stress and impaired relaxation in atherosclerosis. Circ Res 82: 1298-1305, 1998.
88. Miranda KM, Yamada K, Espey MG, Thomas DD, DeGraff W, Mitchell JB, Krishna MC, Colton CA, and Wink DA. Further evidence for distinct reactive intermediates from nitroxyl and peroxynitrite: effects of buffer composition on the chemistry of Angeli's salt and synthetic peroxynitrite. Arch Biochem Biophys 401: 134-144, 2002.
89. Miranda KM, Espey MG, Yamada K, Krishna M, Ludwick N, Kim S, Jourd'heuil D, Grisham MB, Feelisch M, Fukuto JM, and Wink DA. Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion. J Biol Chem 276: 1720-1727, 2001.
90. Morrow JD, Hill KE, Burk RF, Nammour TM, Badr KF, and Roberts LJ. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc Natl Acad Sci USA 87: 9383-9387, 1990.
91. Munzel T, Afanas'ev IB, Kleschyov AL, and Harrison DG. Detection of superoxide in vascular tissue. Arterioscler Thromb Vasc Biol 22: 1761-1768, 2002.
92. Nakano M. Assay for superoxide dismutase based on chemiluminescence of luciferin analog. Methods Enzymol 186: 227-232, 1990.
93. Nakano M. Determination of superoxide radical and singlet oxygen based on chemiluminescence of luciferin analogs. Methods Enzymol 186: 585-591, 1990.
94. Nakano M, Sugioka K, Ushijima Y, and Goto T. Chemiluminescence probe with Cypridina luciferin analog, 2-methyl-6-phenyl-3,7-dihydroimidazo[1,2-a]pyrazin-3-one, for estimating the ability of human granulocytes to generate O2-. Anal Biochem 159: 363-369, 1986.
95. O'Brien PJ. Superoxide production. Methods Enzymol 105: 370-378, 1984.
96. 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: 21-27, 2002.
97. Ohshima H, Celan I, Chazotte L, Pignatelli B, and Mower HF. Analysis of 3-nitrotyrosine in biological fluids and protein hydrolyzates by high-performance liquid chromatography using a postseparation, online reduction column and electrochemical detection: results with various nitrating agents. Nitric Oxide 3: 132-141, 1999.
98. Paler-Martinez A, Panus PC, Chumley PH, Ryan U, Hardy MM, and Freeman BA. Endogenous xanthine oxidase does not significantly contribute to vascular endothelial production of reactive oxygen species. Arch Biochem Biophys 311: 79-85, 1994.
99. Patel M, Day BJ, Crapo JD, Fridovich I, and McNamara JO. Requirement for superoxide in excitotoxic cell death. Neuron 16: 345-355, 1996.
100. Paul B and Sbarra AJ. The role of the phagocyte in host-parasite interactions. 13. The direct quantitative estimation of H202 in phagocytizing cells. Biochim Biophys Acta 156: 168-178, 1968.
101. Pfeiffer S, Gorren AC, Schmidt K, Werner ER, Hansert B, Bohle DS, and Mayer B. Metabolic fate of peroxynitrite in aqueous solution. Reaction with nitric oxide and pH-dependent decomposition to nitrite and oxygen in a 2:1 stoichiometry. J Biol Chem 272: 3465-3470, 1997.
102. Piantadosi CA and Tatro LG. Regional H202 concentration in rat brain after hyperoxic convulsions. J Appl Physiol 69: 1761-1766, 1990.
103. Pick E and Keisari Y. A simple colorimetric method for the measurement of hydrogen peroxide produced by cells in culture. J Immunol Methods 38: 161-170, 1980.
104. Prutz WA, Monig H, Butler J, and Land EJ. Reactions of nitrogen dioxide in aqueous model systems: oxidation of tyrosine units in peptides and proteins. Arch Biochem Biophys 243: 125-134, 1985.
105. Pryor WA, Stanley JP, and Blair E. Autoxidation of polyunsaturated fatty acids: II. A suggested mechanism for the formation of TBA-reactive materials from prostaglandin-like endoperoxides. Lipids 11: 370-379, 1976.
106. Quaresima V and Ferrari M. Current status of electron spin resonance (ESR) for in vivo detection of free radicals. Phys Med Biol 43: 1937-1947, 1998.
107. Raha S, McEachern GE, Myint AT, and Robinson BH. Superoxides from mitochondrial complex III: the role of manganese superoxide dismutase. Free Radic Biol Med 29: 170-180, 2000.
108. Rice-Evans CA and Diplock AT. Current status of antioxidant therapy. Free Radic Biol Med 15: 77-96, 1993.
109. Roberts LJ and Morrow JD. Measurement of F(2)-isoprostanes as an index of oxidative stress in vivo. Free Radic Biol Med 28: 505-513, 2000.
