Protective Effect of the Xanthate, D609, on Alzheimer's Amyloid β-peptide (1–42)-induced Oxidative Stress in Primary Neuronal Cells

References

• Yankner, BA. (2000) "The pathogenesis of Alzheimer's disease. Is amyloid beta-protein the beginning or the end?", Ann. N.Y. Acad. Sci. 924, 26–28.
   PubMedGoogle Scholar
• Cotman, C.W. (1998) "Apoptosis decision cascades and neuronal degeneration in Alzheimer's disease", Neurobiol. Aging 19, S29–532.
   Google Scholar
• Mattson, M.P. and Mattson, E.P. (2002) "Amyloid peptide enhances nail rusting: novel insight into mechanisms of aging and Alzheimer's disease", Ageing Res. Rev. 1, 327–330.
   PubMedGoogle Scholar
• Varadarajan, S., Yatin, S., Aksenova, M. and Butterfield, D.A. (2000) "Review: Alzheimer's amyloid beta-peptide-associ-ated free radical oxidative stress and neurotoxicity", J. Struct. Biol. 130, 184–208.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A. (2002) "Amyloid beta-peptide (1-42)-induced oxidative stress and neurotoxicity:implications for neurodegeneration in Alzheimer's disease brain. A review", Free Radic. Res. 36, 1307–1313.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A. and Lauderback, C.M. (2002) "Lipid peroxidation and protein oxidation in Alzheimer's disease brain: potential causes and consequences involvingamyloid b-peptide-associated free radical oxidative stress", Free Radic. Biol. Med. 32, 1050–1060.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A., Drake, J., Pocernich, C. and Castegna, A. (2001) "Evidence of oxidative damage in Alzheimer's disease brain: central role for amyloid beta-peptide", Trends Mol. Med. 7, 548–554.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A., Castegna, A., Lauderback, C.M. and Drake, J. (2002a) "Evidence that amyloid beta-peptide-induced lipid peroxidation and its sequelae in Alzheimer's disease brain contribute to neuronal death", Neurobiol. Aging 23, 655–664.
   PubMed Web of Science ®Google Scholar
• Bains, J.S. and Shaw, C.A. (1997) "Neurodegenerative disorders in humans: the role of glutathione in oxidative stress mediated neuronal death", Brain Res. Rev. 25, 335–358.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A. and Kanski, J. (2001) "Brain protein oxidation in age-related neurodegenerative disorders that are associated with aggregated proteins", Mech. Ageing Dev. 122, 945–962.
   PubMed Web of Science ®Google Scholar
• Wullner, U., Seyfried, J., Groscurth, P., Beinroth, S., Winter, S., Gleichmarm, M., Heneka, M., Loschmann, P., Schulz, J.B., Weller, M. and Klockgether, T. (1999) "Glutathione depletion and neuronal cell death: the role of reactive oxygen intermediates and mitochondrial function", Brain Res. 826, 53–62.
   PubMed Web of Science ®Google Scholar
• Schulz, J.B., Lindenau, J., Seyfried, J. and Dichgans, J. (2000) "Glutathione, oxidative stress and neurodegeneration", Fur. J. Biochem. 267, 4904–4911.
   Google Scholar
• Benzi, G. and Moretti, A. (1995) "Age- and peroxidative stress-related modifications of the cerebral enzymatic activities linked to mitochondria and the glutathione system", Free Radic. Biol. Med. 19, 77–101.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A. (1997) "beta-Amyloid-associated free radical oxidative stress and neurotoxicity: implications for Alzhei-mer's disease", Chem. Res. Toxicol. 10, 495–506.
   PubMed Web of Science ®Google Scholar
• Markesbery, W.R. (1997) "Oxidative stress hypothesis in Alzheimer's disease", Free Radic. Biol. Med. 23, 134–147.
   PubMed Web of Science ®Google Scholar
• Butterfield, D., Castegna, A., Pocernich, C., Drake, J., Scapagnini, G. and Calabrese, V. (2002) "Nutritional approaches to combat oxidative stress in Alzheimer's disease", J. Nutr. Biochem. 13, 444.
