Oxidized proteins and their contribution to redox homeostasis

Redox Report

Volumn 10, Issue 4, 2005, Pages 175-185

  Martínez Sánchez, Gregorio ^a   Giuliani, Attilia ^b   Pérez Davison, Gema ^a   León Fernández, Olga Sonia ^a  

^a UNIVERSITY OF HAVANA   (Cuba)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

Oxidized proteins; Redox homeostasis

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID; BIOLOGICAL MARKER; GLUTATHIONE; PENICILLAMINE; PROTEIN; PROTEINASE; RADICAL; REACTIVE OXYGEN METABOLITE; TOCOPHEROL; TROLOX C;

ANTIOXIDANT ACTIVITY; ARTERIOSCLEROSIS; BIOACCUMULATION; CELL AGING; CELL DAMAGE; CELL GROWTH; DEGENERATIVE DISEASE; DIABETES MELLITUS; ENZYME DEGRADATION; EXTRACELLULAR SPACE; HUMAN; IN VIVO STUDY; INTRACELLULAR SPACE; MAMMAL; NONHUMAN; OXIDATION; OXIDATION REDUCTION STATE; PRIORITY JOURNAL; PROTEIN DEFECT; PROTEIN DEGRADATION; PROTEIN FOLDING; PROTEIN FUNCTION; PROTEIN SYNTHESIS; PROTEIN TARGETING; REGULATORY MECHANISM; REVIEW; SCAVENGING SYSTEM; SUPPLEMENTATION;

ANIMALS; ANTIOXIDANTS; FREE RADICALS; HOMEOSTASIS; HUMANS; MODELS, BIOLOGICAL; NEURODEGENERATIVE DISEASES; OXIDATIVE STRESS; OXYGEN; PROTEINS; REACTIVE OXYGEN SPECIES;

MAMMALIA;

EID: 33746328384     PISSN: 13510002     EISSN: 13510002     Source Type: Journal    
DOI: 10.1179/135100005X57382     Document Type: Review

References (90)

