Xenobiotic toxicity mediated by oxigen free radicals;Toxicidad de xenobioticos mediada por radicales libres de oxigeno

Ars Pharmaceutica

Volumn 39, Issue 1, 1998, Pages 5-18

  Martinez Cayuela M ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Oxygen free radicals; Redox cycling; Xenobiotic toxicity

Indexed keywords

OXYGEN RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUPEROXIDE; XENOBIOTIC AGENT;

ARTICLE; CELL DAMAGE; OXIDATION REDUCTION REACTION; TOXICITY; XENOBIOTIC METABOLISM;

EID: 0032452921     PISSN: 00042927     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (99)

1. AIKENS J. and DIX T. A. (1991). Perhydroxyl radical (HOO) initiated lipid peroxidation: the role of fatty acid hydroperoxides. J. Biol. Chem., 266: 15091-15098.
2. 4 in rat liver microsomal fractions, isolated hepatocytes and in vivo in the rat. Biochem. J., 204: 593-603.
3. AMSTRONG R. S., SOHAL R. G., CUTLER R. G. and SLATER T. F. (eds) (1984). Free Radicals Molecular Biology, Aging and Disease. Raven, New York.
4. BAUTISTA A. P. and SPITZER J. J. (1992). Acute ethanol intoxication stimulates superoxide anion production by in situ perfused rat liver. Hepatology, 15: 892-898.
5. BIRNBOIM H. C. and KANABUS-KAMINSKA M. (1985). The production of DNA strand breaks in human leukocytes by superoxide may involve a metabolic process. Proc. Natl. Acad. Sci. USA, 82: 6820-6824.
6. BLAKE D. R., RALLEN R. E. and LUNEC J. (1987). Free radicals in biological systems-a review orientated to inflammatory processes. Br. Med. Bull., 45: 371-385.
7. BUETTNER G. R. and OBERLEY L. W. (1979). The production of hydroxyl radical by tallysomycin and copper (II). FEBS Lett., 101: 333-335.
8. CADENAS E. (1989). Biochemistry of oxygen toxicity. Annu. Rev. Biochem., 51: 79-110.
9. CARP H., MILLER P., HOIDAL J. R. and JANOFF A. (1982) Potential mechanism for emphysema alfa-1-proteinase inhibitor recovered from lungs of cigarette smokers contains oxidized methionine and has decreased elastase inhibitory capacity. Proc. Natl. Acad. Sci. USA, 79: 2041-2045.
10. CAVANAGH J. B. (1984). The problems of neurons with long axons. Lancet, 1: 1284-1287.
11. CERUTTI P. A. (1985). Prooxidant states and tumor promotion. Science, 227: 375-381.
12. CHIGNELL C. F., MOTTEN A. G. and BUETTNER G. R. (1985). Photoinduced free radicals from chlorpromazine and related phenothiazines: relationship to phenothiazine-induced photosensitization. Envir. Htlth. Pers., 64: 103-108.
13. CHOE M., JACKSON C. and YU B. P. (1995). Lipid peroxidation contributes to age-related membrane rigidity. Free Radical Biol. Med., 18: 977-984.
14. CHOI J. H. and YU B. P. (1995), Brain synaptosomal aging free radicals and membrane fluidity. Free Radical Biol. Med., 18(2): 133-139.
15. COTGREAVE I. A., MOLDEUS P. and ORRENIUS (1988). Host defense mechanism against prooxidants. Annu. Rev. Pharmacol. Toxicol., 28: 189-212.
16. DAVIES K. J. A., WIESE A. G., SEVANIAN A. and KIM E. H. (1990). Repair systems in oxidative stress. In: Finch C. E., Johnson T. E. (eds). Molecular Biology of Aging, Wiley-Liss, New York.
17. DE VRIES J. (1981). Hepatotoxic metabolic activation of paracetamol and its derivatives phenacetine and benorilate: oxygenation or electron transfer?. Biochem. Pharmacol., 30: 399-402.