   PubMed Web of Science ®Google Scholar
• Halliwell, B. (2001) "Role of free radicals in the neurodegen-erative diseases: therapeutic implications for antioxidant treatment", Drugs Aging 18, 685–716.
   PubMed Web of Science ®Google Scholar
• Anderson, M.E. and Luo, J.L. (1998) "Glutathione therapy: from prodrugs to genes", Semin. Liver Dis. 18, 415–424.
   PubMed Web of Science ®Google Scholar
• Drake, J., Kanski, J., Varadarajan, S., Tsoras, M. and Butterfield, D.A. (2002) "Elevation of brain glutathione by gamma-glutamylcysteine ethyl ester protects against peroxynitrite-induced oxidative stress", J. Neurosci. Res. 68, 776–784.
   PubMed Web of Science ®Google Scholar
• Drake, J., Sultana, R., Aksenova, M., Calabrese, V. and Butterfield, D.A. (2003) "Elevation of mitochondrial gluta-thione by gamma-glutamylcysteine ethyl ester protects mitochondria against peroxynitrite-induced oxidative stress", J. Neurosci. Res. 74, 917–927.
   PubMed Web of Science ®Google Scholar
• Pocernich, C.B., Cardin, A.L., Racine, C.L., Lauderback, C.M. and Butterfield, D.A. (2001) "Glutathione elevation and its protective role in acrolein-induced protein damage in synaptosomal membranes: relevance to brain lipid pero)d-dation in neurodegenerative disease", Neurochem. Int. 39, 141–149.
   PubMed Web of Science ®Google Scholar
• Levy, E.J., Anderson, M.E. and Meister, A. (1994) "Preparation and properties of glutathione diethyl ester and related derivatives", Methods Enzymol. 234, 499–504.
   PubMedGoogle Scholar
• Lauderback, C.M., Drake, J., Zhou, D., Hackett, J.M., Castegna, A., Kanski, J., Tsoras, M., Varadarajan, S. and Butterfield, D.A. (2003) "Derivatives of xanthic acid are novel antioxidants: application to synaptosomes", Free Radic. Res. 37, 355–365.
   PubMed Web of Science ®Google Scholar
• Sauer, G., Amtmarm, E., Melber, K., Knapp, A., Muller, K., Hummel, K. and Scherm, A. (1984) "DNA and RNA virus species are inhibited by xanthates, a class of antiviral compounds with unique properties", Proc. Natl Acad. Sci. LISA 81, 3263–3267.
   PubMed Web of Science ®Google Scholar
• Monick, M.M., Carter, A.B., Gudmundsson, G., Mallampalli, R., Powers, L.S. and Hunninghake, G.W. (1999) "A phosphatidylcholine-specific phospholipase C regulates activation of p42/44 mitogen-activated protein kinases in lipopolysaccharide-stimulated human alveolar macrophages", J. Immunol. 162, 3005–3012.
   PubMed Web of Science ®Google Scholar
• Zhou, D., Lauderback, C.M., Yu, T., Brown, S.A., Butterfield, D.A. and Thompson, J.S. (2001) "D609 inhibits ionizing radiation-induced oxidative damage by acting as a potent antioxidant", J. Pharmacol. Exp. Ther. 298, 103–109.
   PubMedGoogle Scholar
• Amtmann, E. (1996) "The antiviral, antitumoural xanthate D609 is a competitive inhibitor of phosphatidylcholine-specific phospholipase C", Drugs Exp. Clin. Res. 22, 287–294.
   PubMedGoogle Scholar
• Rao, S.R. (1971) "Xanthates and related compounds (Marcel Dekker, New York)—specific phospholipase C and acidic sphingomyelinase in the propagation of the apoptotic signal", EMBO J. 14, 5859–5868.
   Google Scholar
• Butterfield, D.A., Yatin, S.M., Varadarajan, S. and Koppal, T. (1999) "Amyloid I3-peptide-associated free radical oxidative stress, neurotmdcity, and Alzhemeir's disease", Methods Enzymol. 309, 746–768.
