The hydroxyl radical: From chemistry to human disease

Journal of Investigative Medicine

Volumn 44, Issue 6, 1996, Pages 324-346

  Lubec, Gert ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL RADICAL;

ANIMAL; CHEMISTRY; HUMAN; METABOLISM; REVIEW;

ANIMALS; HUMANS; HYDROXYL RADICAL;

EID: 0030210778     PISSN: 17088267     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (211)

1. Haber F, Weiss J. The catalytic decomposition of hydrogen peroxide by iron salts. Proceedings of the Royal of London: Mathematics and Physical Society 1934;147:332-51.
2. Walling C. Fenton's reagent revisited. J Am Chem Soc 1975;8:125-9.
3. Wink DA, Wink CB, Nims RW, Ford PC. Oxidizing intermediates generated in the Fenton reagent: kinetic arguments against the intermediacy of the hydroxy radical. Environm Health Perspect 1994;102:11-5.
4. Wink DA, Nims RW, Saavedra JE, Utermahlen WE, Ford PC. The Fenton oxidation mechanism: reactivities of biologically relevant substrates with two oxidizing intermediates differ from those predicted for the hydroxy radical. Proc Natl Acad Sci USA 1994;91:6604-8.
5. Khan AU, Kasha M. Singlet molecular oxygen in the Haber - Weiss reaction. Proc Natl Acad Sci USA 1994;91:12365-7.
6. 2 in aqueous solution. Direct evidence for the formation of the hydroxyl radical. Free Radic Res 1992;17:21-39.
7. Ueno S, Suglyama M, Susa N, Furukawa Y. Effect of dimethylthiourea on chromium VI-induced DNA single strand breaks in Chinese hamster V 79 cells. Mutat Res 1995;346:247-53.
8. Molyneux MJ, Davies MJ. Direct evidence for hydroxyl radical induced damage to nucleic acids by chromium (VI) derived species: implications for chromium carcinogenesis. Carcinogenesis 1995;16:875-82.
9. Gunther MR, Hanna PM, Mason RP, Cohen MS. Hydroxyl radical formation from cuprous ion and hydrogen peroxide: a spin trapping study. Arch Biochem Biophys 1995;316:515-22.
10. Van der Zee J, Krootjes BB, Chignell CF, Dubbelman TM. Hydroxyl radical generation by a light dependent Fenton reaction. Free Radic Biol Med 1993;14:105-13.
11. Hoigne J, Bader H. Ozonation of water: role of hydroxyl radicals as oxidising intermediates. Science 1975;190:782-4.
12. Byvoet P, Balis JU, Shelley SA, Montgomery MR, Barber MJ. Detection of hydroxyl radicals upon interaction of ozone with aqueous media or extracellular surfactant: the role of trace iron. Arch Biochem Biophys 1995;319:464-9.
13. Feix JB, Kalyanaraman B. Production of singlet oxygen-derived hydroxyl radical adducts during merocyanine 54o mediated photosensitization: analysis by ESR-spin trapping and HPLC with electrochemical detection. Arch Biochem Biophys 1991;291:43-51.
14. Doetsch PW, Zasatawny TH, Martin AM, Dizdaroglu M. Monomeric base damage products from adenine, guanine, thymine induced by exposure of DNA to ultraviolet radiation. Biochemistry 1995;34:737-42.
15. Masaki H, Atsumi T, Sakurai H. Detection of hydrogen peroxide and hydroxyl radicals in murine skin fibroblasts under UVB irradiation. Biochem Biophys Res Comm 1995;206:474-9.
16. Stadtman ER. Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal catalyzed reactions. Annu Rev Biochem 1993;62:797-821.
17. Getoff N. Pulse radiolysis of aromatic amino acids. State of the Art. Amino Acids 1992;2:195-214.
18. Premaratne S, Suehiro A, Suehiro GT, Araraki HY, McNamara JJ. Detection of hydroxyl free radicals in the reperfused primate heart. Free Radic Res 1994;21:19-25.
19. Onodera T, Ashraf M. Detection of hydroxyl radicals in the post-ischemic reperfused heart using salicylate as a trapping agent. J Mol Cell Cardiol 1991;23:365-70.
20. Tosaki A, Bagchi D, Pali T, Cordis GA, Das DK. Comparison of ESR and HPLC methods for the detection of .OH radicals in ischemic/reperfused hearts. A relationship between the genesis of free radicals and reperfusion arrhythmias. Biochem Pharmacol 1993;45:961-9.
21. Liu X, Tosaki A, Engelman RM, Das DK. Reduction of postischemic ventricular dysfunction and arrhythmias by trapping hydroxyl radicals with salicylic acid. Int J Tissue React 1993;15:25-30.
22. Sen S, Phillis JW. alpha-Phenyl-tert-butyl-nitrone attenuates hydroxyl radical production during ischemia-reperfusion injury of rat brain: and EPR study. Free Radic Res 1993;19:255-65.
23. Zhang J, Piantadosi CA. Prolonged production of hydroxyl radical in rat hippocampus after brain ischemia-reperfusion is decreased by 21-aminosteroids. Neurosci Lett 1994;177:127-30.
24. Martz D, Beer M, Betz AL. Dimethylthiourea reduces ischemic brain edema without affecting cerebral blood flow. J Cerebr Blood Flow Metab 1990;10:352-7.
25. Hall ED, Braughler JM. Free radicals in CNS injury. Res Publ Assoc Res Nerv Ment Dis 1993;71:81-105.
26. Hall ED, Andrus PK, Yonkers PA. Brain hydroxyl radical generation in acute experimental head injury. J Neurochem 1993;60:588-94.
