Skip to main content

Advertisement

SpringerLink
Log in

Copper catalysed oxidation of amino acids and Alzheimer's disease

  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

Abstract

Metal-catalyzed oxidation (MCO) can lead to damage of bio-molecules and is implicated in neurodegenerative diseases, such as Alzheimer's disease (AD). The amino acid residues, tyrosine, histidine and methionine, have been proposed to play important roles in metal mediated oxidative stress and subsequent reactions of amyloid β peptide (Aβ) a major contributor in the pathogenesis of AD. The MCO of Aβ residues, particularly histidine, methionine and tyrosine, are reviewed. MCO of Aβ histidine and tyrosine residues can facilitate oligomerization and may play a role in both amyloid formation and Aβ neurotoxicity. Further work is needed to determine the importance of Aβ oxidation in AD and the role of Aβ oxidation products and oxidative stress in disease progression. The mechanisms of Aβ MCO are complex and multiple reaction products can form. Further study is needed to determine the mechanisms by which Aβ MCO occurs in vivo. In addition, new analytical methods are required to monitor the formation of Aβ MCO products formed during AD. The copper–H2O2 redox system provides a chemical model by which Aβ MCO can be studied in vitro and can be used to produce oxidatively modified amino acid residues for use as standards in developing new analytical methods to monitor Aβ MCO.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Bush, A.I., Curr. Opin. Chem. Biol., 4 (2000) 184.

    CAS  PubMed  Google Scholar 

  2. Varadarajan, S., Yatin, S., Aksenova, M. and Butterfield, D. A., J. Struct. Biol., 130 (2000) 184.

    Article  CAS  PubMed  Google Scholar 

  3. Beyreuther, K., Christen, Y. and Masters, C.L., Neurodegenerative Disorders: Loss of Function Through Gain of Function, Springer-Verlag, 2001, 97–117.

  4. Stadtman, E.R. and Berlett, B.S., Chem. Res. Toxicol., 10 (1997) 485.

    Article  CAS  PubMed  Google Scholar 

  5. Berlett, B.S. and Stadtman, E.R., J. Biol. Chem., 272 (1997) 20313.

    Article  CAS  PubMed  Google Scholar 

  6. Christen, Y., Am. J. Clin. Nutr., 71 (2000) 621S.

    CAS  PubMed  Google Scholar 

  7. Vatassery, G.T., Bauer, T. and Dysken, M., Am. J. Clin. Nutr., 70 (1999) 793.

    CAS  PubMed  Google Scholar 

  8. Curtain, C., Ali, F., Volitakis, I., Cherny, R., Norton, R., Beyreuther, K., Barrow, C., Masters, C., Bush, A. and Barnham, K., J. Biol. Chem., 276 (2001) 20466.

    Article  CAS  PubMed  Google Scholar 

  9. Ali, F., Thompson, A.J. and Barrow, C.J., Aust. J. Chem., 53 (2000) 321.

    Article  CAS  Google Scholar 

  10. Curtain, C.C., Ali, F.E., Smith, D.G., Bush, A.I., Masters, C.L. and Barnham, K.J., J. Biol. Chem., 278 (2003) 2977.

    Article  CAS  PubMed  Google Scholar 

  11. Barnham, K.J., Ciccotosto, G.D., Tickler, A.K., Ali, F.E., Smith, D.G., Williamson, N.A., Lam, Y.-H., Carrington, D., Tew, D., Kocak, G., Volitakis, I., Separovic, F., Barrow, C.J., Wade, J.D., Masters, C.L., Cherny, R.A., Curtain, C.C., Bush, A.I. and Cappai, R., J. Biol. Chem., 278 (2003) 42959.

    CAS  PubMed  Google Scholar 

  12. Ali, F.E.A., Metal catalyzed oxidative damage and conformational changes of amyloid-peptide (Abeta) in Alzheimer's disease, University of Melbourne, Parkville, 2002.

    Google Scholar 

  13. Huang, X., Cuajungco, M.P., Atwood, C.S., Hartshorn, M.A., Tyndall, J.D.A., Hanson, G.R., Stokes, K.C., Leopold, M., Multhaup, G., Goldstein, L.E., Scarpa, R.C., Saunders, A.J., Lim, J., Moir, R.D., Glahe, C., Bowden, E.F., Masters, C.L., Fairlie, D.P., Tanzi, R.E. and Bush, A.I., J. Biol. Chem., 274 (1999) 37111.