1. Adams GE, Willson RL, Aldrich JE, Cundall RB. On the mechanism of radiation induced inactivation of lysozyme in dilute aqueous solutions. Int J Radiat Biol 1969; 16: 333-342.
2. Carp H, Janoff A. In vitro suppression of serum elastase-inhibitory capacity by reactive oxygen species generated by phagocytosing polymorphonuclear leukocytes. J Clin Invest 1979; 63:793-797.
3. Steinberg D, Parthasarathy S, Carew TE, Khoo JC, Witztum JL. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N Engl J Med 1989; 320: 915-924.
4. Stadtman ER, Levine RL. Protein oxidation. Ann AY Acad Sci 2000; 899: 191-208.
5. Davies MJ. The oxidative environment and protein damage. Biochim Biophys Acta 2005; 1703: 93-109.
6. Hawkins CL, Davies MJ. Generation and propagation of radical reactions on proteins. Biochim Biophys Acta 2001; 1504: 196-219.
7. Stadtman ER, Levine RL. Free radical-mediated oxidation of free amino acids and amino acid residues in proteins. Amino Acids 2003; 25: 207-218.
8. Alvarez B, Radi R. Peroxynitrite reactivity with amino acids and proteins. Amino Acids 2003; 25: 295-311.
9. Dean RT, Fu S, Stocker R, Davies MJ. Biochemistry and pathology of radical-mediated protein oxidation. Biochem J 1997; 324: 1-18.
10. Grune T, Reinheckel T, Davies KJA. Degradation of oxidized proteins in K562 human hematopoietic cells by proteasome. J Biol Chem 1996; 271: 15504-15509.
11. Davies KJA, Goldberg AL. Oxygen radicals stimulate intracellular proteolysis and lipid peroxidation by independent mechanisms in erythrocytes. J Biol Chem 1987; 262: 8220-8226.
12. Grune T, Reinheckel T, Davies KJA. Degradation of oxidized proteins in mammalian cells. FASEB J 1997; 11: 526-534.
13. Stadtman ER. Protein oxidation and aging. Science 1992; 257: 1220-1224.
14. Berlett BS, Levine RL, Stadtman ER. Comparison of the effects of ozone on the modification of amino acid residues in glutamine synthetase and bovine serum albumin. J Biol Chem 1996; 271: 4177-4182.
15. Dukan S, Farewell A, Ballesteros M, Taddei F, Radman M, Nystro MT. Protein oxidation in response to increased transcriptional errors. Proc Natl Acad Sci USA 2000; 97: 5746-5749.
16. Droge W. Free radicals in the physiological control of cell function. Physiol Rev 2002; 82: 47-95.
17. Grune T, Merker K, Sandig G, Davies KJA. Selective degradation of oxidatively modified protein substrates by the proteasome. Biochem Biophys Res Commun 2003; 305: 709-718.
18. Davies MJ, Fu S, Wang H, Dean RT. Stable markers of oxidant damage to proteins and their application in the study of human disease. Free Radic Biol Med 1999; 27: 1151-1163.
19. Griffiths HR. Antioxidants and protein oxidation. Free Radic Res 2000; 33: S47-S58.
20. Witko-Sarsat V, Friedlander M, Khoa TN et al. Advanced oxidation protein products as novel mediators of inflammation and monocyte activation in chronic renal failure. J Immunol 1998; 161: 2524-2532.
21. Griffiths HR, Moller L, Bartosz G et al. Biomarkers. Mol Aspect Med 2002; 23: 101-208.
22. Popov I, Lewin G. Photochemiluminescent detection of antiradical activity. VI. Antioxidant characteristics of human blood plasma, low density lipoprotein, serum albumin and aminoacids during in vitro oxidation. Luminescence 1999; 14: 169-174.
23. Berlett BS, Stadtman ER. Protein oxidation in aging, disease, and oxidative stress. J Biol Chem 1997; 272: 20313-20316.
24. Stadtman ER, Berlett BS. Fenton chemistry. Amino acid oxidation. J Biol Chem 1991; 266: 17201-17211.
25. Headlam HA, Davies MJ. Markers of protein oxidation: different oxidants give rise to variable yields of bound and released carbonyl products. Free Radic Biol Med 2004; 36: 1175-1184.
26. Griffiths HR, Bevan R, Lunec J. Measurement of oxidised amino acids by HPLC. In: Lunec J, Griffiths HR. (eds) Handbook of Oxidative Methods. London: Wiley, 2000: 27-50.
27. Schacter E, Williams JA, Stadtman ER, Levine RL. Determination of carbonyl groups in oxidised proteins. In: Punchard A, Kelly FJ. (eds) Free Radicals. A Practical Approach. Oxford: IRL Press, 1996; 159-170.