   PubMed Web of Science ®Google Scholar
• Yatin, S.M., Varadarajan, S. and Butterfield, D.A. (2000) "Vitamin E prevents Alzheimer's amyloid beta-peptide (1-42)-induced neuronal protein oxidation and reactive oxygen species production", J. Alzheimer's Dis. 2, 123–131.
   PubMedGoogle Scholar
• Barany, G., Schroll, A.L., Mott, A.W. and Halsrud, D.A. (1983) "A general strategy for elaboration of the dithiocarbonyl functionality, —(C=0)SS—: application to the synthesis of bis(chlorocarbonyl) disulfane and related derivatives of thiocarbonic acids", J. Org. Chem. 48, 4750–4761.
   Web of Science ®Google Scholar
• Butterfield, D.A. and Stadtman, E.R. (1997) "Protein oxidation processes in aging brain", Adv. Cell Aging Gerontol. 2, 161–191.
   Google Scholar
• Goodman, Y., Bruce, A.J., Cheng, B. and Mattson, M.P. (1996) "Estrogens attenuate and corticosterone exacerbates excito-toxicity, oxidative injury, and amyloid beta-peptide toxicity in hippocampal neurons", J. Neurochem. 66, 1836–1844.
   PubMed Web of Science ®Google Scholar
• Lauderback, C.M., Hackett, J.M., Huang, F.F., Keller, J.N., Szweda, L.I., Markesbery, W.R. and Butterfield, D.A. (2001) "The glial glutamate transporter, GLT-1, is oxidatively modified by 4-hydroxy-2-nonenal in the Alzheimer's disease brain: the role of Abeta1 —42", J. Neurochem. 78, 413–416.
   PubMed Web of Science ®Google Scholar
• Darzynkiewicz, Z., Li, X. and Gong, J. (1994) "Assays of cell viability: discrimination of cells dying by apoptosis", In: Robinson, J.P. and Crissman, H.A., eds, Methods in Cell Biology (Academic Press, New York), pp 15–38.
   Google Scholar
• Bradford, M.M. (1976) "A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein—dye binding", Anal. Biochem. 72, 248–254.
   PubMed Web of Science ®Google Scholar
• Yatin, S.M., Varadarajan, S., Link, C.D. and Butterfield, D.A. (1999) "In vitro and in vivo oxidative stress associated with Alzheimer's amyloidbeta-peptide (1-42)", Neurobiol. Aging 20, 325–330.
   PubMed Web of Science ®Google Scholar
• Mark, R.J., Lovell, MA., Markesbery, W.R., Uchida, K. and Mattson, M.P. (1997) "A role for 4-hydroxynonenal, an aldehydic product of lipid permddation, in disruption of ion homeostasis, and neuronal death induced by amyloid I3-peptide", J. Neurochem. 68, 255–264.
   PubMed Web of Science ®Google Scholar
• Kim, H.C., Yamada, K., Nitta, A., Olariu, A., Tran, M.H., Mizuno, M., Nakajima, A., Nagai, T., Kamei, H., Jhoo, W.K., Im, D.H., Shin, E.J., Hjelle, 0.P., Ottersen, 0.P., Park, S.C., Kato, K., Mirault, M.E. and Nabeshima, T. (2003) "Immuno-cytochemical evidence that amyloid beta (1 – 42) impairs endogenous antioxidant systems in vivo", Neuroscience 119, 399–419.
   PubMed Web of Science ®Google Scholar
• Yu, B.P. (1994) "Cellular defenses against damage from reactive oxygen species", Physiol. Rev. 74, 139–162.
   PubMed Web of Science ®Google Scholar
• Castegna, A., Aksenov, M., Aksenova, M., Thongboonkerd, V, Klein, J.B., Pierce, W.M., Booze, R., Markesbery, W.R. and Butterfield, D.A. (2002) "Proteomic identification of mdda-tively modified proteins in Alzheimer's disease brain. Part I: creatine kinase BB, glutamine synthase, and ubiquitin carboxy-terminal hydrolase L-1", Free Radic. Biol. Med. 33, 562–571.
