Antioxidant activity of sulfur and selenium: A review of reactive oxygen species scavenging, glutathione peroxidase, and metal-binding antioxidant mechanisms

Cell Biochemistry and Biophysics

Volumn 55, Issue 1, 2009, Pages 1-23

  Battin, Erin E ^a   Brumaghim, Julia L ^a  

^a Chemistry Department   (United States)

Author keywords

Antioxidant mechanism; Glutathione peroxidase; Metal binding; Reactive oxygen species scavenging; Selenium antioxidants; Sulfur antioxidants

Indexed keywords

ANTIOXIDANT; FREE RADICAL; GLUTATHIONE PEROXIDASE; METAL; REACTIVE OXYGEN METABOLITE; SELENIUM; SULFUR;

APOPTOSIS; CHEMISTRY; METABOLISM; REVIEW;

ANTIOXIDANTS; APOPTOSIS; FREE RADICALS; GLUTATHIONE PEROXIDASE; METALS; REACTIVE OXYGEN SPECIES; SELENIUM; SULFUR;

EID: 67449102459     PISSN: 10859195     EISSN: None     Source Type: Journal    
DOI: 10.1007/s12013-009-9054-7     Document Type: Review

References (264)

1. Valko, M., Rhodes, C. J., Moncol, J., Izakovic, M., & Mazur, M. (2006). Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chemico-Biological Interactions,160, 1-40.
2. Cadet, J., Sage, E., & Douki, T. (2005). Ultraviolet radiation-mediated damage to cellular DNA. Mutation Research,571, 3-17.
3. Lloyd, D. R., Philips, D. H., & Carmichael, P. L. (1997). Generation of putative intrastrand cross-links and strand breaks in DNA by transition metal ion-mediated oxygen radical attack. Chemical Research in Toxicology,10, 393-400.
4. de Flora, S., & Izzotti, A. (2007). Mutagenesis and cardiovascular disease: Molecular mechanisms, risk factors, and protective factors. Mutation Research,621, 5-17.
5. Brewer, G. J. (2007). Iron and copper toxicity in diseases of aging, particularly atherosclerosis and Alzheimer's disease. Experimental Biology and Medicine,232, 323-335.
6. Angel, I., Bar, A., Horovitz, T., Taler, G., Krakovsky, M., Resnitsky, D., et al. (2002). Metal ion chelation in neurodegenerative disorders. Drug Development and Research,56, 300-309.
7. Perry, G., Cash, A. D., Srinivas, R., & Smith, M. A. (2002). Metals and oxidative homeostasis in Alzheimer's disease. Drug Development and Research,56, 293-299.
8. Stohs, S., & Bagchi, D. (1995). Oxidative mechanisms in the toxicity of metal ions. Free Radical Biology and Medicine,18, 321-336.
9. Park, S., & Imlay, J. A. (2003). High levels of intracellular cysteine promote oxidative DNA damage by driving the Fenton reaction. Journal of Bacteriology,185, 1942-1950.
10. Seifried, H. E., Anderson, D. E., Fisher, E. I., & Milner, J. A. (2007). A review of the interaction among dietary antioxidants and reactive oxygen species. Journal of Nutritional Biochemistry,18, 567-579.
11. Rice-Evans, C., Miller, N., & Paganga, G. (1997). Antioxidant properties of phenolic compound. Trends in Plant Science,2, 152-159.
12. Ramoutar, R. R., & Brumaghim, J. L. (2007). Effects of inorganic selenium compounds on oxidative DNA damage. Journal of Inorganic Biochemistry,101, 1028-1035.
13. Ramoutar, R. R., & Brumaghim, J. L. (2007). Investigating the antioxidant properties of oxo-sulfur compounds on metal-mediated DNA damage. Main Group Chemistry,6, 143-153.
14. Perron, N. R., Hodges, J. N., Jenkins, M., & Brumaghim, J. L. (2008). Predicting how polyphenol antioxidants prevent DNA damage by binding to iron. Inorganic Chemistry,47, 6153-6161.
15. Battin, E. E., Perron, N. R., & Brumaghim, J. L. (2006). The central role of metal coordination in selenium antioxidant activity. Inorganic Chemistry,45, 499-501.
16. Battin, E. E., & Brumaghim, J. L. (2008). Metal specificity in DNA damage prevention by sulfur antioxidants. Journal of Inorganic Biochemistry,102, 3036-3042.
17. Mates, J. M., Perez-Gomez, C., & Nunez de Castro, I. (1999). Antioxidant enzymes and human diseases. Clinical Biochemistry,32, 595-603.
18. Burton, G. W. (1990). Vitamin E: Antioxidant activity, biokinetics, and bioavailability. Annual Review of Nutrition,10, 357-382.
19. Padayatty, S. J., Katz, A., Wang, Y., Eck, P., Kwon, O., Lee, J.-H., et al. (2003). Vitamin C as an antioxidant: Evaluation of its role in disease prevention. Journal of the American College of Nutrition,22, 18-35.
20. Ames, B. N. (2001). DNA damage from micronutrient deficiencies is likely to be a major cause of cancer. Mutation Research,475, 7-20.
21. Cui, Y., Morgenstern, H., Greenland, S., Tashkin, D. P., Mao, J. T., Cai, L., et al. (2008). Dietary flavonoid intake and lung cancer: A population-based case-control study. Cancer,112, 2241-2248.
22. Erlund, I., Koli, R., Alfthan, G., Marniemi, J., Puukka, P., Mustonen, P., et al. (2008). Favorable effects of berry consumption on platelet function, blood pressure, and HDL cholesterol. American Journal of Clinical Nutrition,87, 323-331.
23. Carmeli, E., Bachar, A., Barchad, S., Morad, M., & Merrick, J. (2008). Antioxidant status in serum of persons with intellectual disability and hypothyroidism: A pilot study. Research on Developmental Disabilities,29, 431-438.
24. Resende, R., Moreira, P. I., Proenca, T., Deshpande, A., Busciglio, J., Pereira, C., et al. (2008). Brain oxidative stress in a triple-transgenic mouse model of Alzheimer disease. Free Radical Biology and Medicine,44, 2051-2057.
25. Chowdhury, R., Dutta, A., Chaudhuri, S. R., Sharma, N., Giri, A. K., & Chaudhuri, K. (2008). In vitro and in vivo reduction of sodium arsenite induced toxicity by aqueous garlic extract. Food and Chemical Toxicology,46, 740-751.
26. Seyedrezazadeh, E., Ostadrahimi, A., Mahboob, S., Assadi, Y., Ghaemmagami, J., & Pourmogaddam, M. (2008). Effect of vitamin E and selenium supplementation on oxidative stress status in pulmonary tuberculosis patients. Respirology,13, 294-298.
27. Mugesh, G., & Singh, H. B. (2000). Synthetic organoselenium compounds as antioxidants: Glutathione peroxidase activity. Chemical Society Reviews,29, 347-357.
28. Collins, C. A., Fry, F. H., Holme, A. L., Yiakouvaki, A., Al-Qenaei, A., Pourzand, C., et al. (2005). Toward multifunctional antioxidants: Synthesis, electrochemistry, in vitro and cell culture evaluation of compounds with ligand/catalytic properties. Organic and Biomolecular Chemistry,3, 1541-1546.
29. Halliwell, B. H., & Cross, C. E. (1994). Oxygen-derived species: Their relation to human disease and environmental stress. Environmental Health Perspectives,102, 5-12.
30. Halliwell, B. H., & Gutteridge, J. M. C. (1984). Oxygen toxicity, oxygen radicals, transition metals and disease. Biochemistry Journal,219, 1-14.