28. Buss H, Chan TP, Sluis KB, Domigan NM, Winterbourn CC. Protein carbonyl measurement by a sensitive ELISA method. Free Radic Biol Med 1997; 23: 361-366.
29. Carty JL, Bevan R, Waller H et al. The effects of vitamin C supplementation on protein oxidation in healthy volunteers. Biochem Biophys Res Commun 2000; 273: 729-735.
30. Creed D. The photochemistry and photophysics of the near UV absorbing amino acids. III Cystine and its simple derivatives. Photochem Photobiol 1984; 39: 577-584.
31. Petropoulos I, Mary J, Perichon M, Friguet B. Rat peptide methionine sulphoxide reductase: cloning of the cDNA, and down-regulation of gene expression and enzyme activity during aging. Biochem J 2001; 355: 819-825.
32. Biewenga GP, Veening-Griffioenen DH, Nicastia AJ, Haenen GRMM. Effects of dihydrolipoic acid on peptide methionine sulfoxide reductase implications for antioxidant drugs. Arzneimittelforschung 1998; 48: 144-148.
33. Ellman GL. Tissue sulphydryl groups. Arch Biochem Biophys 1959; 82: 70-77.
34. Singh R, Blattler WA, Collinson AR. An amplified assay for thiols based on reactivation of papain. Anal Biochem 1993; 213: 49-56.
35. Fu S, Gebicki S, Jessup W, Gebicki JM, Dean RT. Biological fate of amino acid, peptide and protein hydroperoxides. Biochem J 1995; 311: 821-827.
36. Robinson S, Bevan R, Lunec J, Griffiths H. Chemiluminescence determination of hydroperoxides following radiolysis and photolysis of free amino acids. FEBS Lett 1998; 430: 297-300.
37. Morgan PE, Dean RT, Davies MJ. Protective mechanisms against peptide and protein peroxides generated by singlet oxygen. Free Radic Biol Med 2004; 36: 484-496.
38. Fu SL, Dean RT. Structural characterization of the products of hydroxyl-radical damage to leucine and their detection on proteins. Biochem J 1997; 324: 41-48.
39. Morin B, Bubb WA, Davies MJ, Dean RT, Fu S. 3-Hydroxylysine, a potential marker for studying radical-induced protein oxidation. Chem Res Toxicol 1998; 11: 1265-1273.
40. Requena JR, Stadtman ER. Conversion of lysine to N(epsilon)-(carboxymethyl)lysine increases susceptibility of proteins to metal-catalyzed oxidation. Biochem Biophys Res Commun 1999; 264: 207-211.
41. Young JF, Nielsen SE, Haraldsdottir J et al. Effect of fruit juice intake on urinary quercetin excretion and biomarkers of antioxidative status. Am J Clin Nutr 1999; 69: 87-94.
42. 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.
43. Kato Y, Miyake Y, Yamamoto K et al. Preparation of a monoclonal antibody to N(epsilon)-(hexanonyl)lysine: application to the evaluation of protective effects of flavonoid supplementation against exercise-induced oxidative stress in rat skeletal muscle. Biochem Biophys Res Commun 2000; 274: 389-393.
44. Guptasarma P, Balasubramania D, Matsugo S, Saito I. Hydroxyl radical mediated damage to proteins, with special reference to the crystallins. Biochemistry 1992; 31: 4296-4303.
45. Maskos Z, Rush JD, Koppenol WH. The hydroxylation of tryptophan. Arch Biochem Biophys 1992; 262: 521-529.
46. Hawkins CL, Davies MJ. Hypochlorite-induced oxidation of proteins in plasma: formation of chloramines and nitrogen-centred radicals and their role in protein fragmentation. Biochem J 1999; 340: 539-548.
47. Griffiths HR, Lunec J, Blake DR. Oxygen radical induced fluorescein proteins; identification of the fluorescent tryptophan kynurenine, as a biological index of radical damage. Amino Acids 1992; 3: 183-194.
48. Giessauf A, van Wickern B, Simat T, Steinhart H, Esterbauer H. Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation. FEBS Lett 1996; 389: 136-140.
49. 2. J Biol Chem 1992; 267: 8827-8833.
50. Rodgers KJ, Hume PM, Dunlop RA, Dean RT. Biosynthesis and turnover of DOPA-containing proteins by human cells. Free Radic Biol Med 2004; 37: 1756-1764.
51. Witko-Sarsat V, Nguyen-Khoa T, Jungers P, Drueke TB, Descamps-Latscha B. Advanced oxidation protein products as a novel molecular basis of oxidative stress in uraemia. Nephrol Dial Transplant 1999; 14: 76-78.
