Skip to main content
SpringerLink
Log in

Influence of Substituents on the Lappaconitine Acetylenic Derivatives Photodegradation

  • Published:
Applied Magnetic Resonance Aims and scope Submit manuscript

Abstract

The natural alkaloid lappaconitine, the anthranilic acid ester, is used against arrhythmias in medical practice, but it undergoes significant photodegradation. The latter may be the cause of the drugs phototoxicity. Furthermore, other esters of anthranilic acid are also widely used in practice, for example, as UV filters; so their photostability is an important characteristic. Thus, the improvement of these compounds resistance against light irradiation is the issue of the day. This work has shown that the appending of a substituent through the acetylene bridge into the anthranilic acid aromatic ring can significantly decrease the lappaconine derivatives photodegradation degree. The photodegradation process, according to the chemically induced dynamic nuclear polarization (CIDNP) analysis, begins with intramolecular or intermolecular reversible electron transfer (ET) with subsequent cleavage of the ester bond. The main product of the photolysis is the quaternary ammonium salt of 20-ethyl-1-α,14-α,16-β-trimethoxyaconitane-4,8,9-triol (lappaconine) of substituted anthranilic acid. It was demonstrated that the photodegradation of the lappaconitine acetylenic derivatives occurs from their triplet excited states and the substitution influences primarily the triplet reactive state formation effectivity.

Graphical Abstract

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 1
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. M.S. Butler, Nat. Prod. Rep. 25, 475 (2008)

    Article  Google Scholar 

  2. S. Neidle, Cancer Drug Design and Discovery, 1st edn. (Elsevier, Amsterdam, 2008)

    Google Scholar 

  3. Xiao-Tian Liang, Wei-Shuo Fang, Medicinal Chemistry of Bioactive Natural Products (Wiley, New York, 2006)

    Book  Google Scholar 

  4. A. Beeby, A.E. Jones, Photochem. Photobiol. 72(1), 10 (2000)

    Article  Google Scholar 

  5. F.N. Dzhakhangirov, M.N. Sultankhodzhaev, B. Tashkhodzhaev, B.T. Salimov, Chem. Nat. Compd. ((Engl. Transl.) 33(2), 190 (1997)

    Article  Google Scholar 

  6. J.F. Heubach, A. Schuele, Planta Med. 64(1), 22 (1998)

    Article  Google Scholar 

  7. S.N. Wright, Mol. Pharmacol. 59, 183 (2001)

    Google Scholar 

  8. N.E. Polyakov, V.K. Khan, M.B. Taraban, T.V. Leshina, O.A. Luzina, N.F. Salakhutdinov, G.A. Tolstikov, Org. Biomol. Chem. 3, 881 (2005)

    Article  Google Scholar 

  9. N.E. Polyakov, T.V. Leshina, Russ. Chem. Bull. Int. Ed. 56, 631 (2007)

    Article  Google Scholar 

  10. N.E. Polyakov, T.V. Leshina, A.V. Tkachev, I.A. Nikitina, N.A. Pankrushina, J. Photochem. Photobiol. A: Chem. 197, 290 (2008)

    Article  Google Scholar 

  11. N.E. Polyakov, O.A. Simaeva, M.B. Taraban, T.V. Leshina, T.A. Konovalova, L.D. Kispert, I.A. Nikitina, N.A. Pankrushina, A.V. Tkachev, J. Phys. Chem. B 114(13), 4646 (2010)

    Article  Google Scholar 

  12. H.H. Tonnesen, The Photostability of Drugs and Drug Formulations (Taylor & Francis, London, 1996)

    Google Scholar 

  13. S.E. Thomas, M.L. Wood, Br. Med. J. 292, 992 (1986)

    Article  Google Scholar 

  14. L. Langseth, Oxidants, Antioxidants and Disease Prevention (International Life Science Institute, Belgium, 1996)

    Google Scholar 

  15. J.V. Castell, M.J. Gomez-Lechon, D. Hernandez, L.A. Martinez, M.A. Miranda, Photochem. Photobiol. 60, 586 (2008)

    Article  Google Scholar 

  16. J.V. Greenhill, M.A. McLelland, Progr. Med. Chem. 27, 51 (1990)

    Article  Google Scholar 

  17. J.V. Greenhill, in The Photostability of Drugs and Drug Formulations, ed. by H.H. Tonnesen, (Taylor & Francis, London, 1996), pp. 83–110