31. Thannickal, V. J., & Fanburg, B. L. (2000). Reactive oxygen species in cell signaling. American Journal of Physiology Lung Cellular and Molecular Physiology,279, L1005-L1028.
32. Goetz, M. E., & Luch, A. (2008). Reactive species: A cell damaging rout assisting to chemical carcinogens. Cancer Letters,266, 73-83.
33. Benov, L. (2001). How superoxide radical damages the cell. Protoplasma,217, 33-36.
34. Fridovich, I. (1983). Superoxide radical: An endogenous toxicant. Annual Review of Pharmacology and Toxicology,23, 239-257.
35. Ambrosone, C. B., Freudenheim, J. L., Thompson, P. A., Bowman, E., Vena, J. E., Marshall, J. R., et al. (1999). Manganese superoxide dismutase (MnSOD) genetic polymorphisms, dietary antioxidants, and risk of breast cancer. Cancer Research,59, 602-606.
36. Afonso, V., Champy, R., Mitrovic, D., Collin, P., & Lomri, A. (2007). Reactive oxygen species and superoxide dismutases: Role in joint diseases. Joint Bone Spine,74, 324-329.
37. Collin, B., Busseuil, D., Zeller, M., Perrin, C., Barthez, O., Duvillard, L., et al. (2007). Increased superoxide anion production is associated with early atherosclerosis and cardiovascular dysfunctions in a rabbit model. Molecular and Cellular Biochemistry,294, 225-235.
38. Waris, G., & Ahsan, H. (2006). Reactive oxygen species: Role in the development of cancer and various chronic conditions. Journal of Carcinogenesis,5, 1-8.
39. Lesko, S. A., Lorentzen, R. J., & Ts'o, P. O. P. (1980). Role of superoxide in deoxyribonucleic acid strand scission. Biochemistry,19, 3023-3028.
40. Keyer, K., & Imlay, J. A. (1996). Superoxide accelerates DNA damage by elevating free-iron levels. Proceedings of the National Academy of Science USA, 93, 13635-13640.
41. Zelko, I. N., Mariani, T. J., & Folz, R. J. (2002). Superoxide dismutases multigene family: A comparison of the CuZn-SOD (SOD1), Mn-SOD (SOD2), and EC-SOD (SOD3) gene structures, evolution, and expression. Free Radical Biology and Medicine,33, 337-349.
42. Keller, J. N., Kindy, M. S., Holtsber, F. W., St. Clair, D. K., Yen, H.-C., Germeyer, A., et al. (1998). Mitochondrial manganese superoxide dismutase prevents neural apoptosis and reduces ischemic brain injury: Suppression of peroxynitrite production, lipid peroxidation, and mitochondrial dysfunction. Journal of Neuroscience,18, 687-697.
43. Wang, P., Chen, H., Qin, H., Sankarapandi, S., Becher, M. W., Wong, P. C., & Zweier, J. L. (1998). Overexpression of human copper, zinc-superoxide dismutase (SOD1) prevents postischemic injury. Proceedings of the National Academy of Science USA, 95, 4556-4560.
44. Wheeler, M. D., Nakagami, M., Bradford, B. U., Uesugi, T., Mason, R. P., Connor, H. D., et al. (2001). Overexpression of manganese superoxide dismutase prevents alcohol-induced liver injury in the rat. Journal of Biological Chemistry,276, 36664-36672.
45. Potter, S. Z., & Valentine, J. S. (2003). The perplexing role of copper-zinc superoxide dismutase in amyotrophic lateral sclerosis (Lou Gehrig's disease). Journal of Biological Inorganic Chemistry,8, 373-380.
46. Tamai, M., Furuta, H., Kawashima, H., Doi, A., Hamanishi, T., Shimomura, H., et al. (2006). Extracellular superoxide dismutase gene polymorphism is associated with insulin resistance and the susceptibility to type 2 diabetes. Diabetes Research and Clinical Practice,71, 140-145.
47. Li, F., Calingasan, N. Y., Yu, F., Mauck, W. M., Toidze, M., Almeida, C. G., et al. (2004). Increased plaque burden in brains of APP mutant Mn SOD heterozygous knockout mice. Journal of Neurochemistry,89, 1308-1312.
48. Wheatley-Price, P., Asomaning, K., Reid, A., Zhai, R., Su, L., Zhou, W., et al. (2008). Myeloperoxidase and superoxide dismutase polymorphisms are associated with an increased risk of developing pancreatic adenocarcinoma. Cancer,112, 1037-1042.
49. Ergen, H. A., Narter, F., Timirci, O., & Isbir, T. (2007). Effects of manganese superoxide dismutase polymorphism, prediagnostic antioxidant status, and risk of clinical significant prostate cancer. Anticancer Research,27, 1227-1230.
50. Kowald, A., Lehrach, H., & Klipp, E. (2006). Alternative pathways as mechanism for the negative effects associated with overexpression of superoxide dismutase. Journal of Theoretical Biology,238, 828-840.
51. Noda, Y., Anzai, K., Mori, A., Kohno, M., Shinmei, M., & Packer, L. (1997). Hydroxyl and superoxide anion radical scavenging activities of natural source antioxidants using the computerized JES-FR30 ESR spectrometer system. Biochemistry and Molecular Biology International,42, 35-44.
52. White, C. R., Brock, T. A., Chang, L.-Y., Crapo, J., Briscoe, P., Ku, D., et al. (1994). Superoxide and peroxynitrite in atherosclerosis. Proceedings of the National Academy of Science USA, 91, 1044-1048.
53. Roussyn, I., Briviba, K., Masumoto, H., & Sies, H. (1996). Selenium-containing compounds protect DNA from single-single breaks caused by peroxynitrite. Archives of Biochemistry and Biophysics,330, 216-218.
54. Klotz, L.-O., & Sies, H. (2003). Defenses against peroxynitrite: Selenocompounds and flavonoids. Toxicology Letters,140, 125-132.
55. Bergendi, L., Benes, L., Durackova, Z., & Ferencik, M. (1999). Chemistry, physiology, and pathology of free radicals. Life Sciences,65, 1865-1874.
56. Davies, M. J. (2003). Singlet oxygen-mediated damage to proteins and its consequences. Biochemistry and Biophysics Research Communications,305, 761-770.
57. Young, I. S., & Woodside, J. V. (2001). Antioxidants in health and disease. Journal of Clinical Pathology,54, 176-186.
58. Plaetzer, K., Krammer, B., Berlanda, J., Berr, F., & Kiesslich, T. (2009). Photophysics and photochemistry of photodynamic therapy: Fundamental aspects. Lasers in Medical Science,24, 259-268.
59. Juarranz, A., Jaen, P., Sanz-Rodriguez, F., Cuevas, J., & Gonzalez, S. (2008). Photodynamic therapy of cancer: Basic principles, and applications. Cinical and Translational Oncology,10, 148-154.
60. Tan, D.-X., Manchester, L. C., Reiter, R. J., Plummer, B. F., Hardies, L. J., Weintraub, S. T., et al. (1998). A novel melatonin metabolite, cyclic 3-hydroxymelatonin: A biomarker of melatonin interaction with hydroxyl radicals. Biochemistry and Biophysics Research Communications,253, 614-620.
61. Halliwell, B., & Gutteridge, J. M. (1986). Oxygen lice radicals unit iron relation to biology and medicine: Some problems and concepts. Archives of Biochemistry and Biophysics,246, 501-514.
62. Bar-Or, D., Thomas, G. W., Rael, L. T., Lau, E. P., & Winkler, J. V. (2001). Asp-Ala-His-Lys (DAHK) inhibits copper-induced oxidative DNA double strand breaks and telomere shortening. Biochemistry and Biophysics Research Communications,282, 356-360.