27. Sen S, Goldman H, Morehead M, Murphy S, Phillis JW. Alpha-Phenyl-tertbutyl-nitrone inhibits free radical release in brain concussion. Free Radic Biol Med 1994;16:685-91.
28. Smith SL, Andrus PK, Zhang JR, Hall ED. Direct measurement of hydroxyl radicals, lipid peroxidation and blood brain barrier disruption following unilateral cortical impact head injury in the rat. J Neurotrauma 1994;11:393-404.
29. Lesnefsky EJ, Repine JE, Horwitz LD. Deferoxamine pretreatment reduces canine infarct size and oxidative injury. J Pharmacol Exp Ther 1990;253:1103-9.
30. Takemura G, Onodera T, Ashraf M. Characterization of exogenous hydroxyl radical effects on myocardial function, metabolism and ultrastructutre. J Mol Cell Cardiol 1994;26:441-54.
31. Taylor DE, Ghio AJ, Piantadosi CA. Reactive oxygen species produced by liver mitochondria of rats in sepsis. Arch Biochem Biophys 1995;316:70-6.
32. Partridge RS, Monroe SM, Parks JK, Johnson K, Parker WD, Eaton OR and Eaton SS. Spin trapping of azidyl and hydroxyl radicals in azide inhibited rat brain submitochondrial particles. Arch Biochem Biophys 1994;310:210-7.
33. Giulivi C, Boveris A, Cadenas E. Hydroxyl radical generation during mitochondrial electron transfer and the formation of 8-hydroxydesoxyguanosine in mitochondrial DNA. Arch Biochem Biophys 1995;316:909-16.
34. Kukielka E, Dicker E, Cederbaum Al. Increased production of reactive oxygen species by rat liver mitochondria after chronic ethanol treatment. Arch Biochem Biophys 1994;309:377-86.
35. Miller RA, Britigan E. The formation and biological significance of phagocyte-derived oxidants. J Investig Med 1995;43:39-49.
36. Rosen GM, Pou S, Ramos CL, Cohen MS, Britigan BE. Free radicals and phagocytic cells. FASEB J 1995;9:200-9.
37. Britigan BE, Coffman TJ, Buettner GR. Spin trapping evidence for the lack of significant hydroxyl radical production during the respiration burst of human phagocytes using a spin adduct resistant to superoxide mediated destruction. J Biol Chem 1990;265:2650-6.
38. Ramos CL, Pou S, Britigan BE, Cohen MS and Rosen GM. Spin trapping evidence for myeloperoxidase-dependent hydroxyl radical formation by human neutrophils and monocytes. J Biol Chem 1992;267:8307-12.
39. Pou S, Huang Yl, Bhan A, Bhadti VS, Hosmane RS, Wu SY, Cao GL, Rosen GM. A fluorophore-containing nitroxide as a probe to detect superoxide and hydroxyl radical generated by stimulated neutrophils. Anal Biochem 1993;212:85-90.
40. Fujimoto S, Kawakami N, Ohara A. Hydroxylation of phenylalanine and salicylate by stimulated polymorphonuclear leukocytes and the accelerating effect of glutathione on their hydroxylation. Biol Pharm Bull 1994;17:767-72.
41. McCormick ML, Roeder TL, Railsback MA, Britigan BE. Eosinophil peroxidase dependent hydroxyl radical generation by human eosinophils. J Biol Chem 1994;269:27914-9.
42. Ramos CL, Pou S, Rosen GM. Effect of anti-inflammatory drugs on myeloperoxidase-dependent hydroxyl radical generation by human neutrophils. Biochem Pharmacol 1995;49:1079-84.
43. Weiss SJ, Rustagi PK, LeBuglio AF. Human granulocyte generation of hydroxyl radical . J Exp Med 1978;147:316-23.
44. Sagone AL Jr, Wells RM, Democko C. Evidence that .OH production by human PMNs is related to prostaglandin metabolism. Inflammation 1980;4:65-71.
45. Candeias LP, Strafford MR, Wardman P. Formation of hydroxyl radicals on reaction of hypoichlorous acid with ferrocyanide, a model iron (II) complex. Free Radic Res 1994;20:241-9.
46. Beckman JS, Beckman TW, Chen J, Marshall PA, Freeman BA. Apparent hydroxyl radical production by peroxynitrite: implications for endothelial cell injury from nitric oxide and superoxide. Proc Natl Acad Sci USA 1990;87:1620-4.
47. Shi X, Lenhart A, Mao Y. ESR spin trapping investigation on peroxynitrite decomposition: no evidence for hydroxyl radical production. Biochem Biophys Res Comm 1994;203:1515-21.
48. Pou S, Nguyen SY, Gladwell T, Rosen GM. Does peroxynitrite generate hydroxyl radical? Biochim Biophys Acta 1995;1244:62-8.
49. Hunt JV, Wolff S. Oxidative glycation and free radical production: a causal mechanism of diabetic complications. Free Radic Res 1991;12:115-23.
50. Halllwell B, Gutteridge JMC. Free radicals in biology and medicine. Oxford: Clarendon Press, 1993.
51. Carubelli R, Schneider JE, Pye QN, Floyd RA. Cytotoxic effects of autooxidative glycation. Free Radic Biol Med 1995;18:265-9.
52. Hiramoto K, Kato T, Kikugawa K. Generation of DNA-breaking activity in the Maillard reaction of glucose-amino acid mixtures in a solid system. Mutat Res 1993;285:191-8.