18. DEMPLE B. and LINN S. (1982). 5,6-saturated thymine lesions in DNA: production by ultraviolet light or hydrogen peroxide. Nucleic Acids Res., 10: 3781-3789.
19. DEMPLE B. (1990). Oxidative DNA damage: repair and inducible cellular responses. Mutat. Environ.,A, 155-167.
20. DUTHIE G. G., WAHLE K. J. (1990). Smoking, antioxidants essential fatty acids and coronary heart disease. Biochem. Transac., 18: 1051-1054.
21. FARRINGTON J. A., EBERT M., LAND E. J. and FLETCHER K. (1973). Bipyridylium quaternary salts and related compounds. Pulse radiolysis studies of the reaction of paraquat radical wit oxyge. Implications for the mode of action od bipyridyl herbicides. Biochim. Biophys. Acta, 314: 372-380.
22. FISCHER V., WEST P. R., NELSON S. D. HARVISON P. J. and MASON R. P. (1985). Formation of 4-aminophenoxyl free radical from the acetaminophen metabolite N acetyl p-benzoquinone imine. J. Biol. Chem., 260: 11446-11450.
23. FORNI L. G., PACKER J. E., SLATER T. F. and WILLSON R. L. (1983). Reaction of the trichloromethyl and halothane-derived peroxy radicals with unsaturated fatty acids: a pulse radiolysis study. Chem. Biol. Interact., 45: 171-177.
24. FRANK L. (1981). Prolonged survival after paraquat. Role of the lung antioxidant enzyme systems. Biochem. Pharmacol., 30: 2319-2324.
25. FREEMAN B. A. and GRAPO J. D. (1982). Biology of disease. Free radicals and tissue injury. Lab. Invest., 47: 412-426.
26. FRIDOVICH I. (1983). Superoxide radical: an endogenous toxicant. Annu. Rev. Pharmacol. Toxicol., 23: 239-257.
27. GEBICKI S. and GEBICKI J. M. (1993). Formation of peroxides in amino acids and proteins exposed to oxygen free radicals. Biochem. J., 289: 743-749.
28. GREEN G. M. (1985). Mechanisms of tobacco smoke toxicity on pulmonary macrophage cells. Eur. J. Respir. Dis., 66: 82-85.
29. GREENWALD R. W. and MOY W. W. (1980). Effect of oxygen- derived free radicals on hyaluronic acid. Arthritis Rheum., 23: 455-463.
30. GUTTERIDGE J. M. C. and HALLIWELL B. (1990). The measurement and mechanism of lipid peroxidation in biological systems. Trends Biochem. Sci., 15: 129-135.
31. HALLIWELL B. and GUTTERIDGE J. M. C. (1984). Oxygen toxicity, oxygen radicals, transition metals and disease. Biochem. J., 219: 1-14.
32. HALLIWELL B. and GUTTERIDGE J. M. C. (eds) (1989). Free Radicals in Biology and Medicine, 2nd edn., Oxford University Press, Clarendon, Oxford.
33. HALLIWELL B. and GUTTERIDGE J. M. C. (1992). Biologically relevant metal ion-dependent hydroxyl radical generation. FEBS Lett., 307: 108-112.
34. HALLIWELL B., GUTTERIDGE J. M. C. and CROSS C. E. (1992). Free radicals, antioxidants, and human disease. Where are we now. J. Lab. Clin. Med., 119: 598-620.
35. HARMAN D. (1992). Role of free radicals in aging and disease. Ann. N. Y. Acad Sci. USA, 673: 126-141.
36. HECHT S. M. (1986). DNA Strand scission by activated bleomycin group antibiotics. Fed. Proc., 45: 2784-2791.
37. HEIKKILA R. E., COHEN G. and MANIAN A. A. (1975). Reactivity of various phenothiazine derivatives with oxygen and oxygen radicals. Biochem. Pharmacol., 24: 363-368.