63. Lippard, S. J., & Berg, J. M. (1994). Principles of Bioinorganic Chemistry (pp. 7-8). Mill Valley: University Science Books.
64. Beutler, E. (2007). Iron storage disease: Facts, fiction, and progress. Blood Cells, Molecules, and Diseases,39, 140-147.
65. Swaminathan, S., Fonseca, V. A., Alam, M. G., & Shah, S. V. (2007). The role of iron in diabetes and its complications. Diabetes Care,30, 1926-1933.
66. Schumman, K., Classen, H. G., Dieter, H. H., Konig, J., Multhaup, G., Rukgauer, M., et al. (2002). Hohenheim consensus workshop: Copper. European Journal of Clinical Nutrition,56, 469-483.
67. Reddy, M. B., & Clark, L. C. (2004). Iron, oxidative stress, and disease risk. Nutrition Reviews,62, 120-124.
68. Cooper, G. J. S., Chan, Y.-K., Dissanayake, A. M., Leahy, F. E., Koegh, G. F., Frampton, C. M., et al. (2005). Demonstration of a hyperglycemia-driven pathogenic abnormality of copper homeostasis in diabetes and its reversibility by selective chelation: Quantitative comparisons between the biology of copper and eight other nutritionally essential elements in normal and diabetic individuals. Diabetes,54, 1468-1476.
69. Ala, A., Walker, A. P., Ashkan, K., Dooley, J. S., & Schilsky, M. L. (2007). Wilson's disease. Lancet,369, 397-408.
70. Leone, N., Courbon, D., Ducimetiere, P., & Zureik, M. (2006). Zinc, copper, and magnesium and risks for all-cause, cancer, and cardiovascular mortality. Epidemiology,17, 308-314.
71. Trachootham, D., Lu, W., Ogasawara, M. A., Rivera-Del Valle, N., & Huang, P. (2008). Redox regulation of cell survival. Antioxidants and Redox Signaling,10, 1343-1374.
72. Meneghini, R. (1997). Iron homeostasis, oxidative stress, and DNA damage. Free Radical Biology and Medicine,23, 783-792.
73. Giles, N. M., Watts, A. B., Giles, G. I., Fry, F. H., Littlechild, J. A., & Jacob, C. (2003). Metal and redox modulation of cysteine protein function. Chemistry & Biology,10, 667-693.
74. Mzhel'skaya, T. I. (2000). Biological function of ceruloplasmin and their deficiency caused by mutation in genes regulating copper and iron metabolism. Bulletin of Experimental Biology and Medicine,130, 719-727.
75. Brumaghim, J. L., Li, Y., Henle, E., & Linn, S. (2003). Effects of hydrogen peroxide upon nicotinamide nucleotide metabolism in Escherichia coli: Changes in enzyme levels and nicotinamide nucleotide pools and studies of the oxidation of NAD(P)H by Fe(III). Journal of Biological Chemistry,278, 42495-42504.
76. Imlay, J. A., & Linn, S. (1986). Bimodal pattern of killing of DNA-repair-defective or anoxically grown Escherichia coli by hydrogen peroxide. Journal of Bacteriology,166, 519-527.
77. Imlay, J. A., & Linn, S. (1987). Mutagenesis and stress responses induced in Escherichia coli by hydrogen peroxide. Journal of Bacteriology,169, 2967-2976.
78. Mello-Filho, A. C., & Meneghini, R. (1991). Iron is the intracellular metal involved in the production of DNA damage by oxygen radicals. Mutation Research,251, 109-113.
79. Zhu, X., Su, B., Wang, X., Smith, M. A., & Perry, G. (2007). Causes of oxidative stress in Alzheimer disease. Cellular and Molecular Life Sciences,64, 2202-2210.
80. Ando, K., Ogawa, K., Misaki, S., & Kikugawa, K. (2002). Increased release of free Fe ions in human erythrocytes during aging and circulation. Free Radical Research,36, 1079-1084.
81. Berg, D., & Hochstrasser, H. (2006). Iron metabolism in Parkinsonian syndromes. Movement Disorders,21, 1299-1310.
82. Weinberg, E. D. (1999). Iron loading and disease surveillance. Emerging Infectious Diseases,5, 346-352.
83. Woodmansee, A. N., & Imlay, J. A. (2002). Quantitation of intracellular free iron by electron paramagnetic resonance spectroscopy. Methods in Enzymology,349, 3-9.
84. Messner, D. J., & Kowdley, K. V. (2008). Neoplastic transformation of rat liver epithelial cells is enhanced by non-transferrin-bound iron. BMC Gastroenterology,8, 1-10.
85. Shackelford, R. E., Manuszak, R. P., Johnson, C. D., Hellrung, D. J., Link, C. J., & Wang, S. (2004). Iron chelators increase the resistance of Ataxia telangeictasia cells to oxidative stress. DNA Repair,3, 1263-1272.
86. Prus, E., & Fibach, E. (2008). The labile iron pool in human erythroid cells. British Journal of Haematology,142, 301-307.
87. Lee, D.-H., Liu, D. Y., Jacobs, D. R., Jr., Shin, H.-R., Song, K., Lee, I.-K., et al. (2006). Common presence of non-transferrin-bound iron among patients with type 2 diabetes. Diabetes Care,29, 1090-1095.
88. Tuomainen, T.-P., Loft, S., Nyyssonen, K., Punnonen, K., Salonen, J. T., & Poulsen, H. E. (2007). Body iron is a contributor to oxidative damage of DNA. Free Radical Research,41, 324-328.
89. Evans, P. J., Smith, C., Mitchinson, M. J., & Halliwell, B. (1995). Metal ion release from mechanically-disrupted human arterial wall: Implications for the development of atherosclerosis. Free Radical Research,23, 465-469.
90. Gutteridge, J. M. C. (1986). Iron promoters of the Fenton reaction and lipid peroxidation can be released from haemoglobin by peroxides. FEBS Letters,201, 291-295.
91. White, B. C., Sullivan, J. M., DeGracia, D. J., O'Neil, B. J., Neumar, R. W., Grossman, L. I., et al. (2000). Brain ischemia and reperfusion: Molecular mechanisms of neuronal injury. Journal of Neurological Science,179, 1-33.
92. Brandolini, V., Tedeschi, P., Capece, A., Maietti, A., Mazzotta, D., Salzano, G., et al. (2002). Saccharomyces cerevisiae wine strains differing in copper resistance exhibit different capability to reduce copper content in wine. World Journal of Microbiology & Biotechnology,18, 499-503.
93. Que, E. L., Domaille, D. W., & Chang, C. J. (2008). Metals in neurobiology: Probing their chemistry and biology with molecular imaging. Chemical Reviews,108, 1517-1549.
94. Rae, T. D., Schmidt, P. J., Pufahl, R. A., Culotta, V. C., & O'Halloran, T. V. (1999). Undetectable intracellular free copper: The requirement of a copper chaperone for superoxide dismutase. Science,284, 805-808.
95. Yang, L., McRae, R., Henary, M. M., Patel, R., Lai, B., Vogt, S., et al. (2005). Imaging of the intracellular topography of copper with a fluorescent sensor and by synchrotron X-ray fluorescence microscopy. Proceedings of the National Academy of Science USA, 102, 11179-11184.
96. Miller, E. W., Zeng, L., Domaille, D. W., & Chang, C. J. (2006). Preparation and use of Coppersensor-1, a synthetic fluorophore for live-cell copper imaging. Nature Protocols,1, 824-827.
97. Reddy, P. V., Rama Rao, K. V., & Norenberg, M. D. (2008). The mitochondrial permeability transition, and oxidative and nitrosative stress in the mechanism of copper toxicity in cultured neurons and astrocytes. Laboratory Investigations,88, 816-830.