    CAS  PubMed  Google Scholar 

  14. Chevion, M., Berenshtein, E. and Stadtman, E.R., Free Radic. Res., 33 (2000) S99.

    CAS  PubMed  Google Scholar 

  15. Bondy, S.C., Guo-Ross, S.X. and Truong, A.T. Brain Res., 799 (1998) 91.

    Article  CAS  PubMed  Google Scholar 

  16. Behl, C., Davis, J.B., Lesley, R. and Schubert, D., Cell, 77 (1994) 817.

    Article  CAS  PubMed  Google Scholar 

  17. Brzyska, M., Bacia, A. and Elbaum, D., Eur. J. Biochem., 268 (2001) 3443.

    Article  CAS  PubMed  Google Scholar 

  18. Lynch, T., Cherny, R.A. and Bush, A.I., Exp. Gerontol., 35 (2000) 445.

    Article  CAS  PubMed  Google Scholar 

  19. Huang, X., Atwood, C.S., Hartshorn, M.A., Multhaup, G., Goldstein, L.E., Scarpa, R.C., Cuajungco, M.P., Gray, D.N., Lim, J., Moir, R.D., Tanzi, R.E. and Bush, A.I., Biochem., 38 (1999) 7609.

    CAS  Google Scholar 

  20. Atwood, C.S., Moir, R.D., Huang, X.D., Scarpa, R.C., Bacarra, N.M.E., Romano, D.M., Hartshorn, M.K., Tanzi, R.E. and Bush, A.I., J. Biol. Chem., 273 (1998) 12817.

    Article  CAS  PubMed  Google Scholar 

  21. Giunta, S., Ronchi, P., Valli, B., Franceschi, C. and Galeazzi, L., Amyloid, 7 (2000) 189.

    CAS  PubMed  Google Scholar 

  22. Dyrks, T., Dyrks, E., Masters, C.L. and Beyreuther, K., FEBS Lett., 324 (1993) 231.

    Article  CAS  PubMed  Google Scholar 

  23. Yang, C., Chem. J. Internet., 2 (2000) 35.

    Google Scholar 

  24. Atwood, C.S., Huang, X., Khatri, A., Scarpa, R.C., Kim, Y.-S., Moir, R.D., Tanzi, R.E., Roher, A.E. and Bush, A.I., Cell Mol. Biol., 46 (2000) 777.

    CAS  PubMed  Google Scholar 

  25. Holley, A. and Cheeseman, K., Br. Med. Bull., 49 (1993) 494.

    CAS  PubMed  Google Scholar 

  26. Kang, J.O., Chan, P.C. and Kesner, L., Inorg. Chim. Acta., 107 (1985) 253.

    CAS  Google Scholar 

  27. Amici, A., Levine, R.L., Tsai, L. and Stadtman, E.R., J. Biol. Chem., 264 (1989) 3341.

    CAS  PubMed  Google Scholar 

  28. Griffiths, H.R., Free Radic. Res., 33 (2000) S47.

    CAS  PubMed  Google Scholar 

  29. Fu, S.L., Fu, M.X., Baynes, J.W., Thorpe, S.R. and Dean, R.T., Biochem. J., 330 (1998) 233.

    CAS  PubMed  Google Scholar 

  30. Arai, H., Kashiwagi, S., Nagasaka, Y., Uchida, K., Hoshii, Y. and Nakamura, K., Arch. Biochem. Biophys., 367 (1999) 1.