52. Yuan F, Liu SX, Tian JW. Advanced oxidation protein products induced reactive oxygen species production in endothelial cells. Di Yi Jun Da Xue Xue Bao 2004; 24: 1350-1352.
53. Witko-Sarsat V, Gausson V, Descamps-Latscha B. Are advanced oxidation protein products potential uremic toxins?. Kidney Int Suppl 2003; 84: S11-S14.
54. Yazici C, Kose K, Calis M, Delmlr M, Kimap M, Ates F. Increased advanced oxidation protein products in Bechoet's disease: a new activity marker? Br J Dermatol 2004; 151: 105-111.
55. Martínes-Sánchez G, Al-Dalain SM, Popov I, Menendez S, Guiliani A, León OS. Contribution to characterization of oxidative stress in diabetes patients with macroangiopathic complications. Acta Farm Bonaerese 2005; 24: 197-203.
56. Kato Y, Maruyama W, Naoi M, Hashizume Y, Osawa T. Immunohistochemical detection of dityrosine in lipofuscin pigments in the aged human brain. FEBS Lett 1998; 439: 231-234.
57. Winterbourn CC, Kettle AJ. Biomarkers of myeloperoxidase-derived hypochlorous acid. Free Radic Biol Med 2000; 29: 403-409.
58. Hazen SL, d'Avignon A, Anderson MM, Hsu FF, Heinecke JW. Human neutrophils employ the myeloperoxidase-hydrogen peroxide-chloride system to oxidize alpha-amino acids to a family of reactive aldehydes. Mechanistic studies identifying labile intermediates along the reaction pathway. J Biol Chem 1998; 273: 4997-5005.
59. Crow JP. Measurement and significance of free and protein-bound 3-nitrotyrosine, 3-chlorotyrosine, and free 3-nitro-4-hydroxy-phenylacetic acid in biologic samples: a high-performance liquid chromatography method using electrochemical detection. Methods Enzymol 1999; 301: 151-160.
60. Reddy S, Halliwell B, Jones AD, Longhurst JC. The use of phenylalanine to detect hydroxyl radical production in vivo: a cautionary note. Free Radic Biol Med 1999; 27: 1465.
61. Shigenaga MK. Quantitation of protein-bound 3-nitrotyrosine by high-performance liquid chromatography with electrochemical detection. Methods Enzymol 1999; 301: 27-40.
62. Whiteman M, Halliwell B. Loss of 3-nitrotyrosine on exposure to hypochlorous acid: implications for the use of 3-nitrotyrosine as a bio-marker in vivo. Biochem Biophys Res Commun 1999; 258: 169-172.
63. Pacifici RE, Devis KJA. Protein degradation as an index of oxidative stress. Methods Enzymol 1990; 186 B: 485-502.
64. Popov I, Volker H, Lewin G. Photochemiluminescent detection of antiradical activity. V. application in combination with the hydrogen peroxide-initiated chemiluminescence of blood plasma proteins to evaluate antioxidant homeostasis in human. Redox Report 2000; 6: 42-48.
65. Lewin G, Kuhn G, Deuse U, Buhring M, Ramsauer B, Popov I. Paradox of the antiradical capacity of blood plasma protein. In. SFRR Europe Summer Meeting, July 2-5, 1999, Dresden, Germany, Abstract Book, p 029.
66. Bedossa P, Houglum K, Trautwein C, Holstege A, Chojkier M. Stimulation of collagen alpha 1(I) gene expression is associated with lipid peroxidation in hepatocellular injury: a link to tissue fibrosis? Hepatology 1994; 19: 1262-1271.
67. Paradis V, Mathurin P, Kollinger M et al. In situ detection of lipid peroxidation in chronic hepatitis C: correlation with pathological features. J Clin Pathol 1997; 50: 401-406.
68. Cambiaggi C, Dominici S, Comporti M, Pompella A. Modulation of human T lymphocyte proliferation by 4-hydroxynonenal, the bioactive product of neutrophil-dependent lipid peroxidation. Life Sci 1997; 61: 777-785.
69. Requena JR, Fu MX, Ahmed MU et al. Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein. Biochem J 1997; 322: 317-325.
70. Chevion M, Berenshtein E, Stadtman ER. Human studies related to protein oxidation: protein carbonyl content as a marker of damage. Free Radic Res 2000; 33: S99-S108.
71. Winterbourn CC, Chan T, Buss IH, Inder TE, Mogridge N, Darlow BA. Protein carbonyls and lipid peroxidation products as oxidation markers in preterm infant plasma: associations with chronic lung disease and retinopathy and effects of selenium supplementation. Pediatr Res 2000; 48: 84-90.