   PubMed Web of Science ®Google Scholar
• Castegna, A., Aksenov, M., Thongboonkerd, V, Klein, J.B., Pierce, W.M., Booze, R., Markesbery, W.R. and Butterfield, D.A. (2002) "Proteomic identification of mdda-tively modified proteins in Alzheimer's disease brain. Part II: dihydropyrimidinase-related protein 2, alpha-enolase and heat shock cognate 71", J. Neurochem. 82, 1524–1532.
   PubMed Web of Science ®Google Scholar
• Castegna, A., Thongboonkerd, V, Klein, J.B., Lynn, B., Markesbery, W.R. and Butterfield, D.A. (2003) "Proteomic identification of nitrated proteins in Alzheimer's disease brain", J. Neurochem. 85, 1394–1401.
   PubMed Web of Science ®Google Scholar
• Arias, I.M., Jakoby, W.B., eds, (1976) Glutathione: Metabolism and Function (Raven Press, New York).
   Google Scholar
• Hayes, J.D. and McLellan, L.I. (1999) "Glutathione and glutathione-dependent enzymes represent a co-ordinately regulated defense against oxidative stress", Free Radic. Res. 31, 273–300.
   PubMed Web of Science ®Google Scholar
• Dringen, R., Kussmaul, L., Gutterer, J.M., Hirrlinger, J. and Hamprecht, B. (1999) "The glutathione system of peroxidase detoxification is less efficient in neurons than in astroglial cells", J. Neurochem. 72, 2523 —2530.
   Google Scholar
• Butterfield, D.A., Pocernich, C.B. and Drake, J. (2002) "Elevated glutathione as a therapeutic strategy in Alzhei-mer's disease pathology", Drug Dev. Res. 56, 428–437.
   Google Scholar
• Aksenov, MY., Aksenova, MV., Butterfield, D.A., Geddes, J.W. and Markesbery, W.R. (2001) "Protein oxidation in the brain in Alzheimer's disease", Neuroscience 103, 373–383.
   PubMed Web of Science ®Google Scholar
• Omar, R.A., Chyan, Y.J., Andorn, A.C., Poeggeler, B., Robakis, N.K. and Pappolla, M.A. (1999) "Increased expression but reduced activity of antioxidant enzymes in Alzheimer's disease", J. Alzheimer's Dis. 1, 139–145.
   PubMedGoogle Scholar
• Cu, M., Owen, A.D., Toffa, SE., Cooper, J.M., Dexter, D.T., Jenner, P., Marsden, C.D. and Schapira, A.H. (1998) "Mitochondrial function, GSH and iron in neurodegeneration and Lewy body diseases", J. Neurol. Sci. 11, 24–29.
   Google Scholar
• Subramaniam, R., Roediger, F., Jordan, B., Mattson, M.P., Keller, J.N., Waeg, G. and Butterfield, D.A. (1997) "The lipid peroxidation product, 4-hydroxy-2-trans-nonenal, alters the conformation of cortical synaptosomal membrane proteins", J. Neurochem. 69, 1161–1169.
   PubMed Web of Science ®Google Scholar
• Montine, KS., Olson, S.J., Amarnath, V., VVhetsell, Jr., W.O., Graham, D.G. and Montine, T.J. (1997) "Immunohisto-chemical detection of 4-hydroxy-2-nonenal adducts in Alzheimer's disease is associated with inheritance of APOE4", Am. J. Pathol. 150, 437–443.
   PubMedGoogle Scholar
• Sayre, L.M., Zelasko, D.A., Harris, P.L., Perry, G., Salomon, R.G. and Smith, M.A. (1997) "4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease", J. Neurochem. 68, 2092–3007.
   PubMed Web of Science ®Google Scholar
• Markesbery, W.R. and Lovell, M.A. (1998) "Four-hydroxy-nonenal, a product of lipid peroxidation, is increased in the brain in Alzheimer's disease", Neurobiol. Aging 19, 133–136.