    Article  CAS  PubMed  Google Scholar 

  31. Leeuwenburgh, C., Hansen, P.A., Holloszy, J.O. and Heinecke, J.W., Am. J. Physiol., 45 (1999) R128.

    Google Scholar 

  32. Giulivi, C. and Davies, K.J.A., J. Biol. Chem., 276 (2001) 24129.

    Article  CAS  PubMed  Google Scholar 

  33. Sychev, A.Y., Izv. Vyssh. Ucheb. Zaved., Khim. Khim. Tekhnol., 12 (1969) 1666.

    CAS  Google Scholar 

  34. Bakurdzhieva, N., Dokl. Bolg. Akad. Nauk., 23 (1970) 591.

    CAS  Google Scholar 

  35. Fu, S., Gebicki, S., Jessup, W., Gebicki, J. and Dean, R., Biochem. J., 311 (1995) 821.

    CAS  PubMed  Google Scholar 

  36. Stadtman, E.R. and Berlett, B.S., J. Biol. Chem., 266 (1991) 17201.

    CAS  PubMed  Google Scholar 

  37. Luxford, C., Dean, R.T. and Davies, M.J., Biogerontology, 3 (2002) 95.

    Article  CAS  PubMed  Google Scholar 

  38. Fu, S.L. and Dean, R.T., Biochem. J., 324 (1997) 41.

    CAS  PubMed  Google Scholar 

  39. Balakrishnan, R., Parthasarathy, R. and Sulkowski, E., J. Pept. Res., 51 (1998) 91.

    CAS  PubMed  Google Scholar 

  40. Schubert, J. and Wilmer, J.W., Free Radic. Biol. Med., 11 (1991) 545.

    Article  CAS  PubMed  Google Scholar 

  41. Sestili, P., Cantoni, O., Cattabeni, F. and Murray, D., Biochim. Biophys. Acta., 1268 (1995) 130.

    PubMed  Google Scholar 

  42. Cantoni, O. and Giacomoni, P., Gen. Pharmacol., 29 (1997) 513.

    Article  CAS  PubMed  Google Scholar 

  43. Tachon, P., Deflandre, A. and Giacomoni, P.U., Carcinogenesis, 15 (1994) 1621.

    CAS  PubMed  Google Scholar 

  44. Steffek, R.P. and Thomas, M.J., Free Radic. Res. Commun., 12–13 (1991) 489.

    PubMed  Google Scholar 

  45. Mahadev, N.L. and Lumpkin, J.A., Proceedings, 211th ACS National Meeting, New Orleans, LA, March 24–28, (1996) BIOT-072.

  46. Sharma, V.S., Schubert, J., Brooks, H.B. and Sicilio, F., J. Am. Chem. Soc., 92 (1970) 822.

    Article  CAS  Google Scholar 

  47. Nair, C.P.P. and Stokstad, E.L.R., Indian J. Biochem. Biophys., 29 (1992) 415.

    CAS  PubMed  Google Scholar 

  48. Au, V. and Madison, S.A., Arch. Biochem. Biophys., 384 (2000) 133.

    Article  CAS  PubMed  Google Scholar 

  49. Zhao, F., Ghezzo-Schoneich, E., Aced, G.I., Hong, J., Milby, T. and Schoneich, C., J. Biol. Chem., 272 (1997) 9019.

    CAS  PubMed  Google Scholar 

  50. Li, S., Nguyen, T.H., Schoneich, C. and Borchardt, R.T., Biochemistry., 34 (1995) 5762.

    CAS  PubMed  Google Scholar 

  51. Stadtman, E.R., Free Radic. Biol. Med., 9 (1990) 315.

    CAS  PubMed  Google Scholar 

  52. Varadarajan, S., Yatin, S. and Butterfield, D., Alzheimer's Rep., 3 (2000) 71.

    Google Scholar 

  53. Christensen, B.W. and Kjaer, A., Chem. Commun., (1965) 225.

  54. Marastoni, M., Salvadori, S., Balboni, G., Borea, P.A., Marzola, G. and Tomatis, R., J. Med. Chem., 30 (1987) 1538.

    Article  CAS  PubMed  Google Scholar 

  55. Boonvisut, S., Aksnes, A. and Njaa, L.R., Food Chem., 9 (1982) 183.

    Article  CAS  Google Scholar 

  56. Cuq, J.L., Sci. Aliments, 12 (1992) 315.

    CAS  Google Scholar 

  57. McKee, M.L., J. Am. Chem. Soc., 120 (1998) 3963.

    Article  CAS  Google Scholar 

  58. Jensen, F., Greer, A. and Clennan, E.L., J. Am. Chem. Soc., 120 (1998) 4439.

    CAS  Google Scholar 

  59. Angyan, J.G., Bonnelle, C., Daudel, R., Kucsman, A. and Csizmadia, I.G., Theochemistry, 42 (1988) 273.

    CAS  Google Scholar 

  60. Chao, C.C., Ma, Y.S. and Stadtman, E.R., Proc. Natl Acad. Sci. USA, 94 (1997) 2969.

    Article  CAS  PubMed  Google Scholar 

  61. Such, L., O'Connor, J.-E., Saez, G.T., Gil, F., Beltran, J.F., Moya, A. and Alberola, A., Cytometry, 37 (1999) 140.

    Article  CAS  PubMed  Google Scholar 

  62. Roher, A.E. and Kuo, Y.M., Isolation of Amyloid Deposits from Brain, Academic Press Inc, San Diego, CA, USA, 2000.

    Google Scholar 

  63. Bitan, G., Tarus, B., Vollers, S.S., Lashuel, H.A., Condron, M.M., Straub, J.E. and Teplow, D.B., J. Am. Chem. Soc., 125 (2003) 15359.