110. Rosen GM and Freeman BA. Detection of superoxide generated by endothelial cells. Proc Natl Acad Sci USA 81: 7269-7273, 1984.
111. Rota C, Chignell CF, and Mason RP. 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: 873-881, 1999.
112. Rota C, Fann YC, and Mason RP. 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: 28161-28168, 1999.
113. Rothe G and Valet G. Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,7′ -dichlorofluorescin. J Leukoc Biol 47: 440-448, 1990.
114. Roubaud V, Sankarapandi S, Kuppusamy P, Tordo P, and Zweier JL. Quantitative measurement of superoxide generation using the spin trap 5-(diethoxyphosphoryl)-5-methyl-l-pyrroline-N-oxide. Anal Biochem 247: 404-411, 1997.
115. Royall JA and Ischiropoulos H. Evaluation of 2′,7′ -dichlorofluorescin and dihydrorhodamine 123 as fluorescent probes for intracellular H202 in cultured endothelial cells. Arch Biochem Biophys 302: 348-355, 1993.
116. 2 production by macrophages and neutrophils with homovanillic acid and horse-radish peroxidase. J Immunol Methods 63: 347-357, 1983.
117. Saitoh D, Kadota T, Okada Y, Masuda Y, Ohno H, and Inoue M. Direct evidence for the occurrence of superoxide radicals in the small intestine of the burned rat. Am J Emerg Med 13: 37-40, 1995.
118. Senft AP, Dalton TP, Nebert DW, Genter MB, Hutchinson RJ, and Shertzer HG. Dioxin increases reactive oxygen production in mouse liver mitochondria. Toxicol Appl Pharmacol 178: 15-21, 2002.
119. Shimomura O and Johnson FH. Peroxidized coelenterazine, the active group in the photoprotein aequorin. Proc Natl Acad Sci USA 75: 2611-2615, 1978.
120. Skatchkov MP, Sperling D, Hink U, Anggard E, and Munzel T. Quantification of superoxide radical formation in intact vascular tissue using a Cypridina luciferin analog as an alternative to lucigenin. Biochem Biophys Res Commun 248: 382-386, 1998.
121. Skatchkov MP, Sperling D, Hink U, Mulsch A, Harrison DG, Sindermann I, Meinertz T, and Munzel T. Validation of lucigenin as a chemiluminescent probe to monitor vascular superoxide as well as basal vascular nitric oxide production. Biochem Biophys Res Commun 254: 319-324, 1999.
122. Skulachev VP. Membrane-linked systems preventing superoxide formation. Biosci Rep 17: 347-366, 1997.
123. Sorescu D, Weiss D, Lassegue B, Clempus RE, Szocs K, Sorescu GP, Valppu L, Quinn MT, Lambeth JD, Vega JD, Taylor WR, and Griendling KK. Superoxide production and expression of nox family proteins in human atherosclerosis. Circulation 105: 1429-1435, 2002.
124. Souza HP, Souza LC, Anastacio VM, Pereira AC, Junqueira ML, Krieger JE, da Luz PL, Augusto O, and Laurindo FR. Vascular oxidant stress early after balloon injury: evidence for increased NAD(P)H oxidoreductase activity. Free Radic Biol Med 28: 1232-1242, 2000.
125. Stamler JS. S-nitrosothiols and the bioregulatory actions of nitrogen oxides through reactions with thiol groups. Curr Top Microbiol Immunol 196: 19-36, 1995.
126. Stamler JS, Simon DI, Osborne JA, Mullins ME, Jaraki O, Michel T, Singel DJ, and Loscalzo J. S-nitrosylation of proteins with nitric oxide: synthesis and characterization of biologically active compounds. Proc Natl Acad Sci USA 89: 444-448, 1992.
127. Staniek K and Nohl H. H(2)O(2) detection from intact mitochondria as a measure for one-electron reduction of dioxygen requires a non-invasive assay system. Biochim Biophys Acta 1413: 70-80, 1999.
128. Sugioka K, Nakano M, Kurashige S, Akuzawa Y, and Goto T. A chemiluminescent probe with a Cypridina luciferin analog, 2-methyl-6-phenyl-3,7-dihydroimidazo[1,2-a]pyrazin-3-one, specific and sensitive for O2- production in phago@ytizing macrophages. FEBS Lett 197: 27-30, 1986.
129. Suzuki H, Swei A, Zweifach BW, and Schmid-Schonbein GW. In vivo evidence for microvascular oxidative stress in spontaneously hypertensive rats Hydroethidine microfluorography. Hypertension 25: 1083-1089, 1995.