  18. B.D. Glass, M.E. Brown, P.M. Drummond, in Drugs Photochemistry and Photostability, ed. by A. Albini, E. Fasani (Royal Society of Chemistry, Cambridge, UK, 1998), pp. 134–149

  19. N.A. Pankrushina, I.A. Nikitina, N.V. Anferova, S.A. Osadchii, M.M. Shakirov, E.E. Shults, G.A. Tolstikov, Russ. Chem. Bull. Int. Ed. 52, 2490 (2003)

    Article  Google Scholar 

  20. D.A. Filimonov, V.V. Poroikov, Russ. Chem. J. 50, 66 (2006)

    Google Scholar 

  21. A.A. Stepanov, S.F. Vasilevsky, G.A. Tolstikov, Chem. Sustain. Dev. (Article in Russian) 8, 505 (2010)

    Google Scholar 

  22. S.A. Osadchii, E.E. Shul’ts, S.F. Vasilevsky, E.V. Polukhina, A.A. Stepanov, G.A. Tolstikov, Russ. Chem. Bull. Int. 56(2), 356 (2007)

    Article  Google Scholar 

  23. V.S. Kornievskaya, A.I. Kruppa, N.E. Polyakov, T.V. Leshina, J. Phys. Chem. B 111, 11447 (2007)

    Article  Google Scholar 

  24. V.S. Kornievskaya, A.I. Kruppa, T.V. Leshina, J. Incl. Phenom. Macrocycl. Chem. 60, 123 (2008)

    Article  Google Scholar 

  25. H. Shimada, A. Nakamura, T. Yoshihara, S. Tobita, Photochem. Photobiol. Sci. 4, 367 (2005)

    Article  Google Scholar 

  26. D. Decroocq, Bull. Soc. Chim. France 1, 127 (1964)

    Google Scholar 

  27. H Landolt; R Börnstein; R A Forrester; Hanns Fischer; K H Hellwege, Landolt-Börnstein, Numerical Data and Functional Relationships in Science and Technology. Group 2, Atomic and Molecular Physics, vol. 9, Magnetic Properties of Free Radicals. Pt.d2, Organic Cation Radical and Polyradicals. (Springer, Berlin, 1980)

  28. C.L. Talcott, R.J. Myers, Mol. Phys. 12(6), 549 (1967)

    Article  ADS  Google Scholar 

  29. K.M. Salikhov, Y.N. Molin, R.Z. Sagdeev, A.L. Buchachenko, Spin Polarization and Magnetic Field Effects in Radical Reaction (Akademiai Kiado, Budapest, 1984)

    Google Scholar 

  30. M.M. Carrabba, J.E. Kenny, W.R. Moomaw, J. Cordes, M. Denton, J. Phys. Chem. 89, 674 (1985)

    Article  Google Scholar 

  31. N.E. Polyakov, M.B. Taraban, T.V. Leshina, Photochem. Photobiol. 80, 565–571 (2004)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemical Kinetics and Combustion, Novosibirsk, 630090, Russia

    A. A. Schlotgauer, V. I. Klimentiev, V. S. Kornievskaya, N. E. Polyakov, A. A. Stepanov, S. F. Vasilevsky & T. V. Leshina

  2. Novosibirsk State University, Novosibirsk, 630090, Russia

    A. A. Stepanov & S. F. Vasilevsky

Authors
  1. A. A. Schlotgauer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Klimentiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. S. Kornievskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. E. Polyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Stepanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. F. Vasilevsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. T. V. Leshina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Schlotgauer.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Schlotgauer, A.A., Klimentiev, V.I., Kornievskaya, V.S. et al. Influence of Substituents on the Lappaconitine Acetylenic Derivatives Photodegradation. Appl Magn Reson 46, 559–573 (2015). https://doi.org/10.1007/s00723-015-0644-9

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00723-015-0644-9

Keywords

Search

Navigation