98. Mishra, O. P., Pooniya, V., Ali, Z., Upadhyay, R. S., & Prasad, R. (2008). Antioxidant status of children with acute renal failure. Pediatric Nephrology,23, 2047-2051.
99. Zappasodi, F., Salustri, C., Babiloni, C., Cassetta, E., Del Percio, C., Ercolani, M., et al. (2008). An observational study on the influence of the APOE-epsilon4 allele on the correlation between 'free' copper toxicosis and EEG activity in Alzheimer's disease. Brain Research,1215, 183-189.
100. Gupte, A., & Mumper, R. J. (2007). Copper chelation by D-penicillamine generates reactive oxygen species that are cytotoxic to human leukemia and breast cancer cells. Free Radical Biology and Medicine,43, 1271-1278.
101. Letavayova, L., Vlckova, V., & Brozmanova, J. (2006). Selenium: From cancer prevention to DNA damage. Toxicology,227, 1-14.
102. Brown, K. M., & Arthur, J. R. (2001). Selenium, selenoproteins, and human health: A review. Public Health and Nutrition,4, 593-599.
103. Kontoghiorghes, G. J., Efstathiou, A., Ioannou-Loucaides, S., & Kolnagou, A. (2008). Chelators controlling metal metabolism and toxicity pathways: Applications in cancer prevention, diagnosis, and treatment. Hemoglobin,32, 217-227.
104. Nielsen, P., Fischer, R., Buggisch, P., & Janka-Schaub, G. (2003). Effective treatment of hereditary haemochromatosis with desferrioxamine in selected cases. British Journal of Haematology,123, 952-953.
105. Hoffbrand, V. A., Cohen, A., & Hershko, C. (2003). Role of deferiprone in chelation therapy for transfusional iron overload. Blood,102, 17-24.
106. Richardson, D. R., & Ponka, P. (1998). Development of iron chelators to treat iron overload disease and their use as experimental tools to probe intracellular iron metabolism. American Journal of Hematology,58, 299-305.
107. Zheng, Y., Li, X.-K., Wang, Y., & Cai, L. (2008). The role of zinc, copper, and iron in the pathogenesis of diabetes and diabetic complications: Therapeutic effects by chelators. Hemoglobin,32, 135-145.
108. Miyoshi, K., Sugiura, Y., Ishizu, K., Iitaka, Y., & Nakamura, H. (1980). Glutathione-copper(II) complex with axial sulfur coordination and two copper sites via a disulfide bridge. Journal of the American Chemical Society,102, 6130-6136.
109. McAuliffe, C. A., Quagliano, J. V., & Vallarino, L. M. (1966). Metal complexes of the amino acid dl-methionine. Inorganic Chemistry,5, 1996-2003.
110. Sze, Y. K., Davis, A. R., & Neville, G. A. (1970). Raman and infrared studies of complexes of mercury(II) with cysteine, cysteine methyl ester, and methionine. Inorganic Chemistry,14, 1969-1974.
111. Shindo, H., & Brown, T. L. (1965). Infrared spectra of complexes of l-cysteine and related compounds with zinc(II), cadmium(II), mercury(II), and lead(II). Journal of the American Chemical Society,87, 1904-1909.
112. Livingstone, S. E., & Nolan, J. D. (1968). Metal chelates of biologically important compounds. I. Complexes of dl-methionine and S-methyl-l-cysteine. Inorganic Chemistry,7, 1447-1451.
113. Parcell, S. (2002). Sulfur in human nutrition and applications in medicine. Alternative Medicine Review,7, 22-44.
114. Atmaca, G. (2004). Antioxidant effects of sulfur-containing amino acids. Yonsei Medical Journal,45, 776-788.
115. Fleischauer, A. T., & Arab, L. (2001). Garlic and cancer: A critical review of the epidemiologic literature. Journal of Nutrition,131, 1032S-1040S.
116. Ip, C., & Ganther, H. E. (1992). Comparisons of selenium and sulfur analogs in cancer prevention. Carcinogenesis,13, 1167-1170.
117. Roediger, W. E. W., Moore, J., & Babidge, W. (1997). Colonic sulfide in pathogenesis and treatment of ulcerative colitis. Digestive Diseases and Sciences,42, 1571-1579.
118. Sha, S.-H., & Schacht, J. (2000). Antioxidants attenuate gentamicin-induced free radical formation in vitro and ototoxicity in vivo: d-methionine is a potential protectant. Hearing Research,142, 34-40.
119. Unnikrishnan, M. K., & Rao, M. N. A. (1990). Antiinflammatory activity of methionine, methionine sulfoxide, and methionine sulfone. Inflammation Research,31, 110-112.
120. Brosnan, J. T., & Brosnan, M. E. (2006). The sulfur-containing amino acids: An overview. Journal of Nutrition,136, 1636S-1640S.
121. Huang, D., Zhang, Y., Qi, Y., Chen, C., & Ji, W. (2008). Global DNA hypomethylation, rather than reactive oxygen species (ROS), a potential facilitator of cadmium-stimulated K562 cell proliferation. Toxicology Letters,179, 43-47.
122. Penugonda, S., Mare, S., Goldstein, G., Banks, W. A., & Ercal, N. (2005). Effects of N-acetylcysteine amide (NACA), a novel thiol antioxidant against glutamate-induced cytotoxicity in neuronal cell line PC12. Brain Research,1056, 132-138.
123. Delles, C., Miller, W. H., & Dominiczak, A. F. (2008). Targeting reactive oxygen species in hypertension. Antioxidants and Redox Signaling,10, 1061-1077.
124. Patrick, L. (2006). Lead toxicity part II: The role of free radical damage and the use of antioxidants in the pathology and treatment of lead toxicity. Alternative Medicine Review,11, 114-127.
125. Smith, C. V., Jones, D. P., Guenther, T. M., Lash, L. H., & Lauterburg, B. H. (1996). Compartmentation of glutathione: Implications for the study of toxicity and disease. Toxicology and Applied Pharmacology,140, 1-12.
126. Jones, D. P. (2006). Extracellular redox state: Refining the definition of oxidative stress in aging. Rejuvenation Research,9, 169-181.
127. Jones, D. P. (2006). Redefining oxidative stress. Antioxidants and Redox Signaling,8, 1865-1879.
128. Go, Y.-M., & Jones, D. P. (2005). Intracellular proatherogenic events and cell adhesion modulated by extracellular thiol/disulfide redox state. Circulation,111, 2973-2980.
129. Yildiz, G., & Demiryurek, A. T. (1998). Ferrous iron-induced luminol chemiluminescence: A method for hydroxyl radical study. Journal of Pharmacological and Toxicological Methods,39, 179-184.
130. Wassef, R., Haenold, R., Hansel, A., Brot, N., Heinemann, S. H., & Hoshi, T. (2007). Methionine sulfoxide reductase A and a dietary supplement S-methyl-L-cysteine prevent Parkinson's-like symptoms. Journal of Neuroscience,27, 12808-12816.
131. Ito, T., Kimura, Y., Uozumi, Y., Takai, M., Muraoka, S., Matsuda, T., et al. (2008). Taurine depletion caused by knocking out the taurine transporter gene leads to cardiomyopathy with cardiac atrophy. Journal of Molecular and Cellular Cardiology,44, 927-937.
132. Fotakis, G., & Timbrell, J. A. (2006). Modulation of cadmium chloride toxicity by sulphur amino acids in hepatoma cells. Toxicology in Vitro,20, 641-648.
133. de Melo Reis, R. A., Herculano, A. M., da Silva, M. C., dos Santos, R. M., & do Nascimento, J. L. (2007). In vitro toxicity induced by methylmercury on sympathetic neurons is reverted by l-cysteine or glutathione. Neuroscience Research,58, 278-284.
