Abstract
Lappaconitine (LC) is a natural diterpenoid alkaloid (DTA), acting as a human heart sodium channel blocker and possessing a wide range of biological activities, the cellular and molecular mechanisms of which are widely studied. This interest is due to the fact that various representatives of this DTA class show opposite biological activities. The possible reasons for this difference seem to be related to the peculiarities of the substituent effect on the drug-receptor binding process. In this work, the influence of substituents on the reactivity of LC and its derivatives has been studied by using elementary processes of photodecomposition. The given approach includes the joint analysis of the photophysical properties of the studied systems and their photodecomposition quantum yields. It allows us to trace the influence of substituents, located in the diterpenoid skeleton and anthranilic fragment, on processes in both moieties of LC. Summarizing the data obtained, an inverse dependence of fluorescence and photodegradation quantum yields has been observed. This correlation established for LCs, in particular, allows one to propose a way to evaluate the photostability of potential drugs based on fluorescence analysis. This would be appropriate for compounds in which the reactivity depends on intersystem crossing, i.e. in the cases where the initial and reacting excited states differ in multiplicity.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
J. F. Heubach and A. Schüle, Planta Med., 1998, 64, 22–26.
Y. Z. Wang, Y. Q. Xiao, C. Zhang and X. M. Sun, J. Tradit. Clin. Med., 2009, 29, 141–145.
F. Shaheen, M. Ahmad, M. T. H. Khan, S. Jalil, A. Ejaz, M. N. Sultankhodjaev, M. Arfan, M. I. Choudhary and Atta-ur-Rahman, Phytochemistry, 2005, 66, 935–940.
G. I. Solyanik, A. G. Fedorchuk, O. N. Pyaskovskaya, O. I. Dasyukecitch, N. N. Khranovskaya, G. N. Aksenov and V. V. Sobetsky, Exp. Oncol., 2004, 26, 307–311.
A. Ameri, Brain Res., 1997, 767, 36–43.
A. Ameri and T. Simmet, Brain Res., 1999, 842, 332–341.
Yu. N. Zamataev, Yu. A. Kremnev, N. A. Grinenko and S. E. Podshibyakin, Russ. Med. Zh. [Russ. Med. J.], 2003, 9, 518–521 (in Russian).
M. S. Yunusov, Russ. Chem. Bull. Int. Ed., 2011, 60, 633–638.
S. N. Wright, Mol. Pharmacol., 2001, 59, 183–192.
N. E. Polyakov, V. K. Khan, M. B. Taraban, T. V. Leshina, O. A. Luzina, N. F. Salakhutdinov and G. A. Tolstikov, Org. Biomol. Chem., 2005, 3, 881–885.
F. I. Ataullahanov and A. M. Jabotinsky, Biophysics, 1975, 20, 596–601.
E. A. Khramtsova, D. V. Sosnovsky, A. A. Ageeva, E. Nuin, M. L. Marin, P. A. Purtov, S. S. Borisevich, S. L. Khursan, H. D. Roth, M. A. Miranda, V. F. Plyusnin and T. V. Leshina, Phys. Chem. Chem. Phys., 2016, 18, 12733–12741.
N. E. Polyakov and T. V. Leshina, Russ. Chem. Bull. Int. Ed., 2007, 56, 631–642.
N. E. Polyakov, T. V. Leshina, A. V. Tkachev, I. A. Nikitina and N. A. Pankrushina, J. Photochem. Photobiol., A, 2008, 197, 290–294.
N. E. Polyakov, O. A. Simaeva, M. B. Taraban, T. V. Leshina, T. A. Konovalova, L. D. Kispert, I. A. Nikitina, N. A. Pankrushina and A. V. Tkachev, J. Phys. Chem. B, 2010, 114, 4646–4651.
A. A. Schlotgauer, V. I. Klimentiev, V. S. Kornievskaya, N. E. Polyakov, A. A. Stepanov, S. F. Vasilevsky and T. V. Leshina, Appl. Magn. Reson., 2015, 46, 559–573.
E. C. Clark and V. Aronov, Pestic. Sci., 1996, 47, 355–362.
A. Beeby and A. E. Jones, J. Photochem. Photobiol., B, 2000, 72, 10–15.
A. Beeby and A. E. Jones, J. Photochem. Photobiol., B, 2001, 64, 109–116.
R. Staudmayer and T. D. Roberts, Tetrahedron Lett., 1974, 13, 1141–1144.
S. K. Jain and N. K. Jain, Int. J. Cosmet. Sci., 2010, 32, 89–98.
J. L. Belant, S. W. Gabrey, R. A. Dolbeer and T. W. Seamans, Crop Prot., 1995, 14, 171–175.
S. A. Osadchii, N. A. Pankrushina, M. M. Shakirov, E. E. Shults and G. A. Tolstikov, Russ. Chem. Bull., 2000, 3, 557–562.
N. A. Pankrushina, I. A. Nikitina, N. V. Anferova, S. A. Osadchii, M. M. Shakirov, E. E. Shults and G. A. Tolstikov, Russ. Chem. Bull. Int. Ed., 2003, 52, 2490–2499.
A. A. Stepanov, S. F. Vasilevsky and G. A. Tolstikov, Chem. Sustainable Dev., 2010, 8, 505–510.
H. E. Ungnade, J. Am. Chem. Soc., 1954, 76, 5133–5135.
S. S. Ostakhov, E. M. Tsyrlina, S. G. Yunusova, M. S. Yunusov and V. P. Kazakov, Russ. Chem. Bull., 1997, 46, 705–707.
H. Shimada, A. Nakamura, T. Yoshihara and S. Tobita, Photochem. Photobiol. Sci., 2005, 4, 367–375.
B. Tashkhodzhaev, Chem. Nat. Compd., 2010, 46, 421–425.
Acknowledgements
This work was supported by the grant 16-33-00412 of the Russian Foundation of Basic Research.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Open Access This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 License, which permits any non-commercial use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made.
The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder.
To view a copy of this licence, visit http://creativecommons.org/licenses/by-nc/3.0/.
About this article
Cite this article
Ageeva, A.A., Khramtsova, E.A., Plyusnin, V.F. et al. A photochemical approach for evaluating the reactivity of substituted lappaconitines. Photochem Photobiol Sci 17, 192–199 (2018). https://doi.org/10.1039/c7pp00366h
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c7pp00366h