38. HIGUCHI Y. and LINN S. (1995). Purification of all forms of HeLa cell mitochondrial DNA and assessment of damage to it caused by hydrogen peroxide treatment of mitochoondrial or cells. J. Biol. Chem., 270: 7950-7956.
39. HILL H. A. O. and THORNALLEY P. J. (1983). The effect of spin-traps on phenylhydrazine-induced haemolysis. Biochim. Biophys. Acta, 762: 42-49.
40. HODGSON E. K. and FRIDOVICH I. (1975). The interaction of bovine erythrocyte superoxide dismutase with hydrogen peroxide: inactivation of the enzyme. Biochemistry, 14: 5294-5303.
41. 2 and the yield of DNA strand break in cells of different species. Biochim. Biophys. Acra, 781: 234-238.
42. HORTON A. A. and FAIRHURST S. (1987). Lipid peroxidation and mechanism of toxicity. CRC Crit. Rev. Toxicol., 18: 27-79.
43. HUBER S. A. (1992). Heat-shock induction in adriamycin and picornavirus-infected cardiocytes. Lab. Invest. 67: 218-224.
44. HUNNINGHAKE G., GADEK J. and CRYSTAL R. (1980). Mecahanism by which cigarette smoke attracts polymorphonuclear leukocytes to lung. Chest, 77: 273.
45. IMLAY J. A. and LINN S. (1988). DNA damage and oxygen radical toxicity. Science, 240: 1302-1309.
46. JACOB R. A. (1995). The integrated antioxidam system. Nutr. Rev., 15: 755-766.
47. JAMIESON D. (1989) Oxygen toxicity and reactive oxygen metabolites in mammals. Free Rad. Biol. Med., 7: 87-108.
48. KAPPUS H. and SIES H. (1981). Toxic drug effects associated with oxygen metabolism: redox cycling and lipid peroxidation. Experentia, 37: 1233-1237.
49. KAPPUS H. (1986). Overview of enzyme systems involved in bioreduction of drugs and in redox cycling. Biochem. Pharmac., 35: 1-7.
50. KING T. E., MASON H. S. and MORRISON M. (eds) (1982). Oxidases and Related Redox Systems. Pergamon Press, Oxford.
51. KONO Y. and FRIDOVICH I. (1982). Superoxide radical inhibits catalase. J. Biol Chem., 257: 5751-5761.
52. KORNBRUST D. J. and MAVIS R. D. (1980). Microsomal lipid peroxidation. Stimulation by carbon tetrachloride. Mol. Pharmac., 17: 408-413.
53. LEVEY G., RIEGER A. L. and EDWARDS J. O. (1981). Rates and mechanisms for oxidation of paraquat and diquat radical carions by several peroxides. J. Org. Chem., 46: 1255-1259.
54. LÖVSTAD R. A. (1975). Kinetic studies of the ceruloplasmin-catalyzed oxidation of phenothiazine derivatives. Biochem. Pharmacol., 24: 475-478.
55. MALMSTRÖM B. G. (1982). Enzymology of oxygen. Annu. Rev. Biochem., 51: 21-59.
56. MARTIN W. J. (1983). Nitrofurantoin evidence for the oxidant injury of lung parenchymal cells. Am. Rev. Resp. Dis . 127: 482-486.
57. MARTLNEZ-CAYUELA, M. (1995). Oxygen free radicals and human disease. Biochimie, 77: 147-161.
58. MASON R. P. (1982). Free-radical intermediates in the metabolism of toxic chemicals. In: Pryor W. A. (ed) Free Radicals in Biology, 5. Academic Press, New York, pp. 161-173.
59. MELLO-PILHO A. C., HOFFMANN M. E. and MENEGHINI R. (1984) Cell killing and DNA damage by hydrogen peroxide are mediated by intracellular iron. Biochem. J., 218: 273-275.
