Skip to main content
Log in

Spectral–Luminescent and Spectrophotometric Study of Molecular and Anionic Forms of N-Methyl Derivatives of 5-Fluorouracil in Aqueous Solutions

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

Abstract

Spectrophotometric and fluorescent (FL) methods have been used to study solutions of N-methyl derivatives of 5-fluorouracil (FU): 1-methyl-5-fluorouracil (1M-FU), 3-methyl-5-fluorouracil (3M-FU), and 1,3-dimethyl-5-fluorouracil (1,3DM-FU) in neutral (pH 6.8) and alkaline (pH 11) aqueous media. Fluorescence parameters, such as FL spectrum and quantum yield (φ), of 1M-FU, 3M-FU, 1,3DM-FU, and their anionic forms were recorded for the first time. Bathofluoric shifts in the FL maxima and an increase in the FL quantum yields of these compounds compared to unsubstituted FU at pH 6.8 and pH 11 have been observed. Interpretation of the revealed features is presented.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.

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. Nucleic Acids in Chemistry and Biology, Blackburn, G.M. and Gait, M.J., Eds., Oxford: Oxford University Press, 1996, 2nd ed.

    Google Scholar 

  3. Morris, S.M., Mutat. Res., 1993, vol. 297, p. 39.

    Article  CAS  Google Scholar 

  4. Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Novaya Volna, 2002, vol. 2.

  5. Bol’shaya meditsinskaya entsiklopediya (Big Medical Encyclopedia), Petrovskii, B., Ed., Moscow: Sovetskaya Entsiklopediya, 1981, vol. 15, 3rd ed.

    Google Scholar 

  6. Gimadieva, A.R., Myshkin, V.A., Mustafin, A.G., Chernyshenko, Y.N., Borisova, N.S., Zimin, Y.S., and Abdrakhmanov, I.B., Pharm. Chem. J., 2014, vol. 48, p. 93.

    Article  CAS  Google Scholar 

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

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

    CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  10. 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 

  11. Gustavsson, T., Bányász, Á., 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 

  12. Ostakhov, S.S., Sultanbaev, M.V., Ovchinnikov, M.Yu., Kayumova, R.R., and Khursan, S.L., High Energy Chem., 2017, vol. 51, no. 2, p. 108.

    Article  CAS  Google Scholar 

  13. Ostakhov, S.S., Sultanbaev, M.V., Khursan, S.L., Shishlov, N.M., Lebedev, Yu.A., and Kinzyabulatov, R.R., High Energy Chem., 2014, vol. 48, no. 5, p. 330.

    Article  CAS  Google Scholar 

  14. Ostakhov, S.S. and Sultanbaev, M.V., Mendeleev Commun., 2012, vol. 22, no. 1, p. 23.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Sultanbaev, M.V., Ostakhov, S.S., Gantsev, Sh.Kh., Khaliullin, F.A., and Kazakov, V.P., High Energy Chem., 2010, vol. 44, no. 5, p. 383.

    Article  CAS  Google Scholar 

  17. Ostakhov, S.S., Ovchinnikov, M.Y., Masyagutova, G.A., and Khursan, S.L., J. Phys. Chem. A, 2019, vol. 123, no. 37, p. 7956.

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  20. Buranbaeva, R.S., Lobov, A.N., Grabovskii, S.P., and Ivanov, S.P., Vestn. Bashkir. Univ., 2017, vol. 22, no. 1, p. 48.

    Google Scholar 

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

    Article  Google Scholar 

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

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

Download references

ACKNOWLEDGMENTS

Spectral-luminescence measurements were performed using the equipment of the “Khimiya” Shared-Use Center at the Ufa Institute of Chemistry of the Ural Federal Research Center and the “Agidel” Republican Shared- Use Center at the Ural Federal Research Center of the Russian Academy of Sciences.

Funding

The work was carried out within the framework of the State Assignment on the topics of research at the Ural Institute of Chemistry of the Ural Federal Research Center of the Russian Academy of Sciences: “Mechanism and kinetic patterns of oxidative transformations involving highly active intermediates in chemical and biochemical processes” and “Establishment of the structure, composition and physicochemical properties of organic, bioorganic, polymeric molecules and coordination compounds by methods of chromatography, mass spectrometry, IR, UV, EPR and NMR spectroscopy.”

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. S. Ostakhov.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated by S. Zatonsky

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ostakhov, S.S., Abdrakhimova, G.S., Kayumova, R.R. et al. Spectral–Luminescent and Spectrophotometric Study of Molecular and Anionic Forms of N-Methyl Derivatives of 5-Fluorouracil in Aqueous Solutions. High Energy Chem 56, 158–162 (2022). https://doi.org/10.1134/S0018143922030080

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0018143922030080

Keywords:

Navigation