Skip to main content
SpringerLink
Log in

Kinetics and mechanism of reactions of photoexcited kynurenine with molecules of some natural compounds

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Photochemical reactions involving kynurenines, viz., molecules present in the eye lens, can result in modifications of the lens proteins and cause a development of a cataract. The rate constants of the reactions of photoexcited kynurenine with several amino acids and antioxidants contained in the lens were measured. The most efficient quenchers of triplet kynurenine are amino acids tryptophan and tyrosine, as well as antioxidant ascorbate. In all cases, the quenching reaction proceeds by the electron transfer mechanism, except for the reaction with oxygen where transfer of the triplet energy to the oxygen molecule occurs.

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. A. R. Wegener, Doc. Ophthalmol., 1994, 88, 221.

    Article  Google Scholar 

  2. R. van Heyningen, Nature, 1971, 230, 393.

    Article  Google Scholar 

  3. A. M. Wood and R. J. W. Truscott, Exp. Eye Res., 1993, 56, 317.

    Article  CAS  Google Scholar 

  4. A. M. Wood and R. J. W. Truscott, Vis. Res., 1994, 34, 1369.

    Article  CAS  Google Scholar 

  5. L. M. Bova, A. M. Wood, J. F. Jamie, and R. J. W. Truscott, Invest. Ophthalmol. Vis. Sci., 1999, 40, 3237.

    CAS  Google Scholar 

  6. L. M. Bova, M. H. J. Sweeney, J. F. Jamie, and R. J. W. Truscott, Invest. Ophthalmol. Vis. Sci., 2001, 42, 200.

    CAS  Google Scholar 

  7. L. M. Taylor, J. A. Aquilina, R. H. Willis, J. F. Jamie, and R. J. W. Truscott, FEBS Lett., 2001, 509, 6.

    Article  CAS  Google Scholar 

  8. J. Dillon and S. J. Atherton, Photochem. Photobiol., 1990, 51, 465.

    CAS  Google Scholar 

  9. J. Dillon, R.-H. Wang, and S. J. Atherton, Photochem. Photobiol., 1990, 52, 849.

    CAS  Google Scholar 

  10. R. J. W. Truscott, A. M. Wood, J. A. Carver, M. M. Sheil, G. M. Stutchbury, J. Zhu, and G. W. Kilby, FEBS Lett., 1994, 384, 173.

    Article  Google Scholar 

  11. S. Lerman and R. Borkman, Ophthal. Res., 1976, 8, 335.

    Google Scholar 

  12. R. J. W. Truscott, Int. J. Biochem. Cell Biol., 2003, 35, 1500.WW

    Article  CAS  Google Scholar 

  13. R. J. W. Truscott, Exp. Eye Res., 2005, 80, 709.

    Article  CAS  Google Scholar 

  14. J. Dillon, Lens Res., 1983, 1, 133.

    CAS  Google Scholar 

  15. J. Dillon, Curr. Eye Res., 1984, 3, 145.

    CAS  Google Scholar 

  16. A. Tomoda, Y. Yoneyama, T. Yamaguchi, E. Shirao, and K. Kawasaki, Ophthal. Res., 1990, 22, 152.

    Article  CAS  Google Scholar 

  17. A. R. Ellozy, R. H. Wang, and J. Dillon, Photochem. Photobiol., 1994, 59, 474.

    CAS  Google Scholar 

  18. A. R. Ellozy, R. H. Wang, and J. Dillon, Photochem. Photobiol., 1994, 59, 479.

    CAS  Google Scholar 

  19. C. M. Krishna, S. Uppuluri, P. Riesz, J. S. Zigler, Jr., and D. Balasubramanian, Photochem. Photobiol., 1991, 54, 51.

    CAS  Google Scholar 

  20. K. J. Reszka, P. Bilski, C. F. Chignell, and J. Dillon, Free Rad. Biol. Med., 1996, 20, 23.

    Article  CAS  Google Scholar 

  21. Yu. P. Tsentalovich, O. A. Snytnikova, P. S. Sherin, and M. D. E. Forbes, J. Phys. Chem. A, 2005, 109, 3565.

    Article  CAS  Google Scholar 

  22. O. A. Snytnikova, P. S. Sherin, Yu. P. Tsentalovich, J. Photochem. Photobiol. A: Chem., 2007, 186, 364.

    Article  CAS  Google Scholar 

  23. I. F. Molokov, Yu. P. Tsentalovich, A. V. Yurkovskaya, and R. Z. Sagdeev, J. Photochem. Photobiol. A: Chem., 1997, 110, 159.