53. Ohkuwa T, Sato Y, Naoi M. Hydroxyl radical formation in diabetic rats induced by streptozotocin. Life Sci 1995;56:1789-98.
54. Khaidar A, Marx M, Lubec B, Lubec G. L-arginine reduces heart collagen accumulation in the diabetic db/db mouse. Circulation 1994;90:479-83.
55. Lubec B, Hjelm M, Hoeger H, Gialamas J, Lubec G. 4-thiaproline reduces heart lipid peroxidation and collagen accumulation in the diabetic db/db mouse. Amino Acids. In press.
56. Ghiselli A, Laurenti O, De Mattia G, Maiani G, Ferro-Luzzi A. Salicylate hydroxylation as an early marker of in vivo oxidative stress in diabetic patients. Free Radic Biol Med 1992;13:621-6.
57. Iwahashi H, Parker CE, Mason RP, Tomer KB. Radical identification by liquid chromatography/thermospray mass spectrometry. Rapid Commun Mass Spectrom 1990;4:352-4.
58. Kadiiska MB, Hanna PM, Mason RP. In vivo ESR spin trapping evidence for hydroxyl radical mediated toxicity of paraquat and copper in rats. Toxicol Appl Pharmacol 1993;123:187-92.
59. Buettner GR, Mason RP. Spin-trapping methods for detecting superoxide and hydroxyl free radicals in vitro and in vivo. Methods Enzymol 1990;186:127-33.
60. Halpern HJ, Yu C, Barth E, Peric M, Rosen GM. In situ detection, by spin trapping, of hydroxyl radical markers produced from ionizing radiation in the tumour of a living mouse. Proc Natl Acad Sci USA 1995;92:796-800.
61. Burkitt MJ. ESR spin trapping studies into the nature of the oxidizing species formed in the Fenton reaction: pitfalls associated with the use of 5,5-dimethyl-lpyrroline-N-oxide in the detection of the hydroxyl radical. Free Radic Res 1993;18:43-57.
62. 2 gas chromatography isotope ratio mass spectrometry. Anal Biochem 1994;220:129-36.
63. Naughton DP, Grootveld M, Blake DR, Guestrin HR, Narayanaswamy R. An optical hydroxyl radical sensor. Biosens Bioelectron 1993;8:325-9.
64. Halliwell B, Gutteridge JM. Biologically relevant metal ion dependent hydroxyl radical generation. An update. FEBS Lett 1992;307:108-12.
65. Herbert V, Shaw S, Jayatilleke E, Stopler-Kasdan T. Most free radical injury is iron related: it is promoted by iron, hemin, holoferritin and vitamin C, and inhibited by desferoxamine and apoferritin. Stem Cell Dayt 1994;12:289-303.
66. Burkitt MJ, Mason RP. Direct evidence for in vivo hydroxyl radical generation in experimental iron overload: an ESR spin-trapping investigation. Proc Natl Acad Sci USA 1991;88:8440-4.
67. Lesnefsky EJ, Ye J. Exogenous intracellular but not extracellular iron augments myocardial reperfusion injury. Am J Physiol 1994;266:H384-92.
68. Paller MS, Hedlund BE. Extracellular iron chelators protect kidney cells from hypoxia/reoxygenation. Free Radic Biol Med 1994;17:597-603.
69. Chiao JJ, Kirschner RE, Fantini GA. Iron delocalization occurs during ischemia and persists on reoxygenation of skeletal muscle. J Lab Clin Med 1994;124:432-8.
70. Olakanmi O, McGowan SE, Hayek MB, Britigan BE. Iron sequestration by macrophages decreases the potential for extracellular hydroxyl radical formation. J Clin Invest 1993;91:889-99.
71. Liu M, Okada S. Induction of free radicals and tumours in the kidneys of Wistar rats by ferric ethylenediamine-N,N′-diacetate. Carcinogenesis 1994;15:2817-21.
72. Schapira RM, Ghio AJ, Effros RM, Morrisey J, Dawson CA, Hacker AD. Hydroxyl radicals are formed in the rat lung after asbestos instillation in vivo. Am J Respir Cell Mol Biol 1994;10:573-9.
73. Gerschman R, Gilbert DL, Caccamise D. Effects of various substances on survival times of mice exposed to different higHOxygen tensions. Am J Physiol 1958;192:563-571.
74. Zweier JL, Duke SS, Kuppusamy P, Sylvester JT, Gabrielson EW. Electron paramagnetic resonance evidence that cellular oxygen toxicity is caused by the generation of superoxide and hydroxyl free radicals. FEBS Lett 1989;252:12-16.
75. Kelly FJ, Lubec G. Hyperoxic injury of immature guinea pig lung is mediated via hydroxyl radicals. Pediatr Res 1995;38:286-91.
76. Spatz L, Bloom AD. Biological consequences of oxidative stress. Oxford: Oxford University Press 1992.
77. Halliwell B, Aruoma OI. DNA and free radicals. Prentis Hall: New Jersey, 1993.
78. Jackson JH. Potential molecular mechanisms of oxidant-induced carcinogenesis. Environ Health Perspect 1994;102:155-7.
79. Feng L, Xia Y, Garcia GE, Hwang D, Wilson CB. Involvement of reactive oxygen species in cyclooxygenase-2-expression induced by interleukin 1, tumour necrosis factor-alpha and lipopolysaccharide. J Clin Invest 1995;95:1669-75.
80. Pinkus R, Weiner LM, Daniel V. Role of quinone-mediated generation of hydroxyl radicals in the induction of glutathion S transferase gene expression. Biochemistry 1995;34:81-8.