60. MYERS C. E., MCGUIRE W. P., LISS R. H., IPRIM I., GROTZINGER K. and YOUNG R. C. (1977). Adriamycin: the role of lipid peroxidation in cardiac toxicity and tumour response. Science, 197: 165-167.
61. NASTAINCZYK W., AHR H. and ULRICH V. (1981). The mechanism of the reductive dehalogenation of polyhalogenated compounds by microsomal cytochrome P450. Adv. Exp. Med. Biol., 136: 799-808.
62. NIELSEN H. (1981). Covalent binding of peroxidized phospholipid to protein. III. Reaction of individual phospholipids with different proteins. Lipids, 16: 215-222.
63. NIKI E., YAMAMOTO Y., KOMURO E. and SATO E. (1991). Membrane damage due to lipid oxidation. Am. J. Clin. Nutr., 53: 2015-2055.
64. PARIZADA B., ERBER M. M. and NIROD A. (1991). Protective effects of human recombinant MnSOD in adjuvant arthritis and bleomycin-induced lung fibrosis. Free Rad. Res. Commun., 15: 297-301.
65. PETERSON F. J., COMBS G. F., HOLTZMAN J. L. and MASON R. (1982). Metabolic activation of oxygen by nitrofurantoin in the young chick. Toxicol. Appl. Pharmacol., 65: 162-169.
66. PROCTOR P. H. and REYNOLDS E. S. (1984). Free radicals and disease in man. Physiol. Chem. Phys., 16: 175-195.
67. PRYOR W. A. (1986) Oxy-radicals and related species: their formation, life-times, and reactions. Annu. Rev. Physiol., 48: 657-667.
68. PRYOR W. A. and CHURCH D. P. (1991). Aldehides, hydrogen peroxide, and organic radical as mediators of oxygen toxicity. Free Rad. Biol Chem., 11: 41-46.
69. PRYOR W. A. and DOOLEY M. M. (1985). Inactivation of alpha-1 proteinase inhibitor by cigarette smoke: effect of smoke phase and buffer. Am. Rev. Respir. Dis., 131: 941-943.
70. 32P-postlabeling. Mutat. Res. 275: 355-366.
71. RICEEVANS C. and BURDON R. (1993). Free radical lipid interactions and their pathological consequences. Prog. Lipid Res., 37: 37-110.
72. RICHMOND R. and HALLIWELL B. (1982). The formation of hydroxyl radicals from the paraquat radical cation, demonstrated by a highly-specific gas Chromatographic technique. The role of superoxide radical anion, hydrogen peroxide and glutathione reductase. J. Inorg. Biochem., 17: 95-101.
73. ROTH W. J., CHUNG S. I. and JANOFF A. (1986). Inactivation of alveolar macrophage transglutaminase by oxidants in cigarette smoke. J. Leuk. Biol., 39: 629-644.
74. SALIM A. S. (1992). Use of scavening oxygen-derived free radicals to protect the rat against aspirin- and ethanol-induced erosive gastritis. J. Pharm. Sci., 81: 943-946.
75. SCHAICH K. H. (1992). Metals and lipid oxidation. Cotemporary issues. Lipids, 27: 209-218.
76. SEVANIAN A., STEIN R. A. and MEAD J. F. (1981). Metabolism of epoxidized phospatidylcholine by phospholipase A2 and epoxide hydrolase. Lipids, 16: 781-788.
77. 2-fumigated leaves of spinach. Plant Cell Physiol., 21: 1193-1200.
78. SIES H. (ed) (1985). Oxidative Stress. Academic Press, London.
79. SINHA B. K. (1983). Enzymatic activation of hydrazine derivatives. A spin-trapping study. J. Biol. Chem., 258: 796-801.