   PubMedGoogle Scholar
• Xie, C., Lovell, M.A. and Markesbery, W.R. (1998) "Glutathione transferase protects neuronal cultures against four hydroxynonenal toxicity", Free Radic. Biol. Med. 25, 979–988.
   PubMed Web of Science ®Google Scholar
• Koppal, T., Drake, J., Yatin, S., Jordan, B., Varadarajan, S., Bettenhausen, L. and Butterfield, D.A. (1999) "Peroxynitrite-induced alterations in synaptosomal membrane proteins: insight into oxidative stress in Alzheimer's disease", J. Neurochem. 72, 310–317.
   PubMed Web of Science ®Google Scholar
• Anderson, M.E., Levy, E.J. and Meister, A. (1994) "Preparation and use of glutathione monoesters", Methods Enzymol. 234, 492–499.
   PubMedGoogle Scholar
• Koh, J.Y., Yang, L.L. and Cotman, C.W. (1990) "Beta-amyloid protein increases the vulnerability of cultured cortical neurons to excitotoxic damage", Brain Res. 533, 315–320.
   PubMed Web of Science ®Google Scholar
• Butterfield, D.A., Boyd-Kimball, D. and Castegna, A. (2003) "Proteomics in Alzheimer's disease: insights into potential mechanisms of neurodegeneration", J. Neurochem. 86, 1313–1327.
   PubMed Web of Science ®Google Scholar
• Nitsch, R.M., Blusztajn, J.K., Pittas, A.G., Slack, B.E., Growdon, J.H. and Wurtman, R.J. (1992) "Evidence for a membrane defect in Alzheimer disease brain", Proc. Natl Acad. Sci. USA 89, 1671–1675.
   PubMed Web of Science ®Google Scholar
• Svennerholm, L. and Gottfries, C.G. (1994) "Membrane lipids, selectively diminished in Alzheimer brains, suggest synapse loss as a primary event in early-onset form (type I) and demyelination in late-onset form (type II)", J. Neurochem. 62, 1039–1047.
   PubMed Web of Science ®Google Scholar
• Esterbauer, H., Schaur, R.J. and Zollner, H. (1991) "Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde, and related aldehydes", Free Radic. Biol. Med. 11, 81–128.
   PubMed Web of Science ®Google Scholar
• Subbarao, K.V., Richardson, J.S. and Ang, L.C. (1990) "Autopsy samples of Alzheimer's cortex show increased peroxidation in vitro", J. Neurochem. 55, 342–345.
   PubMed Web of Science ®Google Scholar
• McIntosh, L.J., Trush, M.A. and Troncoso, J.C. (1997) "Increased susceptibility of Alzheimer's disease temporal cortex to oxygen free radical-mediated processes", Free Radic. Biol. Med. 23, 183–190.
   PubMed Web of Science ®Google Scholar
• Nourooz-Zadeh, J., Liu, E.H., Yhlen, B., Anggard, E.E. and Halliwell, B. (1999) "F4-Isoprostanes as specific marker of docosohexaenoic acid peroxidation in Alzheimer's disease", J. Neurochem. 72, 734–740.
   PubMed Web of Science ®Google Scholar
• Lovell, M.A., Ehmann, W.D., Mattson, M.P. and Markesbery, W.R. (1997) "Elevated 4-hydroxynonenal in ventricular fluid in Alzheimer's disease", Neurobiol. Aging 18, 457–461.
   PubMed Web of Science ®Google Scholar
• Ratan, R.R. and Baraban, J.M. (1995) "Apoptotic death in an in vitro model of neuronal oxidative stress", Clin. Exp. Pharmacol. Physiol. 22, 309–310.
   PubMedGoogle Scholar
• Mattson, M.P., Barger, S.W., Cheng, B., Lieberburg, I., Smith-Swintosky, V.L. and Rydel, R.E. (1993) "I3-Amyloid precursor protein metabolites and loss of neuronal Ca2+ homeostasis in Alzheimer's disease", Trends Neurosci. 16, 409–416.
   PubMed Web of Science ®Google Scholar