81. Nottet HS, van Asbeck BS, de Graaf L, de Vos NM, Visser MR, Verhoef J. Role for oxygen radicals in self-sustained HIV-1 replication in monocyte-derived macrophages: enhanced HIV-I replication by N-acetyl-cysteine. J Leukoc Biol 1994;56:702-7.
82. Iuliano L, Pedersen JZ, Pratico D, Rotilio G, Violi F. Role of hydroxyl radicals in the activation of human platelets. Eur J Biochem 1994;221:695-704.
83. Wolcott RG, Franks BS, Hannum DM, Hurst JK. Bactericidal potency of hydroxyl radical in physiological environments. J Biol Chem 1994;269:9721-8.
84. Prinsze C, Dubbelman TM, Van Steveninck J. Protein damage, induced by small amounts of photodynamically generated singlet oxygen or hydroxyl radicals. Biochim Biophys Acta. 1990;1038:152-7.
85. Uchida K, Kato Y, Kawakishi S. A novel mechanism for oxidative cleavage of prolyl peptides induced by the hydroxyl radical. Biochem Biophys Res 1990;169:265-71.
86. Tubaro M, Cavallo G, Pensa V, Chessa MA, Natale E, Ricci R, Milazzotto F, Tubaro E. Demonstration of the formation of hydroxyl radicals in acute myocardial infarction in man using salicylate as probe. Cardiology 1992;80:246-51.
87. Das UN. Can free radicals induce coronary vasospasm and acute myocardial infarction? Med Hypotheses 1992;39:90-94.
88. Maxwell L, Gavin J. Antioxidant therapy improves microvascular ultrastructure and perfusion in postischemic myocardium. Microvasc Res 1992;43:255-66.
89. Pisarenko Ol, Studneva IM, Lakomkin VL, Timoshin M, Kapelko Vl. Human recombinant extracellular superoxide dismutase type C improves cardioplegic protection against ischemia/reperfusion injury in isolated rat heart. J Cardiovasc Pharmacol 1994;24:655-63.
90. Huang HS, Stahl GL, Longhurst JC. Cardiac-cardiovascular reflexes induced by hydrogen peroxide in cats. Am J Physiol 1995;268:H2114-24.
91. Takemura G, Onodera T, Ashraf M. Quantification of hydroxyl radical and its lack of relevance to myocardial injury during early reperfusion after graded ischemia in rat hearts. Circ Res 1992;71:96-105.
92. Hayakawa M, Hattori K, Suglyama S, Ozawa T. Age associated oxygen damage and mutations in mitochondrial DNA in human hearts. Biochem Biophys Res 1992;189:979-85.
93. Ross AD, Varghese G, Oporto B, Carmichael FJ, Israel Y. Effect of propylthiouracil treatment on NADPH-cytochrome P450 reductase levels, oxygen consumption and hydroxyl radical formation in liver microsomes from rats fed ethanol or acetone chronically. Biochem Pharmacol 1995;49:979-89.
94. McCay PB, Reinke LA, Rau JM. Hydroxyl radicals are generated by hepatic microsomes during NADPHOxidation: relationship to ethanol metabolism. Free Radic Res 1992;15:335-46.
95. Baud L, Ardaillou R. Reactive oxygen species: production and role in the kidney. Am J Physiol 1986;251:F765-76.
96. Shah SV. The role of reactive oxygen metabolites in glomerular disease. Ann Rev Physiol 1995;57:245-62.
97. Rehan A, Johnson KJ, Wiggins RC, Kunkel RG, Ward PA. Evidence for the role of oxygen radicals in acute nephrotoxic nephritis. Lab Invest 1994;51:396-403
98. Johnson RJ, Couser WG, Chi KY, Adler S, Klebanoff SJ. New mechanism for glomerular injury. J Clin Invest 1987;79:1379-87.
99. Neale TJ, Ullrich R, Ohja P, Poczewski H, Verhoeven AJ, Kerjaschki D. Reactive oxygen species and neutrophil respiratory burst cytochrome b558 are produced by kidney glomerular cells in passive Heymann nephritis. Proc Natl Acad Sci USA 1993;90:3645-9.
100. Shah SV. Evidence suggesting a role for hydroxyl radical in passive Heymann nephritis in rats. Am J Physiol 1988;254:F337-44.
101. Thakur V, Walker PD, Shah SV. Evidence suggesting a role for hydroxyl radical in puromycin aminonucleoside-induced proteinuria. Kidney Int 1988;34:494-9.
102. Yang CL, Du XH, Han YX. Renal cortical mitochondria are the source of oxygen free radicals enhanced by gentamycin. Ren Fail 1995;17:21-6.
103. Fahn S, Cohen G. The oxidant stress hypothesis in Parkinson's disease: evidence supporting it. Ann Neurol 1992;32:804-12.
104. Chiueh CC, Wu RM, Mohanakumar KP, Sternberger LM, Krishna G, Obata T, Murphy DL. In vivo generation of hydroxyl radicals and MPTP-induced dopaminergic toxicity in the basal ganglia. Ann NY Acad Sci 1994;738:25-36.
105. Maruyama W, Dostert P, Naoi M. Dopamine-derived 1-methyl-6,7dihydroxyisoquinolines as hydroxyl radical promotors and scavengers in the rat brain: in vivo and in vitro studies. J Neurochem 1995;64:2635-43.
106. Wu RM, Mohanakumar KP, Murphy DL, Chiueh CC. Antioxidant mechanism and protection of nigral neurons against MPP+ toxicity by deprenyl (selegiline). Ann NY Acad Sci 1994;738:214-21.