72. De Cristofano R, Rocca B, Vitacolonna E et al. Lipid and protein oxidation contribute to a prothrombotic state in patients with type 2 diabetes mellitus. J Thromb Haemost 2003; 1: 250-256.
73. Chen S, Chang LS, Wei Y. Oxidative damage to proteins and decrease of antioxidant capacity in patients with varicocele. Free Radic Biol Med 2001; 30: 1328-1334.
74. Wardman P, von Sonntag C. Kinetic factors that control the fate of thiyl radicals in cells. Methods Enzymol 1995; 251: 31-45.
75. Prakash M, Upadhya S, Prabhu R. Protein thiol oxidation and lipid peroxidation in patients with uraemia. Scan J Clin Lab Invest 2004; 64: 599-604.
76. Fu S, Davies MJ, Stocker R, Dean RT. Evidence for roles of radicals in protein oxidation in advanced human atherosclerotic plaque. Biochem J 1998; 333: 519-525.
77. Silvester JA, Timmins GS, Davies MJ. Photodynamically generated bovine serum albumin radicals: evidence for damage transfer and oxidation at cysteine and tryptophan residues. Free Radic Biol Med 1998; 24: 754-766.
78. Funabiki R, Takeshita K, Miura Y, Shibasato M, Nagasawa T. Dietary supplement of G-rutin reduces oxidative damage in the rodent model. J Agric Food Chem 1999; 47: 1078-1082.
79. Srigiridhar K, Nair KM. Supplementation with alpha-tocopherol or a combination of alphatocopherol and ascorbic acid protects the gastrointestinal tract of iron-deficient rats against iron-induced oxidative damage during iron repletion. Br J Nutr 2000; 84: 165-173.
80. Adachi H, Ishii N. Effects of tocotrienols on life span and protein carbonylation in Caenorhabditis elegans. J Gerontol A Biol Sci Med Sci 2000; 55: B280-B285.
81. Porkkala-Sarataho E, Salonen JT, Nyyssonen K et al. Long-term effects of vitamin E, vitamin C, and combined supplementation on urinary 7-hydro-8-oxo-2′-deoxyguanosine, serum cholesterol oxidation products, and oxidation resistance of lipids in non-depleted men. Arterioscler Thromb Vasc Biol 2000; 20: 2087-2093.
82. Wander RC, Du SH. Oxidation of plasma proteins is not increased after supplementation with eicosapentaenoic and docosahexaenoic acids. Am J Clin Nutr 2000; 72: 731-737.
83. Garner B, Witting PK, Waldeck AR, Christison JK, Raftery M, Stocker R. Oxidation of high density lipoproteins. I. Formation of methionine sulfoxide in apolipoproteins AI and AII is an early event that accompanies lipid peroxidation and can be enhanced by alpha-tocopherol. J Biol Chem 1998; 273: 6080-6087.
84. Retsky KL, Chen K, Zeind J, Frei B. Inhibition of copper-induced LDL oxidation by vitamin C is associated with decreased copper-binding to LDL and 2-oxo-histidine formation. Free Radic Biol Med 1999; 26: 90-98.
85. Tsimikas S, Shortal BP, Witztum JL, Palinski W. In vivo uptake of radiolabeled MDA2, an oxidation-specific monoclonal antibody, provides an accurate measure of atherosclerotic lesions rich in oxidized LDL and is highly sensitive to their regression. Arterioscler Thromb Vasc Biol 2000; 20: 689-697.
86. Young JF, Dragsted LO, Daneshvar B, Lauridsen ST, Hansen M, Sandstrom B. The effect of grape-skin extract on oxidative status. Br J Nutr 2000; 84: 505-513.
87. Nielsen SE, Young JF, Daneshvar B et al. Effect of parsley (Petroselinum crispum) intake on urinary apigenin excretion, blood antioxidant enzymes and biomarkers for oxidative stress in human subjects. Br J Nutr 1999; 81: 447-455.
88. Gil L, Martínez G, González I et al. Effects of VIMANG on oxidative stress and marker of disease progression in HIV/AIDS patients. Free Radic Res 2002; 36: 107-109.
89. Williams MD, Remmen H, Conrad CC, Huang TT, Epstein CJ, Richardson A. Increased oxidative damage is correlated to altered mitochondrial function in heterozygous manganese superoxide dismutase knockout mice. J Biol Chem 1998; 273: 28510-28515.
90. Ingrosso D, D'angelo S, Carlo E, Perna AF, Zappia V, Galletti P. Increased methyl esterification of altered aspartyl residues in erythrocyte membrane proteins in response to oxidative stress. Eur J Biochem 2000; 267: 4397-4405.