    Article  CAS  PubMed  Google Scholar 

  64. Riek, R., Guntert, P., Dobeli, H., Wipf, B. and Wuthrich, K., Eur. J. Biochem., 268 (2001) 5930.

    Article  CAS  PubMed  Google Scholar 

  65. Watson, A.A., Fairlie, D.P. and Craik, D.J., Biochem., 37 (1998) 12700.

    CAS  Google Scholar 

  66. Halcrow, M.A., Angew. Chem., Intl. Ed., 40 (2001) 346.

    Article  CAS  Google Scholar 

  67. Ali, F.E., Barnham, K.J., Barrow, C.J. and Separovic, F., J. Inorg. Biochem., 98 (2004) 173.

    Article  CAS  PubMed  Google Scholar 

  68. Shamovsky, I.L., Riopelle, R.J. and Ross, G.M., J. Phys. Chem. A., 105 (2001) 1061.

    Article  CAS  Google Scholar 

  69. Fu, S., Davies, M.J., Stocker, R. and Dean, R.T., Biochem. J., 333 (1998) 519.

    CAS  PubMed  Google Scholar 

  70. Huggins, T.G., Wells-Knecht, M.C., Detorie, N.A., Baynes, J.W. and Thorpe, S.R., J. Biol. Chem., 268 (1993) 12341.

    CAS  PubMed  Google Scholar 

  71. Mahmoud, S.F. and Bialkowski, S.E., App. Spectrosc., 49 (1995) 1677.

    CAS  Google Scholar 

  72. Gieseg, S.P., Simpson, J.A., Charlton, T.S., Duncan, M.W. and Dean, R.T. Biochemistry, 32 (1993) 4780.

    Article  CAS  PubMed  Google Scholar 

  73. Kato, Y., Kitamoto, N., Kawai, Y. and Osawa, T., Free Radic. Biol. Med., 31 (2001) 624.

    Article  CAS  PubMed  Google Scholar 

  74. Jain, R., Freund, H.G., Budzinsky, E. and Sharma, M., Bioconjug. Chem., 8 (1997) 173.

    Article  CAS  PubMed  Google Scholar 

  75. Haavik, J., J. Neurochem., 69 (1997) 1720.

    CAS  PubMed  Google Scholar 

  76. Galeazzi, L., Ronchi, P., Franceschi, C. and Giunta, S., Amyloid, 6 (1999) 7.

    CAS  PubMed  Google Scholar 

  77. Cherny, R.A., Barnham, K.J., Lynch,T., Volitakis, I., Li, Q.-X., McLean, C.A., Multhaup, G., Beyreuther, K., Tanzi, R.E., Masters, C.L. and Bush, A.I., J. Struct. Biol., 130 (2000) 209.

    Article  CAS  PubMed  Google Scholar 

  78. Tohgi, H., Abe, T., Yamazaki, K., Murata, T., Isobe, C. and Ishizaki, E., J. Neural Transm., 105 (1998) 1283.

    Article  CAS  PubMed  Google Scholar 

  79. Adlard, P.A., West, A.K. and Vickers, J.C., Neurobiol. Dis., 5 (1998) 349.

    Article  CAS  PubMed  Google Scholar 

  80. Hensley, K., Maidt, M.L., Yu, Z., Sang, H., Markesbery, W.R. and Floyd, R.A., J. Neurol. Sci., 18 (1998) 8126.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry, University of Melbourne, VIC, 3010, Australia

    Feda E. Ali, Colin J. Barrow & Frances Separovic

  2. Department of Pathology, University of Melbourne, VIC, 3010, Australia

    Kevin J. Barnham

Authors
  1. Feda E. Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kevin J. Barnham
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Colin J. Barrow
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Frances Separovic
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ali, F.E., Barnham, K.J., Barrow, C.J. et al. Copper catalysed oxidation of amino acids and Alzheimer's disease. Int J Pept Res Ther 10, 405–412 (2003). https://doi.org/10.1007/s10989-004-2391-x

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10989-004-2391-x

Search

Navigation