107. Smith TS, Swerdlow RH, Parker WD, Bennett JP. Reduction of MPP(+)-induced hydroxyl radical formation and nigrostriatal MPTP toxicity by inhibiting nitric oxide synthase. Neuroreport 1994;5:2598-600.
108. Schulz JB, Henshaw NW, Siwek D, Jenkins BG, Ferrante RJ, Cipolloni PB, Kowall NW, Rosen BR, Beal MF. Involvement of free radicals in excitotoxicity in vivo. J Neurochem 1995;64:2239-47.
109. Thomas CE, Carney JM, Bernotas RC, Hay DA, Carr AA. In vitro and in vivo activity of a novel series of radical trapping agents in model systems of CNS oxidative damage. Ann NY Acad Sci 1994;738:243-9.
110. Althaus JS, Andrus PK, Williams CM, VonVoigtlander PF, Cazers AR, Hall ED. The use of salicylate hydroxylation to detect hydroxyl radical generation in ischemic and traumatic brain injury. Reversal by tirilazad mesylate(U-74006F). Mol Chem Neuropathol 1993;20:147-62.
111. Zhao W, Richardson JS, Mombourquette MJ, Weil JA. An in vitro EPR study of the free radical scavenging actions of the lazaroid antioxidants U-74500A and U78517F. Free Radic Biol Med 1995;19:21-30.
112. Lubec B, Hayn M, Denk W, Bauer G. Brain lipid peroxidation and hydroxyl radical attack following the intravenous infusion of hydrogren peroxide in an infant. Free Radic Biol Med. In press.
113. Lubec G, Weninger M, Anderson S. Racemization and oxidation studies of hair protein in the Homo tirolensis. FASEB J 1994;8:1166-9.
114. Griffith HR, Lunec J. Effect of polymorph derived oxidants on IgG in relation to rheumatoid factor binding. Scand J Rheumatol 1988;75:148-56.
115. Griffith HR, Lunec J. The effects of oxygen free radicals on the carbohydrate moiety of IgG. FEBS Lett 1989;245:95-9.
116. Greenwald RA. Oxygen radicals, inflammation, and arthritis: pathophysiological considerations and implications for treatment. Semin Arthritis Rheum 1991;20:219-40.
117. Saari H. Oxygen derived free radicals and synovial fluid hyaluronate. Ann Rheum Dis 1991;50:389-92.
118. Saari H, Suomalainen K, Lindy O, Konttinen YT, Sorsa T. Activation of latent human neutrophil collagenase by reactive oxygen species and serine proteases. Biochem Biophys Res Commun 1990;171:979-87.
119. Santos L, Tipping PG. Attenuation of adjuvant arthritis in rats by treatment witHOxygen radical scavengers. Immunol Cell Biol 1994;72:406-14.
120. Hamburger SA, McCay PB. Spin trapping of ibuprofen radicals:evidence that ibuprofen is a hydroxyl radical scavenger. Free Radic Res 1990;9:337-42.
121. Henrotin Y, Deby-Dupont G, Deby C, De-Bruyn M, Lamy M, Franchimont P. Production of active oxygen species by isolated human chondrocytes. Br J Rheumatol 1993;32:562-7.
122. Blount S, Griffith HR, Lunec J. Reactive oxygen species induce antigenic changes in DNA. FEBS Lett 1989;245:100-4.
123. Alam K, Ali A, Ali R. The effect of hydroxyl radical on the antigenicity of native DNA. FEBS Lett 1993;319:66-70.
124. Riesz P, Kondo T. Free radical formation induced by ultrasound and its biological implications. Free Radic Biol Med 1992;13:247-70.
125. Richards WT, Loomis AL. The chemical effects of high frequency sound waves. J Am Chem Soc 1927;49:3086-100.
126. Weissler A, Pecht I, Anbar M. Ultrasound chemical effects on pure organic liquids. Science 1965;150:1288-9.
127. Szalay A. Die Zerstoerung von hochpolymeren Molekulen mittels Ultraschallwellen. Z Phys Chem 1933;A164:234-40.
128. Parke AVM, Taylor D. The chemical action of ultrasonic waves. J Chem Soc 1956;4442-50.
129. Makino K, Mossoba M, Riesz P. Chemical effects of ultrasound in aqueous solutions. Evidence for .OH and .H by spin trapping. J Phys Chem 1982;87:3537-9.
130. Makino K, Mossoba M, Riesz P. Chemical effects of ultrasound on aqueous solutions. Formation of hydroxyl radicals and hydrogen atoms. J Phys Chem 1983;104:1369-77.
131. Flynn H. Generation of transient cavities in liquids by microsecond pulses of ultrasound. J Acoust Soc Am. 1982;72:1926-32.
132. Apfel RE. Acoustic cavitation predicted. J Acoust Soc Am 1981;69:1624-33.
133. Carmichael AJ, Mossoba MM, Riesz P, Christman CL. Free radical production in aqueous solution exposed to simulated ultrasonic diagnostic conditions. IEEE Trans Ultrason Ferroelectric Freq Cont. UFFC 1986;33:148-55.
134. Christman CL, Carmichael AJ, Mossoba M, Riesz P. Evidence for free radicals produced in aqueous solution by diagnostic ultrasound. Ultrasonics 1987;25:31-4.
135. Duck F, Starritt HC, Aindow JD, Perkins MA, Hawkins AJ. The output of pulse-echo ultrasound equipment: a survey of powers, pressures and intensities. Brit J Radiol 1985;58:989-1001.