134. Cheung, P.-Y., Danial, H., Jong, J., & Schulz, R. (1998). Thiols protect the inhibition of myocardial aconitase by peroxynitrite. Archives of Biochemistry and Biophysics,350, 104-108.
135. Pfanzaql, B., Tribl, F., Koller, E., & Moslinger, T. (2003). Homocysteine strongly enhances metal-catalyzed LDL oxidation in the presence of cystine and cysteine. Atherosclerosis,168, 39-48.
136. Bendini, M. G., Lanza, G. A., Mazza, A., Giordano, A., Leggio, M., Menichini, G., et al. (2007). Risk factors for cardiovascular diseases: What is the role for homocysteine? Giornale Italiano di Cardiologia,8, 148-160.
137. Ceperkovic, Z. (2006). The role of increased levels of homocysteine in the development of cardiovascular diseases. Medicinski Pregled,59, 143-147.
138. Pezzini, A., Del Zotto, E., & Padovani, A. (2007). Homocysteine and cerebral ischemia: Pathogenic and therapeutic implications. Current Medicinal Chemistry,14, 249-263.
139. Venugopal, D., Zahid, M., Mailander, P. C., Meza, J. L., Rogan, E. G., Cavalieri, E. L., et al. (2008). Reduction of estrogen-induced transformation of mouse mammary epithelial cells by N-acetylcysteine. Journal of Steroid Biochemistry and Molecular Biology,109, 22-30.
140. Song, D., Hutchings, S., & Pang, C. C. (2005). Chronic N-acetylcysteine prevents fructose-induced insulin resistance and hypertension in rats. European Journal of Pharmacology,508, 205-210.
141. Breitkreutz, R., Pittack, N., Nebe, C. T., Schuster, D., Brust, J., Beichert, M., et al. (2000). Improvement of immune function in HIV infection by sulfur supplementation: Two randomized trials. Journal of Molecular Medicine,78, 55-62.
142. Ates, B., Abraham, L., & Ercal, N. (2008). Antioxidant and free radical scavenging properties of N-acetylcysteine amide (NACA) and comparison with N-acetylcysteine (NAC). Free Radical Research,42, 372-377.
143. Rooney, J. P. K. (2007). The role of thiols, dithiols, nutritional factors, and interacting ligands in the toxicology of mercury. Toxicology,234, 145-156.
144. Aposhian, H. V., Morgan, D. L., Queen, H. L. S., Maiorino, R. M., & Aposhian, M. M. (2003). Vitamin C, glutathione, or lipoic acid did not decrease brain or kidney mercuy in rats exposed to mercury vapor. Journal of Toxicology: Clincial Toxicology,41, 339-347.
145. Bridges, C. C., & Zalups, R. K. (2005). Molecular and ionic mimicry and the transport of toxic metals. Toxicology and Applied Pharmacology,204, 274-308.
146. Richardson, R. J., & Murphy, S. D. (1975). Effect of glutathione depletion on tissue deposition of methylmercury in rats. Toxicology and Applied Pharmacology,31, 505-519.
147. Powolny, A. A., & Singh, S. V. (2008). Multitargeted prevention and therapy of cancer by diallyl trisulfide and related Allium vegetable-derived organosulfur compounds. Cancer Letters,269, 305-314.
148. Kim, J. M., Chang, H. J., Kim, W. K., Chang, N., & Chun, H. S. (2006). Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds. Journal of Agricultural and Food Chemistry,54, 6547-6553.
149. Li, H., Li, H. Q., Wang, Y., Xu, H. X., Fan, W. T., Wang, M. L., et al. (2004). An intervention study to prevent gastric cancer by micro-selenium and large dose of allitridum. Chinese Medical Journal,117, 1155-1160.
150. Kaufmann, Y., Spring, P., & Klimberg, V. S. (2008). Oral glutamine prevents DMBA-induced mammary carcinogenesis via upregulation of glutathione production. Nutrition,24, 462-469.
151. Yeh, C.-C., Hou, M.-F., Wu, S.-H., Tsai, S.-M., Lin, S.-K., Hou, L. A., et al. (2006). A study of glutathione status in the blood and tissues of patients with breast cancer. Cell Biochemistry and Function,24, 555-559.
152. Estrela, J. M., Ortega, A., & Obrador, E. (2006). Glutathione in cancer biology and therapy. Critical Reviews in Clinical and Laboratory Science,43, 143-181.
153. Balendiran, G. K., Dabur, R., & Fraser, D. (2004). The role of glutathione in cancer. Cell Biochemistry and Function,22, 343-352.
154. Zeevalk, G. D., Razmpour, R., & Bernard, L. P. (2008). Glutathione and Parkinson's disease: Is this the elephant in the room? Biomedicine and Pharmacotherapy,62, 236-249.
155. Pensalfini, A., Cecchi, C., Zampagni, M., Becatti, M., Favilli, F., Paoli, P., et al. (2008). Protective effect of new S-acylglutathione derivatives against amyloid-induced oxidative stress. Free Radical Biology and Medicine,44, 1624-1636.
156. Bermejo, P., Martin-Aragon, S., Benedi, J., Susin, C., Felici, E., Gil, P., et al. (2008). Peripheral levels of glutathione and protein oxidation as markers in the development of Alzheimer's disease from mild cognitive impairment. Free Radical Research,42, 162-170.
157. Bharath, S., Cochran, B. C., Hsu, M., Liu, J., Ames, B. N., & Andersen, J. K. (2002). Pre-treatment with R-lipoic acid alleviates the effects of GSH depletion in PC12 cells: Implications for Parkinson's disease therapy. Neurotoxicology,23, 479-486.
158. Rezk, B. M., Haenen, G. R. M. M., van der Vijgh, W. J. F., & Bast, A. (2004). Lipoic acid protects efficiently only against a specific form of peroxynitrite-induced damage. Journal of Biological Chemistry,279, 9693-9697.
159. Risher, J. F., & Amler, S. N. (2005). Mercury exposure: Evaluation and intervention. The inappropriate use of chelating agents in the diagnosis and treatment of putative mercury poisoning. Neurotoxicology,26, 691-699.
160. Pinto, J. T., & Rivlin, R. S. (2001). Antiproliferative effects of allium derivatives from garlic. Journal of Nutrition,131, 1058S-1060S.
161. Shukla, Y., & Kalra, N. (2007). Cancer chemoprevention with garlic and its constituents. Cancer Letters,247, 167-181.
162. Kamada, K., Goto, S., Okunaga, T., Ihara, Y., Tsuji, K., Kawai, Y., et al. (2004). Nuclear glutathione S-transferase p prevents apoptosis by reducing the oxidative stress-induced formation of exocyclic DNA products. Free Radical Biology and Medicine,37, 1875-1884.
163. Molina-Holgado, F., Hider, R. C., Gaeta, A., Williams, R., & Francis, P. (2007). Metals, ions, and neurodegeneration. BioMetals,20, 639-654.
164. Willcox, J. K., Ash, S. L., & Catignani, G. L. (2004). Antioxidants and prevention of chronic disease. Critical Reviews in Food Science and Nutrition,44, 275-295.
165. Radi, R., Beckman, J. S., Bush, K. M., & Freeman, B. A. (1991). Peroxynitrite oxidation of sulfhydryls. The cytotoxic potential of superoxide and nitric oxide. Journal of Biological Chemistry,266, 4244-4250.
166. Karoui, H., Hogg, N., Frejaville, C., Tordo, P., & Kalyanaraman, B. (1996). Characterization of sulfur-centered radical intermediates formed during the oxidation of thiols and sulfite by peroxynitrite. ESR-spin trapping and oxygen uptake studies. Journal of Biological Chemistry,271, 6000-6009.