130. Takahashi A, Nakano M, Mashiko S, and Inaba H. The first observation of O2- generation in in situ lungs of rats treated with drugs to induce experimental acute respiratory distress syndrome. FEBS Lett 261: 369-372, 1990.
131. Tampo Y, Kotamraju S, Chitambar CR, Kalivendi SV, Keszler A, Joseph J, and Kalyanaraman B. Oxidative stress-induced iron signaling is responsible for peroxide-dependent oxidation of dichlorodihydrofluorescein in endothelial cells: role of transferrin receptor-dependent iron uptake in apoptosis. Circ Res 92: 56-63, 2003.
132. Tanaka M, Sotomatsu A, Yoshida T, Hirai S, and Nishida A. Detection of superoxide production by activated microglia using a sensitive and specific chemiluminescence assay and microglia-mediated PC12h cell death. J Neurochem 63: 266-270, 1994.
133. Tarpey MM and Fridovich I. Methods of detection of vascular reactive species: nitric oxide, superoxide, hydrogen peroxide, and peroxynitrite. Circ Res 89: 224-236, 2001.
134. Tarpey MM, White CR, Suarez E, Richardson G, Radi R, and Freeman BA. Chemiluminescent detection of oxidants in vascular tissue: lucigenin but not coelenterazine enhances superoxide formation. Circ Res 84: 1203-1211, 1999.
135. Teranishi K and Shimomura O. Coelenterazine analogs as chemiluminescent probe for superoxide anion. Anal Biochem 249: 37-43, 1997.
136. Thomas DD, Espey MG, Vitek MP, Miranda KM, and Wink DA. Protein nitration is mediated by heme and free metals through Fenton-type chemistry: an alternative to the NO/O2- reaction. Proc Natl Acad Sci USA 99: 12691-12696, 2002.
137. Thomson L, Trujillo M, Telleri R, and Radi R. Kinetics of cytochrome c2+ oxidation by peroxynitrite: implications for superoxide measurements in nitric oxide-producing biological systems. Arch Biochem Biophys 319: 491-497, 1995.
138. Uehara K, Maruyama N, Huang CK, and Nakano M. The first application of a chemiluminescence probe, 2-methyl-6-[p-methoxyphenyl]-3,7-dihydroimidazo[1,2-a]pyrazin-3-one (MCLA), for detecting O2-production, in vitro, from Kupffer cells stimulated by phorbol myristate acetate. FEBS Lett 335: 167-170, 1993.
139. Ushiroda S, Maruyama Y, and Nakano M. Continuous detection of superoxide in situ during ischemia and reperfusion in the rabbit heart. Jpn Heart J 38: 91-105, 1997.
140. Vasquez-Vivar J, Hogg N, Pritchard KA Jr, Martasek P, and Kalyanaraman B. Superoxide anion formation from lucigenin: an electron spin resonance spin-trapping study. FEBS Lett 403: 127-130, 1997.
141. Vasquez-Vivar J, Kalyanaraman B, and Kennedy MC. Mitochondrial aconitase is a source of hydroxyl radical. An electron spin resonance investigation. J Biol Chem 275: 14064-14069, 2000.
142. Velan SS, Spencer RG, Zweier JL, and Kuppusamy P. Electron paramagnetic resonance oxygen mapping (EPROM): direct visualization of oxygen concentration in tissue. Magn Reson Med 43: 804-809, 2000.
143. Williams MD, Van Remmen H, Conrad CC, Huang TT, Epstein CJ, and Richardson A. Increased oxidative damage is correlated to altered mitochondrial function in heterozygous manganese superoxide dismutase knockout mice. J Biol Chem 273: 28510-28515, 1998.
144. Wink DA, Kim S, Coffin D, Cook JC, Vodovotz Y, Chistodoulou D, Jourd'heuil D, and Grisham MB. Detection of S-nitrosothiols by fluorometric and colorimetric methods. Methods Enzymol 301: 201-211, 1999.
145. Yusa T, Beckman JS, Crapo JD, and Freeman BA. Hyperoxia increases H202 production by brain in vivo. J Appl Physiol 63: 353-358, 1987.
146. Zhao H, Kalivendi SV, Joseph J, Zhang H, and Kalyanaraman B. Superoxide reacts with hydroethidine but forms a fluorescent product that is distinctly different from ethidium (Abstract). Free Radic Biol Med 33: S425, 2002.
147. Zhou M, Diwu Z, Panchuk-Voloshina N, and Haugland RP. A stable nonfluorescent derivative of resorufin for the fluorometric determination of trace hydrogen peroxide: applications in detecting the activity of phagocyte NADPH oxidase and other oxidases. Anal Biochem 253: 162-168, 1997.