Skip to main content
SpringerLink
Log in

Spectral-luminescence and quantum-chemical study of the anionic forms of 5-fluorouracil

  • Photonics
  • Published:
High Energy Chemistry Aims and scope Submit manuscript

Abstract

A spectral-luminescence study of neutral (pH 7) and alkaline (pH 11 and 14) aqueous solutions of the anticancer drugs 5-fluorouracil (FU) and tegafur has been performed. The fluorescence spectra of the N3- and N1-centered anions of 5-fluorouracil, its dianion, and the tegafur monoanion with emission maxima at wavelengths (λem) of 358, 372, 366, and 358 nm and photoluminescence quantum yields (φ) of 11.2 × 10–4, 35.1 × 10–4, 26.5 × 10–4, and 8.6 × 10–4, respectively, have been recorded for the first time. The fluorescence characteristics of the FU anionic forms have been related to the magnetic shielding constant as one of the criteria of aromaticity.

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. Watson, J.D. and Crick, F.H.C., Nature, 1953, vol. 171, no. 4361, p. 964.

    Article  CAS  Google Scholar 

  2. Sowers, L.C., Shaw, B.R., Veigl, M.L., and Sedwick, W.D., Mutat. Res., 1987, vol. 177, no. h. 1987, p. 201.

    Article  CAS  Google Scholar 

  3. Berens, K. and Shugar, D., Acta Biochim. Pol., 1963, vol. 10, no. 1, p. 25.

    CAS  Google Scholar 

  4. Wempen, I. and Fox, J.J., J. Am. Chem. Soc., 1964, vol. 86, no. 12, p. 2474.

    Article  CAS  Google Scholar 

  5. Wierzchowski, K.L., Litonska, E., and Shugar, D., J. Am. Chem. Soc., 1965, vol. 87, no. 20, p. p. 4621.

    Article  CAS  Google Scholar 

  6. Suwaiyan, A., Morsy, M.A., and Odah, K.A., Chem. Phys. Lett., 1995, vol. 237, p. 349.

    Article  CAS  Google Scholar 

  7. Morsy, M.A., Al-Somali, A.M., and Suwaiyan, A., J. Phys. Chem. B, 1999, vol. 103, no. 50, p. 11205.

    Article  CAS  Google Scholar 

  8. Parker, C.A., Photoluminescence of Solutions with Applications to Photochemistry and Analytical Chemistry, Amsterdam Elsevier, 1968.

    Google Scholar 

  9. Tatischeff, I. and Klein, R., Photochem. Photobiol., 1975, vol. 22, no. 6, p. 221.

    Article  CAS  Google Scholar 

  10. Frisch, M.J., Trucks, G.W., Schlegel, H.B., et al., Gaussian 09, 2010. http://www.gaussian.com. Cited June 2, 2016.

  11. Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, no. 18, p. 3865.

    Article  CAS  Google Scholar 

  12. Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1997, vol. 78, no. 7, p. 1396.

    Article  CAS  Google Scholar 

  13. Wachters, A.J.H., J. Chem. Phys., 1970, vol. 52, no. 3, p. 1033.

    Article  CAS  Google Scholar 

  14. Tomasi, J., Mennucci, B., and Cammi, R., Chem. Rev., 2005, vol. 105, no. 8, p. 2999.

    Article  CAS  Google Scholar 

  15. Abdrakhimova, G.S., Ovchinnikov, M.Yu., Lobov, A.N., Spirikhin, L.V., Ivanov, S.P., and Khursan, S.L., J. Phys. Org. Chem., 2014, vol. 27, p. 876.

    Article  CAS  Google Scholar 

  16. Bauernschmitt, R. and Ahlrichs, R., Chem. Phys. Lett., 1996, vol. 256, no. 4, p. 454.

    Article  CAS  Google Scholar 

  17. Keith, T.A. and Bader, R.F.W., Chem. Phys. Lett., 1992, vol. 194, no. 1, p. 1.

    Article  CAS  Google Scholar 

  18. Jimenez-Halla, J.O.C., Matito, E., Robles, J., and Sola, M., J. Organomet. Chem., 2006, vol. 691, no. 21, p. 4359.

    Article  CAS  Google Scholar 

  19. Stanger, A., J. Org. Chem., 2005, vol. 71, no. 3, p. 883.

    Article  Google Scholar 

  20. Krasovitskii, B.M. and Bolotin, B.M., Organicheskie lyuminofory (Organic Luminophores,), Moscow Khimiya, 1984.

    Google Scholar 

  21. Schleyer, P.R. and Jiao, H., Pure Appl. Chem., 1996, vol. 68, no. 2, p. 209.

    CAS  Google Scholar 

  22. Gustavsson, T., Banyasz, A., Lazzarotto, E., Markovitsi, D., Scalmani, G., Frisch, M.J., Barone, V., and Improta, R., J. Am. Chem. Soc., 2006, vol. 128, no. 2, p. 607.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa, Bashkortostan, 450054, Russia

    S. S. Ostakhov, M. V. Sultanbaev, M. Yu. Ovchinnikov, R. R. Kayumov & S. L. Khursan

Authors
  1. S. S. Ostakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Sultanbaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Yu. Ovchinnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. R. Kayumov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. L. Khursan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. S. Ostakhov.

Additional information

Original Russian Text © S.S. Ostakhov, M.V. Sultanbaev, M.Yu. Ovchinnikov, R.R. Kayumov, S.L. Khursan, 2017, published in Khimiya Vysokikh Energii, 2017, Vol. 51, No. 2, pp. 116–120.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ostakhov, S.S., Sultanbaev, M.V., Ovchinnikov, M.Y. et al. Spectral-luminescence and quantum-chemical study of the anionic forms of 5-fluorouracil. High Energy Chem 51, 108–112 (2017). https://doi.org/10.1134/S0018143917010076

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0018143917010076

Keywords

Search

Navigation