167. Briviba, K., Roussyn, I., Sharov, V. S., & Sies, H. (1996). Attenuation of oxidation and nitration reactions of peroxynitrite by selenomethionine, selenocysteine and ebselen. Biochemical Journal,319, 13-15.
168. Whiteman, M., & Halliwell, B. (1997). Thiols and disulfides can aggravate peroxynitrite-dependent inactiviation of alpha-1-antiproteinase. FEBS Letters,414, 497-500.
169. Reist, M., Marshall, K.-A., Jenner, P., & Halliwell, B. (1998). Toxic effects of sulfite in combination with peroxynitrite on neuronal cells. Journal of Neurochemistry,71, 2431-2438.
170. Nakagawa, H., Sumiki, E., Takusagawa, M., Ikota, N., Matsushima, Y., & Ozawa, T. (2000). Scavengers for peroxynitrite: Inhibition of tyrosine nitration and oxidation with tryptamine derivatives, alpha-lipoic acid and synthetic compounds. Chemical and Pharmaceutical Bulletin,48, 261-265.
171. Giles, G. I., Tasker, K. M., & Jacob, C. (2001). Hypothesis: The role of reactive sulfur species in oxidative stress. Free Radical Biology and Medicine,31, 1279-1283.
172. Giles, G. I., & Jacob, C. (2002). Reactive sulfur species: An emerging concept in oxidative stress. Biological Chemistry,383, 375-388.
173. Anwar, A., Burkholz, T., Scherer, C., Abbas, M., Lehr, C.-M., Diederich, M., et al. (2008). Naturally occurring reactive sulfur species, their activity against Caco-2 cells, and possible modes of biochemical action. Journal of Sulfur Chemistry,29, 251-268.
174. Wiseman, A. (2004). Dietary alkyl thiol free radicals (RSS) can be as toxic as reactive oxygen species (ROS). Medical Hypotheses,63, 667-670.
175. Jacob, C., & Lancaster, J. R. G. G. I. (2004). Reactive sulphur species in oxidative signal transduction. Biochemical Society Transactions,32, 1015-1017.
176. Nagy, P., Becker, J. D., Mallo, R. C., & Ashby, M. T. (2007). The Jekyll and Hyde roles of cysteine derivatives during oxidative stress. ACS Symposium Series, 967 (New Biocides Development), 193-212.
177. Nagy, P., Lemma, K., & Ashby, M. T. (2007). Reactive sulfur species: Kinetics and mechanisms of the reaction of cysteine thiosulfinate ester with cysteine to give cysteine sulfenic acid. Journal of Organic Chemistry,72, 8838-8846.
178. Wang, X., & Ashby, M. T. (2008). Reactive sulfur species: Kinetics and mechanism of the reaction of thiocarbamate-S-oxide with cysteine. Chemical Research in Toxicology,21, 2120-2126.
179. Quig, D. (1998). Cysteine metabolism and metal toxicity. Alternative Medicine Review,3, 262-270.
180. Waalkes, M. P., Liu, J., Goyer, R. A., & Diwan, B. A. (2004). Metallothionein-I/II double knockout mice are hypersensitive to lead-induced kidney carcinogenesis. Cancer Research,64, 7766-7772.
181. Liu, J., Liu, Y., Habeebu, S. M., Waalkes, M. P., & Klaasen, C. D. (2000). Chronic combined exposure to cadmium and arsenic exacerbates nephrotoxicity, particularly in metallothionein-I/II null mice. Toxicology,147, 157-166.
182. You, H. J., Lee, K. J., & Jeong, H. G. (2002). Overexpression of human metallothionein-III prevents hydrogen peroxide-induced oxidative stress in human fibroblasts. FEBS Letters,521, 175-179.
183. Presta, A., Green, A. R., Zelazowki, A., & Stillman, M. J. (1995). Copper binding to rabbit liver metallothionein. European Journal of Biochemistry,227, 226-240.
184. Jacob, C., Giles, G. I., Giles, N. M., & Sies, H. (2003). Sulfur and selenium: The role of oxidation state in protein structure and function. Angewandte Chemie. International Edition,42, 4742-4758.
185. Singhal, R. K., Anderson, M. E., & Meister, A. (1987). Glutathione, a first line of defense against cadmium toxicity. FASEB Journal,1, 220-223.
186. Foster, L. H. (1995). Selenium in the environment, food, and health. Nutrition and Food Science, 95, 17-23.
187. Hawkes, W. C., Richter, B. D., Alkan, Z., Souza, E. C., Derricote, M., Mackey, B. E., et al. (2008). Response of selenium status indicators to supplementation of healthy north American men with high-selenium yeast. Biological Trace Element Research,122, 107-121.
188. Morris, V. C. & Levaner, O. A. (1970). Selenium content in foods. Journal of Nutrition, 100, 1383-1388.
189. Diwadkar-Navsariwala, V., Prins, G. S., Swanson, S. M., Birch, L. A., Ray, V. H., Hedayat, S., et al. (2006). Selenoprotein deficiency accelerates prostate carcinogenesis in a transgenic model. Proceedings of the National Academy of Science,103, 8179-8184.
190. Diwadkar-Navsariwala, V., & Diamond, A. M. (2004). The link between selenium and chemoprevention: A case for selenoproteins. Journal of Nutrition,134, 2899-2902.
191. Tapiero, H., Townsend, D. M., & Tew, K. D. (2003). The antioxidant role of selenium and seleno-compounds. Biomedicine & Pharmacotherapy,57, 134-144.
192. Papp, L. V., Lu, J., Holmgren, A., & Khanna, K. K. (2007). From selenium to selenoproteins: Synthesis, identity, and their role in human health. Antioxidants and Redox Signaling,9, 775-806.
193. Lee, C. Y., Hsu, Y. C., Wang, J. Y., Chen, C. C., & Chiu, J. H. (2008). Chemopreventivie effect of selenium and Chinese medicinal herbs on N-nitrosobis(2-oxopropyl)amine-induced hepatocellular carcinoma in Syrian hamsters. Liver International,28, 841-855.
194. Mugesh, G., Panda, A., Singh, H. B., Punekar, N. S., & Butcher, R. J. (2001). Glutathione peroxidase-like antioxidant activity of diaryl diselenides: A mechanistic study. Journal of the American Chemical Society,123, 839-850.
195. Whanger, P. D. (2002). Selenocompounds in plants and animals and their biological significance. Journal of American College of Nutrition,21, 223-232.
196. Kumar, B., Nahreini, P., Hanson, A. J., Andreatta, C., Prasad, J. E., & Prasad, K. N. (2005). Selenomethionine prevents degeneration induced by overexpression of wild-type human synuclein during differentiation of neuroblastoma cells. Journal of the American College of Nutrition,24, 516-523.
197. De Silva, V., Woznichak, M. M., Burns, K. L., Grant, K. B., & May, S. W. (2004). Selenium redox cycling in the protective effects of organoselenides against oxidant-induced DNA damage. Journal of the American Chemical Society,126, 2409-2413.
198. Battin, E. E. & Brumaghim, J. L. Preventing metal-mediated oxidative DNA damage with selenium compounds. submitted.
199. Cao, T. H., Cooney, R. A., Woznichak, M. M., May, S. W., & Browner, R. F. (2001). Speciation and identification of organoselenium metabolites in human urine using inductively coupled plasma mass spectrometry and tandem mass spectrometry. Analytical Chemistry,73, 2898-2902.
200. Yasuda, K., Watanabe, H., Yamazaki, S., & Toda, S. (1980). Glutathione peroxidase activity of d, l-selenocysteine and selenocystamine. Biochemistry and Biophysics Research Communications,96, 243-249.