    Article  CAS  Google Scholar 

  24. Yu. P. Tsentalovich, L. V. Kulik, N. P. Gritsan, and A. V. Yurkovskaya, J. Phys. Chem. A, 1998, 102, 7975.

    Article  CAS  Google Scholar 

  25. R. V. Bensasson and E. J. Land, Trans. Faraday Soc., 1971, 67, 1904.

    Article  CAS  Google Scholar 

  26. B. Amand and R. V. Bensasson, Chem. Phys. Lett., 1975, 34, 44.

    Article  CAS  Google Scholar 

  27. G. V. Buxton, C. L. Greenstock, W. P. Helman, and A. B. Ross, J. Phys. Chem. Ref. Data, 1988, 17, 513.

    CAS  Google Scholar 

  28. B. H. J. Bielski, D. A. Comstock, and R. A. Bowen, J. Am. Chem. Soc., 1971, 3, 5624.

    Article  Google Scholar 

  29. M. Tamba, A. Torreggiani, and O. Tubertini, Radiat. Phys. Chem., 1995, 46, 569.

    Article  CAS  Google Scholar 

  30. D. Ross, K. Norbeck, and P. Moldeus, J. Biol. Chem., 1985, 260, 15028.

    Google Scholar 

  31. M. Quintiliani, R. Badiello, M. Tamba, and G. Gorin, in Modification of Radiosensitivity of Biological Systems, IAEA, Vienna, 1976, p. 29.

    Google Scholar 

  32. B. Halliwell and J. M. C. Gutteridge, in Free Radicals in Biology and Medicine, 3rd ed., Oxford University Press, New York, 1993, p. 140.

    Google Scholar 

  33. M. Z. Hoffman and E. Hayon, J. Phys. Chem., 1973, 77, 990.

    Article  CAS  Google Scholar 

  34. M. Quintiliani, R. Badiello, M. Tamba, A. Esfandi, and G. Gorin, Int. J. Radiat. Biol., 1977, 32, 195.

    Article  CAS  Google Scholar 

  35. Yu. P. Tsentalovich, O. A. Snytnikova, and R. Z. Sagdeev, J. Photochem. Photobiol. A: Chem., 2004, 162, 371.

    Article  CAS  Google Scholar 

  36. D. V. Bent and E. Hayon, J. Am. Chem. Soc., 1975, 97, 2612.

    Article  CAS  Google Scholar 

  37. F. D. Bryant, R. Santus, and L. I. Grossweiner, J. Phys. Chem., 1975, 79, 2711.

    Article  CAS  Google Scholar 

  38. W. A. Volkert, R. R. Kuntz, C. A. Ghiron, and R. F. Evans, Photochem. Photobiol., 1977, 26, 3.

    CAS  Google Scholar 

  39. J. F. Baugher and L. I. Grossweiner, J. Phys. Chem., 1977, 81, 1349.

    Article  CAS  Google Scholar 

  40. M. L. Posener, G. E. Adams, P. Wardman, and R. B. Cundall, J. Chem. Soc. Faraday Trans. 2, 1976, 72, 2231.

    Article  CAS  Google Scholar 

  41. K. M. Bansal and R.W. Fessenden, Radiat. Res., 1976, 67, 1.

    Article  CAS  Google Scholar 

  42. H. Heath, Exp. Eye Res., 1962, 1, 362.

    Article  CAS  Google Scholar 

  43. M. R. Fernando, M. Satake, V. M. Monnier, and M. F. Lou, Invest. Ophthalmol. Vis. Sci., 2004, 45, 230.

    Article  Google Scholar 

  44. K.-J. Yeum, A. Taylor, G. Tang, and R. M. Russel, Invest. Ophthalmol. Vis. Sci., 1995, 36, 2756.

    CAS  Google Scholar 

  45. R. McNulty, H. Wang, R. T. Mathias, B. J. Ortwerth, R. J. W. Truscott, and S. Bassnett, J. Physiol., 2004, 559, 883.

    CAS  Google Scholar 

  46. L. M. Taylor, J. A. Aquilina, J. F. Jamie, and R. J. W. Truscott, Exp. Eye Res., 2002, 75, 165.

    Article  CAS  Google Scholar 

  47. Yu. P. Tsentalovich, O. A. Snytnikova, M. D. E. Forbes, E. I. Chernyak, and S. V. Morozov, Exp. Eye Res., 2006, 83, 1439.

    Article  CAS  Google Scholar 

  48. L. M. Taylor, J. A. Aquilina, J. F. Jamie, and R. J. W. Truscott, Exp. Eye Res., 2002, 74, 503.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. International Tomography Center, Siberian Branch of the Russian Academy of Sciences, 3a Institutskaya ul., 630090, Novosibirsk, Russian Federation

    O. A. Snytnikova, P. S. Sherin & L. V. Kopylova

  2. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    O. A. Snytnikova, L. V. Kopylova & Yu. P. Tsentalovich

Authors
  1. O. A. Snytnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. S. Sherin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. V. Kopylova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu. P. Tsentalovich
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. A. Snytnikova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 704–710, April, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Snytnikova, O.A., Sherin, P.S., Kopylova, L.V. et al. Kinetics and mechanism of reactions of photoexcited kynurenine with molecules of some natural compounds. Russ Chem Bull 56, 732–738 (2007). https://doi.org/10.1007/s11172-007-0109-x

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0109-x

Key words

Search

Navigation