136. Crum LA, Walton AJ, Mortimer A, Dyson M, Crawford DC, Gaitan DF. Free radical production in amniotic fluid and blood plasma by medical ultrasound. J Ultrasound Med 1987;6:643-7.
137. Kondo T, Fukushima Y, Kon H, Riesz P. Effect of shear stress and free radicals induced by ultrasound on erythrocytes. Arch Biochem Biophys 1989;269:381-9.
138. Kondo T, Gamson J, Mitchell JB, Riesz P. Free radical formation and cell lysis induced by ultrasound in the presence of different rare gases. Int J Radiat Biol 1988;54:955-62.
139. Inoue M, Church CC, Brayman A, Miller MW, Malcuit MS. Confirmation of the protective effect of cysteamine in in vitro ultrasound exposures. Ultrasonics 1989;27:362-9.
140. Fuciarelli AF, Sisk EC, Thomas RM, Miller DL. Induction of base damage in DNA solutions by ultrasonic cavitation. Free Radic Biol Med 1995;18:231-8.
141. Buxton GV, Greenstock CL, Helman WP, Ross AB. Critical review of rate constants for reactions of hydrated electron, H atoms and hydroxyl radical in aqueous solution. J Phys Chem Ref Data 1988;17:513-888.
142. Okutomi T, Nomoto K, Nakamura K, Goto F. Autogenous production of hydroxyl radicals from thiopental. Acta Anaesthesiol Scand 1995;39:338-42.
143. Wiegrebe W, Mueller K. Treatment of psoriasis with enthrones-chemical principles, biochemical aspects and approaches to the design of novel derivatives. Skin Pharmacol 1995;8:1-24.
144. Obata T, Yamanaka Y. Intracranial microdialysis of salicylic acid to detect hydroxyl radical generation by monoamine oxidase inhibitor in the rat. Neurosci Lett 1995;188:13-6.
145. Dahlnaus M, Almstadt E, Henschke P, Luttgert S, Appel KE. Induction of 8-hydroxy-2-deoxyguanosine and single strand breaks in DNA of V79 cells by tetrachloro-p-hydroquinone. Mutat Res 1995;329:29-36.
146. Li Y, Kuppusamy P, Zweier JL, Trush MA. ESR evidence for the generation of reactive oxygen species from the copper mediated oxidation of the benzene metabolite, hydroquinone: role in DNA damage. Chem Biol Interact 1995;94:101-20.
147. Nair UJ, Nair J, Friesen MD, Bartsch H, Oshima H. Ortho- and meta-tyrosine formation from phenylalanine in human saliva as a marker of hydroxyl radical generation during betel quid chewing. Carcinogenesis 1995;16:1195-8.
148. Shen HM, Ong CN, Shi CY. Involvement of reactive oxygen species in aflatoxin B1-induced cell injury in cultured rat hepatocytes. Toxicology 1995;99:115-23.
149. Bradshaw TP, McMillan DC, Crouch RK, Jollow DJ. Identification of free radicals produced in rat erythrocytes exposed to hemolytic concentrations of phenylhydroxylamine. Free Radic Biol Med 1995;18:279-85.
150. Shi X, Dalal NS. Generation of hydroxyl radical by chromate in biologically relevant systems: role for Cr(V) complexes versus tetraperoxochromate(V). Environ Health Perspect 1994;102:231-6.
151. Ueno S, Suglyama M, Susa N. Furukawa Y. Effect of dimethylthiourea on chromium (VI)-induced DNA single strand breaks in Chinese hamster V79 cells. Mutat Res 1995;346:247-53.
152. Schapira RM, Ghio AJ, Effros RM, Morrisey J, Almagro UA, Dawson CA., Hacker AD. Hydroxyl radical production and lung injury in the rat following silica or titanium dioxide instillation in vivo. Am J Respir Cell Mol Biol 1995;12:220-6.
153. Shi X, Mao Y, Ahmed N, Jiang H. HPLC investigation on Ni(II)-mediated DNA damage in the presence of t-butyl-hydroperoxide and glutathione. J Inord Biochem 1995;57:91-102.
154. Kasprzak KS, Zastawny TH, North SL, Riggs CW, Diwan BA, Rice JM, Didzdaroglu M. Oxidative DNA base damage in renal, hepatic and pulmonary chromatin of rats after intraperitoneal injection of cobalt(II) acetate. Chem Res Toxicol 1994;7:329-35.
155. Shi X, Dalal NS. Vanadate mediated hydroxyl radical generation from superoxide radical in the presence of NADH: Haber Weiss vs Fenton mechanisms. Arch Biochem Biophys 1993;307:336-41.
156. Husain S, Hadi SM. Strand scission in DNA induced by L-DOPA in the presence of Cu (II). FEBS Lett 1995;364:75-8.
157. Heo JH, Kim DG. Bahng HR, Kim JS. Dimethylthiourea prevents MPTP-induced decrease in [3H] dopamine uptake in rat striatal slices. Brain Res 1995;671:321-4.
158. Garcia-Martinez P, Winston GW, Metash-Dickey C, O'Hara SC, Livingstone DR. Nitrofurantoin-stimulated reactive oxygen species production and genotoxicity in digestive gland microsomes and cytosol of the common mussel. Toxicol Appl Pharmacol 1995;131:332-41.
159. Shi X, Mao Y, Daniel LN, Saffiotti U, Dalal NS, Vallyathan V. Silica radical-induced DNA damage and lipid peroxidation. Environ Health Perspect 1994;102:149-54.
160. Giovanni A, Liang LP, Hastings TG, Zigmond MJ. Estimating hydroxyl radical content in brain using systemic and intraventricular salicylate: impact of methamphetamine. J Neurochem 1995;64:1819-25.