201. Schrauzer, G. N. (2000). Selenomethionine: A review of its nutritional significance, metabolism and toxicity. Journal of Nutrition,130, 1653-1656.
202. Kunwar, A., Mishra, B., Barik, A., Kumbhare, L. B., Pandey, R., Jain, V. K., et al. (2007). 3, 3-Diselenodipropionic acid, an efficient peroxyl radical scavenger and a GPx mimic, protects erythrocytes (RBCs) from AAPH-induced hemolysis. Chemical Research in Toxicology,20, 1482-1487.
203. Fan, A. M., & Kizer, K. W. (1990). Selenium: Nutritional, toxicologic and clinical aspects. Western Journal of Medicine,153, 160-167.
204. Ostadalova, I., Vobecky, M., Chvojkova, Z., Mikova, D., Hampl, V., Wilhelm, J., et al. (2007). Selenium protects the immature rat heart against ischemia/reperfusion injury. Molecular and Cellular Biochemistry,300, 259-267.
205. Toufektsian, M.-C., Boucher, F., Pucheu, S., Tanguy, S., Ribuot, C., Sanou, D., et al. (2000). Effects of selenium deficiency on the response of cardiac tissue to ischemia and reperfusion. Toxicology,148, 125-132.
206. Suzuki Kazuo, T., Yuki, O., & Suzuki, N. (2006). Availability and metabolism of 77Se-methylseleninic acid compared simultaneously with those of three related selenocompounds. Toxicology and Applied Pharmacology,217, 51-62.
207. Baljinnyam, E., Hasebe, N., Morihira, M., Sumitomo, K., Matsusaka, T., Fujino, T., et al. (2006). Oral pretreatment with ebselen enhances heat shock protein 72 expression and reduced myocardial infarct size. Hypertension Research,29, 905-913.
208. Imai, H., Graham, D. I., Masayasu, H., & Macrae, I. M. (2003). Antioxidant ebselen reduces oxidative damage in focal cerebral ischemia. Free Radical Biology and Medicine,34, 56-63.
209. Li, Y., & Cao, Z. (2002). The neuroprotectant ebselen inhibits oxidative DNA damage induced by dopamine in the presence of copper ions. Neuroscience Letters,330, 69-73.
210. Yamaguchi, T., Sano, K., Takakura, K., Saito, I., Shinohara, Y., Asano, T., et al. (1998). Ebselen in acute ischemic stroke: A placebo-controlled, double-blind clinical trial. Ebselen Study Group. Stroke,29, 12-17.
211. Takahashi, H., Nishina, A., Fukumoto, R. H., Kimura, H., Koketsu, M., & Ishihara, H. (2005). Selenocarbamates are effective superoxide anion scavengers in vitro. European Journal of Pharmaceutical Sciences,24, 291-295.
212. Whanger, P. D. (2004). Selenium and its relationship to cancer: An update. British Journal of Nutrition,91, 11-28.
213. Xiong, S., Markesbery, W. R., Shao, C., & Lovell, M. A. (2007). Seleno-l-methionine protects against beta-amyloid and iron/hydrogen peroxide-mediated neuron death. Antioxidants and Redox Signaling,9, 457-467.
214. Clark, L. C., Combs, G. F., Jr., Turnbull, B. W., Slate, E. H., Chalker, D. K., Chow, J., et al. (1996). Effects of selenium supplementation for cancer prevention in patients with carcinoma of the skin. A randomized controlled trial. Nutritional Prevention of Cancer Study Group. Journal of the American Medical Association,276, 1957-1963.
215. Klein, E. A., Lippman, S. M., Thompson, I. M., Goodman, P. J., Albanes, D., Taylor, P. R., et al. (2003). The selenium and vitamin E cancer prevention trial. World Journal of Urology,21, 21-27.
216. Bleys, J., Navas-Acien, A., & Guallar, E. (2008). Serum selenium levels and all-cause, cancer, and cardiovascular mortality among US adults. Archives of Internal Medicine,168, 404-410.
217. Combs, G. F., Jr., & Gray, W. P. (1998). Chemopreventive agents: Selenium. Pharmacology and Therapeutics,79, 179-192.
218. Gromadzinska, J., Reszka, E., Bruzelius, K., Wasowicz, W., & Akesson, B. (2008). Selenium and cancer: Biomarkers of selenium status and molecular action of selenium supplements. European Journal of Nutrition,47, 29-50.
219. Kellen, E., Zeegers, M., & Buntinx, F. (2006). Selenium is inversely associated with bladder cancer risk: A report from the Belgian case-control study on bladder cancer. International Journal of Urology,13, 1180-1184.
220. Zuo, X. L., Chen, J. M., Zhou, X., Li, X. Z., & Mei, G. Y. (2006). Levels of selenium, zinc, copper, and antioxidant enzyme activity in patients with leukemia. Biological Trace Element Research,114, 41-53.
221. Ozgen, I. T., Dagdemir, A., Elli, M., Saraymen, R., Pinarli, F. G., Fisqin, T., et al. (2007). Hair selenium status in children with leukemia and lymphoma. Journal of Pediatric Hematology/oncology,29, 519-522.
222. Musil, F., Zadak, Z., Solichova, D., Hyspler, R., Kaska, M., Sobotka, L., et al. (2005). Dynamics of antioxidants in patients with acute pancreatitis and in patients operated for colorectal cancer: A clinical study. Nutrition,21, 118-124.
223. Moradi, M., Hassan Eftekhari, M., Talei, A., & Rajaei Fard, A. (2009). A comparative study of selenium concentration and glutathione peroxidase activity in normal and breast cancer patients. Public Health and Nutrition,12, 59-63.
224. Fuyu, Y. (2006). Keshan disease and mitochondrial cardiomyopathy. Science in China Series C: Life Sciences,49, 513-518.
225. Burk, R. F. (2002). Selenium, an antioxidant nutrient. Nutrition and Clinical Care,5, 75-79.
226. Kosar, F., Sahin, I., Acikgoz, N., Aksoy, Y., Kucukbay, Z., & Cehreli, S. (2005). Significance of serum trace element status in patients with rheumatic heart disease: A prospective study. Biological Trace Element Research,107, 1-10.
227. Nawrot, T. S., Staessen, J. A., Roels, H. A., Hond, E. D., Lutgarde, T., Fargard, R. H., et al. (2007). Blood pressure and blood selenium: A cross-sectional and longitudinal population study. European Heart Journal,28, 628-633.
228. Flores-Mateo, G., Navas-Acien, A., Pastor-Barriuso, R., & Guallar, E. (2006). Selenium and coronary heart disease: A meta-analysis. American Journal of Clinical Nutrition,84, 762-773.
229. Ashrafi, M. R., Shams, S., Nouri, M., Mohseni, M., Shabanian, R., Rekaninejad, M. S., et al. (2007). A probable causative factor for an old problem: Selenium and glutathione peroxidase appear to play important roles in epilepsy pathogenesis. Epilepsia,48, 1750-1755.
230. Akbaraly, N. T., Hininger-Favier, I., Carriere, I., Arnaud, J., Gourlet, V., Roussel, A. M., et al. (2007). Plasma selenium over time and cognitive decline in the elderly. Epidemiology,18, 52-58.
231. Chen, J. M., & Berry, M. J. (2003). Selenium and selenoproteins in the brain and brain diseases. Journal of Neurochemistry,86, 1-12.
232. Wenstrup, D., Ehmann, W. D., & Markesbery, W. R. (1990). Trace element imbalances in isolated subcellular fractions of Alzheimer's disease brains. Brain Research,533, 125-131.