80. SINHA B. K. and MIMNAUGH E. G. (1990). Free radicals and anticancer drug resistance: oxygen free radicals in the mechanism of drug cytotoxicity and resistance by certain tumours. Free Rad. Biol. Med., 8: 567-581.
81. SMITH L. L. (1986). The response of the lung to foreign compounds that produce free radicals. Ann. Rev. Physiol., 48: 681-692.
82. SOUTHORN P. A. and POWIS G. (1988). Free radicals in medicine. I. Chemical nature and biologic reactions. Mayo Clin. Proc., 63: 381-389.
83. STADTMAN E. R. (1992). Protein oxidation and aging. Science, 257: 1220-1224.
84. SUMMERFIELD M. and TUDHOPE G. R. (1978). Studies with primaquine in vitro. Superoxide radical formation and oxidation of haemoglobin. Br. J. Clin. Pharm., 6: 319-323.
85. TABUENCA J. M. (1981). Toxic-allergic syndrome caused by injection of rapessed oil denatured with aniline. Lancet, ii: 567-568.
86. TOMASI A., BILLING S., GARNER A., SLATER T. F. and ALBANO E. (1983). The metabolism of halothane by hepatocytes: a comparison between free radical spin trapping and lipid peroxidation in relation to cell damage. Che.-Biol. Interact., 46: 353-369.
87. THORNALLEY P. J., STERN A. and BANNISTER J. V. (1983). A mechanism for primaquine mediated oxidation of NADPH in red blood cells. Biochem. Pharmacol., 32: 3571-3575.
88. TOTH K. M., BERGER E. M., BEEHLER C. J. and REPINE J. E. (1986). Erytfrocytes from cigarette smokers contain more glutathione and catalase and protect endotelial cells from hydrogen peroxide better than do erythrocytes from nonsmokers. Am. Rev. Respir. Dis., 134: 281-284.
89. TRUSH M. A., MIMNAUGH E. G. and GRAM T. E. (1982). Activation of pharmacologic agents to radical intermediates. Implications for the roles of free radicals in drug action and toxicity. Biochem. Pharmac , 31: 3335-3343.
90. UNVERFERTH D. V., MAGORIEN R., LEIR C. V. y BALCERZAK S. (1982). Doxorrubicin cardiotoxicity. Cancer Treat. Rev., 9: 149-164.
91. VALENZUELA A. (1991). The biological significance of malondialdehide determination in the assessment of tissue oxidative stress. Life Sci., 48: 301-309.
92. VIDELA L. A. and VALENZUELA A. (1982). Alcohol ingestion, liver glutathione and lipoperoxidation: metabolic inter-relations and pathological implications. Life Sci., 31: 2395-2403.
93. WEBSTER N. R. and NUNN J. P. (1988). Molecular structure of free radicals and their importance in biological reactions. Br. J. Anaesth., 60: 98-108.
94. WILLSON R. L. (1977). Metronidazole (Flagil*) in cancer radiotherapy: a historical introduction. In Metronidazole: Proceedings, Montreal May 26-28th 1976. Exerpta Medica.
95. WOLFF S. P. and DEAN R. T. (1986). Fragmentation of protein by free radicals and its effect on their suceptibility to enzymic hydrolysis. Biochem. J., 2234: 399-403.
96. WOLPP S. P., GARNER A. and DEAN R. T. (1986). Free radicals lipids and protein degradation. Trends Biochem. Sci., 11: 27-31.
97. YOUNGMAN R. J., OSSWALD W. F. and ELSTNER E. F. (1982). Cripto-OH radical production by nitrofurantoin. Biochem. Pharmacol., 31: 603-609.
98. YOYNGMAN R. J., OSSWALD W. F. and ELSTNER E. F. (1982). Mechanism of oxygen activation by nitrofurantoin and relevance to its toxicity. Biochem. Pharmacol., 31: 3723-3729.
99. YU B. P. (1994). Cellular defenses against damage from reactive oxygen species. Physiol. Rev., 74: 139-163.