161. Lee YS, Wurster RD. Methylene blue induces cytotoxicity in human brain tumour cells. Cancer Lett 1995;88:141-5.
162. Ito Y. Photodegradation of the cytosine nucleosides family by water soluble ion (HI) porphyrins. Bioconjug Chem 1993;4:127-33.
163. Paillou N, Fery-Forgues S. Interest of photochemical methods for the induction of lipid peroxidation. Biochimie 1994;76:355-68.
164. Van Zyl JM, Van der Walt BJ. Apparent hydroxyl radical generation without transition metal catalysis and tyrosine nitration during oxidation of the antitubercular drug, isonicotinic acid hydrazide. Biochem Pharmacol 1994;48:2033-42.
165. Du XH, Yang CL. Mechanism of gentamicin nephrotoxicity in rats and the protective effect of zinc-induced metallothionein synthesis. Nephrol Dial Transplant 1994;9:135-40.
166. Paller MS, Jacob HS. Cytochrome P-450 mediates tissue damaging hydroxyl radical formation during reoxygenation of the kidney. Proc Natl Acad Sci USA 1994;91:7002-6.
167. Mon H, Arai T, Mori K, Tsutsui H, Makino K. Use of M4PO and oxygen-17 in the study on hydroxyl radical generation in the hypoxanthine-xanthine oxidase reaction. Biochem Mol Biol Int 1994;32:523-9.
168. Park JW, Floyd RA. Generation of strand breaks and formation of 8-hydroxy2′-deoxyguanosine in DNA by a Thiol/Fe3+/02-catalyzed oxidation system. Arch Biochem Biophys 1994;312:285-91.
169. Ohyagi Y, Yamada T, Goto I. Hemoglobin as a novel protein developmentally regulated in neurons. Brain Res 1994;635:323-7.
170. Van der Walt BJ, Van Zyl JM, Kriegler A. Aromatic hydroxylation during the myeloperoxidase-oxidase oxidation of hydrazines. Biochem Pharmacol 1994;47:1039-46.
171. Hino Y, Kumashiro R, Sata M, Nishi J, Ogura R, Tanikawa K. Hydroxyl radical generation and membrane fluidity of erythrocytes treated with lipopolysaccharide. Free Radic Res 1993;19:S177-84.
172. Muller K, Gurster D. Hydroxyl radical damage to DNA sugar and model membranes induced by anthralin (dianthrol). Biochem Pharmacol 1993;46:1695-704.
173. Ogura R, Suglyama M, Haramaki N, Hidaka T. Electron spin resonance studies on the mechanism of adriamycin-induced heart mitochondrial damages. Cancer Res 1991;51:3555-8.
174. Sam JW, Peisach J. EPR spectroscopic investigation of the lability of oxygen in activated bleomycin-mediated DNA degradation. Biochemistry 1993;32:1488-91.
175. Muniz P, Valls V, Perez-Broseta C, Iradi A, Climent JV, Oiiva MR, Saez GT. The role of 8-hydroxy-2′-deoxyguanosine in rifamycin - induced DNA damage. Free Radic Biol Med 1995;18:747-55.
176. Burkitt MJ, Kadiiska MB, Hanna PM, Jordan SJ, Mason RP. Electron spin resonance spin trapping investigation into the effects of paraquat and desferrioxamine on hydroxyl radical generation during acute iron poisoning. Mol Pharmacol 1993;43:257-63.
177. Pryor WA. Biological effects of cigarette smoke, wood smoke, and the smoke from plastics: the use of electron spin resonance. Free Radic Biol Med 1992;13:659-76.
178. Zhang J, Piantadosi CA. Mitochondrial oxidative stress after carbon monoxide hypoxia in the rat brain. J Clin Invest 1992;90:1193-9.
179. Mikuni T, Tatsuta M, Kamachi M. Hydroxyl radical production by the reaction of N-methyl-N′-nitro-N-nitrosoguanidine with hydrogen peroxide without exposure to light. Biochem Cell Biol 1992;70:262-8.
180. Reiter RJ, Melchiorri D, Sewerynek E, Poeggeler B, Barlow-Walden L, Chuang J, Ortiz GG, Acuna-Castroviejo D. A review of the evidence supporting melatonin's role as an antioxidant. J Pineal Res 1995;18:1-11.
181. Giusti P, Gusella M, Lipartiff M, Milani d, Zhu W, Vicini S, Manev H. Melatonin protects primary cultures of cerebellar granule neurons from kainate but not from N-methyl-aspartate excitotoxicity. Exp Neurol 1995;131:39-46.
182. Miura T, Muraoka S, Ogiso T. Protective effects of beta blockers against 2′2′azobis (2-amidinopropane)-dihydrochloride-induced damage. Chem Biol Interact 1995;97:25-35.
183. Ramos CL, Pou S, Rosen GM. Effect of anti-inflammatory drugs on myeloperoxidase-dependent hydroxyl-radical generation by human neutrophils. Biochem Pharmacol 1995;49:1079-84.
184. Cai Q, Takemura G, Ashraf M. Antioxidative properties of histidine and its effect on myocardial injury during ischemia/reperfusion in isolated rat heart. J Cardiovasc Pharmacol 1995;25:147-55.
185. Naito Y, Yoshikawa T, Tanigawa T, Sakurai K, Yamasaki K, Uchida M, Kondo M. Hydroxyl radical scavenging by rebamipide and related compounds: electron paramagnetic resonance study. Free Radic Biol Med 1995;18:117-23.