233. Cornett, C. R., Markesbery, W. R., & Ehmann, W. D. (1998). Imbalances of trace elements related to oxidative damage in Alzheimer's disease brain. Neurotoxicology,19, 339-345.
234. Ceballos-Picot, I., Merad-Boudia, M., Nicole, A., Thevenin, M., Hellier, G., Legrain, S., et al. (1996). Peripheral antioxidant enzyme activities and selenium in elderly subjects and in dementia of Alzheimer's type: Pace of the extracellular glutathione peroxidase. Free Radical Biology and Medicine,20, 579-587.
235. Clausen, J., Jensen, G. E., & Nielsen, S. A. (1988). Selenium in chronic neurologic diseases, multiple sclerosis, Batten's disease. Biological Trace Element Research,15, 179-203.
236. Aguilar, M. V., Jimenez-Jimenez, F. J., Molina, J. A., Meseguer, I., Mateos-Vega, C. J., Gonzalez-Munoz, M. J., et al. (1998). Cerebrospinal fluid selenium and chromium levels in patients with Parkinson's disease. Journal of Neural Transmission,105, 1245-1251.
237. Meseguer, I., Molina, J. A., Jimenez-Jimenez, F. J., Aguilar, M. V., Mateos-Vega, C. J., Gonzalez-Munoz, M. J., et al. (1999). Cerebrospinal fluid levels of selenium in patients with Alzheimer's disease. Journal of Neural Transmission,106, 309-315.
238. Takahashi, H., Nishina, A., Fukumoto, R. H., Kimura, H., Koketsu, M., & Ishihara, H. (2005). Selenoureas and thioureas are effective superoxide radical scavengers in vitro. Life Sciences,76, 2185-2192.
239. Laude, K., Thuillez, C., & Richard, V. (2002). Peroxynitrite triggers a delayed resistance of coronary endothelial cells against ischemia-reperfusion injury. American Journal of Physiology Heart and Circulatory Physiology,283, H1418-H1423.
240. Sies, H., & Arteel, G. E. (2000). Interaction of peroxynitrite with selenoproteins and glutathione peroxidase mimics. Free Radical Biology and Medicine,28, 1451-1455.
241. Trujillo, M., Ferrer-Sueta, G., & Radi, R. (2008). Peroxynitrite detoxification and its biologic implications. Antioxidants and Redox Signaling,10, 1607-1620.
242. Klotz, L.-O., Kroncke, K.-D., Buchczyk, D. P., & Sies, H. (2003). Role of copper, zinc, selenium and tellurium in the cellular defense against oxidative and nitrosative stress. Journal of Nutrition,133, 1448S-1451S.
243. Sies, H. & Arteel, G. E. (2003). Strategies for controlling oxidative stress: Protection against peroxynitrite and hydroperoxides by selenoproteins and selenoorganic compounds. Critical Reviews of Oxidative Stress and Aging, 2.
244. Fang, Y.-A., Yang, S., & Wu, G. (2002). Free radicals, antioxidants, and nutrition. Nutrition,18, 872-879.
245. Mugesh, G., & Singh, H. B. (2000). Biological activities of synthetic organoselenium compounds: Recent developments. Proceedings of National Academic Science, India, Section A: Physical Sciences,70, 207-220.
246. Giles, G. I., Fry, F. H., Tasker, K. M., Holme, A. L., Peers, C., Green, K. N., et al. (2003). Evaluation of sulfur, selenium and tellurium catalysts with antioxidant potential. Organic & Biomolecular Chemistry,1, 4317-4322.
247. Chang, T.-C., Huang, M.-L., Hsu, W.-L., Hwang, J.-M., & Hsu, L.-Y. (2003). Synthesis and biological evaluation of ebselen and its acyclic derivatives. Chemical and Pharmaceutical Bulletin,51, 1213-1416.
248. Lin, C.-F., Chang, T.-C., Chiang, C.-C., Tsai, H.-J., & Hsu, L.-Y. (2005). Synthesis of selenium-containing polyphenolic acid esters and evaluation of their effects on antioxidation and 5-lipoxygenase inhibition. Chemical and Pharmaceutical Bulletin,53, 1402-1407.
249. Mugesh, G., du Mont, W.-W., & Sies, H. (2001). Chemistry of biologically important synthetic organoselenium compounds. Chemical Reviews,101, 2125-2180.
250. Wilson, S. R., Zucker, P. A., Huang, R.-R. C., & Spector, A. (1989). Development of synthetic compounds with glutathione peroxidase activity. Journal of the American Chemical Society,111, 5936-5939.
251. Stadtman, T. C. (2006). Selenium biochemistry: Mammalian selenoenzymes. Annals of the New York Academy of Sciences,899, 399-402.
252. Mugesh, G., Panda, A., Singh, H. B., Punekar, N. S., & Butcher, R. J. (1998). Diferrocenyl diselenides: Excellent thiol peroxidase-like antioxidants. Chemical Communications,222, 7-2228.
253. Mishra, B., Priyadarsini, K. I., Mohan, H., & Mugesh, G. (2006). Horseradish peroxidase inhibition and antioxidant activity of ebselen and related organoselenium compounds. Bioorganic & Medicinal Chemistry Letters,16, 5334-5338.
254. Sarma, B., & Mugesh, G. (2005). Glutathione peroxidase (GPx)-like antioxidant activity of the organoselenium drug ebselen: Unexpected complications with thiol exchange reactions. Journal of the American Chemical Society,127, 11477-11485.
255. Mareque, A. M.-M., Faez, J. M., Chistiaens, L., Kohnen, S., Deby, C., Hoebeke, M., et al. (2004). In vitro evaluation of glutathione peroxidase (GPx)-like activity and antioxidant properties of some ebselen analogues. Redox Report,9, 81-87.
256. Mishra, B., Barik, A., Kunwar, A., Kumbhare, L. B., Priyadarsini, K. I., & Jain, V. K. (2008). Correlating the GPx activity of selenocystine derivatives with one-electron redox reactions. Phosphorus Sulfur Silicon,183, 1018-1025.
257. Marnett, L. J. (2000). Oxyradicals and DNA damage. Carcinogenesis,21, 361-370.
258. 4 cluster. Science,275, 1305-1307.
259. Garcin, E., Vernede, X., Hatchikian, E. C., Volbeda, A., Frey, M., & Fontecillia-Camps, J. C. (1999). The crystal structure of a reduced [NiFeSe] hydrogenase provides an image of the activated catalytic center. Structure,7, 557-566.
260. Zainal, H. A., & Wolf, W. R. (1995). Potentiometric and spectroscopic study of selenomethionine complexes with copper(II) and zinc(II) ions. Transition Metal Chemistry,20, 225-227.
261. Goulet, A.-C., Chigbrow, M., Frisk, P., & Nelson, M. A. (2005). Selenomethionine induces sustained ERK phosphorylation leading to cell-cycle arrest in human colon cancer cells. Carcinogenesis, 26, 109-117.
262. Zachara, B. A., Trafikowska, U., Adamowicz, A., Nartowicz, E., & Manitius, J. (2001). Selenium, glutathione peroxidases, and some other antioxidant parameters in blood of patients with chronic renal failure. Journal of Trace Elements in Medicine and Biology, 15, 161-166.
263. Wetli, H. A., Buckett, P. D., & Wessling-Resnick, M. (2006). Small-molecule screening identifies the selanazal drug ebselen as a potent inhibitor of DMT1-mediated iron uptake. Chemistry & Biology,13, 965-972.
264. Oikawa, T., Esaki, N., Tanaka, H. & Soda, K. (1991). Metalloselenonein, the selenium analogue of metallothionein: Synthesis and characterization of its complex with copper ions. Proceedings of the National Academy of Science USA, 88, 3057-3059.