186. Matsugo S, Yan W, Han D, Trischler HU, Packer L. Elucidation of antioxidant activity of alpha-lipoic acid toward hydroxyl radical. Biochem Biophys Res Commun 1995;208:161-7.
187. French JF, Thomas CE, Downs TR, Ohlweiler DF, Carr AA, Dage RC. Protective effects of a cyclic nitrone antioxidant in animal models of endotoxin shock and chronic bacteremia. Circ Shock 1994;43:130-6.
188. Reddy AC, Lokesh BR. Studies on the inhibitory effects of cucurmin and eugenol on the formation of reactive oxygen species and the oxidation of ferrous iron. Mol Cell Biochem 1994;137:1-8.
189. Ogawa N, Tanaka K, Asanuma M, Kawai M, Masumizu T, Kohno M, Mori A. Bromocriptine protects mice: against 6-hydroxy-dopamine and scavenges hydroxyl radicals in vitro. Brain Res 1994;657:207-13.
190. Yoshikawa T, Minamiyama Y, Naito Y, Kondo M. Antioxidant properties of bromocriptine, a dopamine agonist. J Neurochem 1994;62:1034-8.
191. Lapenna D, De Gioia S, Mezzetti A, Grossi L, Festi D, Marzio L, Cuccurullo F. Hz-receptor antagonists are scavengers of oxygen radicals. Eur J Clin Invest 1994;24:476-81.
192. Zager RA, Fuerstenberg SM, Baehr PH, Myerson D, Torok-Storb B. An evaluation of antioxidant effects on recovery from postischemic acute renal failure. J Am Soc Nephrol 1994;4:1588-97.
193. Phillis JW, Sen S. Oxypurinol attenuates hydroxyl radical production during ischemia/reperfusion injury of the rat cerebral cortex: an ESR study. Brain Res 1993;628:309-12.
194. Hanasaki Y, Ogawa S, Fukui S. The correlation between active oxygen scavenging and antioxidative effects of flavonoids. Free Radic Biol Med 1994;16:845-50.
195. Nowak D, Antczak A, Krol M, Bialasiewicz P, Pietras T. Antioxidant properties of Ambroxol.Free Radic Biol Med 1994;16:517-22.
196. Oredsson S, Plate G, Qvarfordt P. Experimental evaluation of oxygen free radical scavengers in the prevention of reperfusion injury in skeletal muscle. Eur J Surgery 1994;160:97-103.
197. Yang CL, Du XH, Zhao JH, Chen W, Han YX. Zinc-induced metallothionein synthesis could protect from gentamycin nephrotoxicity in suspended proximal tubules of rats. Renal Fail 1994;16:61-9.
198. Chubatsu LS, Meneghini R. Metallothionein protects DNA from oxidative damage. Biochem J 1993;291:193-8.
199. Carpenter RJ, Angel MF, Morgan RF. Dimethylsulfoxide increases the survival of primariliy ischemic island skin flaps. Otolaryngol Head Neck Surg 1994;110:228-31.
200. Abello PA, Fidler SA, Bulkley GB, Buchman TG. Antioxidants modulate induction of programmed endothelial cell death (apoptosis) by endotoxin. Arch Surg 1994;129:134-40.
201. Misik V, Mak IT, Stafford RE, Weglicki WB. Reactions of captopril with transition metal ions and hydroxyl radicals: an EPR spectroscopy study. Free Radic Biol Med 1993;15:611-9.
202. Franzini E, Sellak H, Hakim J, Pasquier C. Oxidative damage to lysozyme by the hydroxyl radical: comparative effect of scavengers. Biochim Biophys Acta 1993;1203:11-7.
203. Pasquier C, Franzini E, Abedinzadeh Z, Kaouadji MN, Hakim J. Gamma and pulse radiolysis study of pentoxifylline, a methylxanthine. Int J Radiat Biol 1991;60:433-47.
204. Shi X, Dalal NS, Jain AC. Antioxidant behaviour of caffeine: efficient scavenging of hydroxyl radicals. Food Chem Toxicol 1991;29:1-6.
205. Hicks M, Wong LS, Day RO. Identification of products from oxidation of uric acid induced by hydroxyl radicals. Free Radic Res 1993;18:337-51.
206. Kvam C, Granese D, Flalbani A, Pollesello P, Paoletti S. Hyaluronan can be protected from free radical depolymerization by 2,6-diisopropylphenol, a novel radical scavenger. Biochem Biophys Res Commun 1993;193:927-33.
207. Das KC, Misra HP. Lidocaine: a hydroxyl radical scavenger and singlet oxygen quencher. Mol Cell Biochem 1992;115:179-85.
208. Haseloff RF, Blasig IE, Meffert H, Ebert B. Hydroxyl radical scavenging and antipsoriatic activity of benzoic acid derivatives. Free Radic Biol Med 1990;9:111-5.
209. Aruoma OI, Evans PJ, Kaur H, Sutcliffe L, Halliwell B. An evaluation of the antioxidant and potential pro-oxidant properties of food additives and of trolox C, vitamin E and probucol. Free Radic Res 1990;10:143-57.
210. Himori N, Suzuki T, Ueno K. Aniracetam, a pyrrolidone type cognition enhancer, attenuates the hydroxyl free radical formation in the brain of mice with brain ischemia. J Pharm Pharmacol 1995;47:253-8.
211. Fischer-Nielsen A, Jeding IB, Loft S. Radiation-induced formation of 8-hydroxy-2′-deoxyguanosine and its prevention by scavengers. Carcinogenesis 1994;15:1609-12.