Skip to main content
SpringerLink
Log in

Furodihydroquinolines as Novel Photosensitizers for Photochemotherapy

  • ELEMENTARY PHYSICOCHEMICAL PROCESSES
  • Published:
Russian Journal of Physical Chemistry B Aims and scope Submit manuscript

Abstract

New derivatives of furodihydroquinoline (FDHQ) with substituents at the 5 position of the benzene ring have been synthesized, and their photophysical and photochemical properties have been studied. The triplet nature of short-lived states generated on photoexcitation of FDHQ has been shown with the use of pulse photolysis and triplet–triplet energy transfer to biscarbocyanine dye. Spectral and kinetic parameters of the triplet states for the synthesized FDHQ have been established. It has been shown that the FDHQ triplet state participates in the formation of the reactive oxygen species (ROS). Processes involving the FDHQ triplet state are important for PUVA-therapy and other processes of photochemotherapy.

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.

Similar content being viewed by others

REFERENCES

  1. D. Bethea, B. Fullmer, S. Syed, et al., J. Dermatol. Sci. 19, 78 (1999).

    Article  CAS  Google Scholar 

  2. Y. X. Wei, B. Sun, L. Xiao, et al., Transplant Proc. 50, 3906 (2018).

    Article  CAS  Google Scholar 

  3. T. C. Ling, T. H. Clayon, J. Crawley, et al., Braz. J. Dermatol. 174, 24 (2016).

    Article  CAS  Google Scholar 

  4. S. B. Pai and S. Shetty, Indian J. Dermatol. Venereol. Leprol. 81, 559 (2015).

    Article  Google Scholar 

  5. E. J. Yurkow and J. D. Laskin, Cancer Chemother. Pharmacol. 27, 315 (1991).

    Article  CAS  Google Scholar 

  6. J. Lauharanta, Clin. Dermatol. 15, 769 (1997).

    Article  CAS  Google Scholar 

  7. J. Krutmann, H. Hönigsmann, and C. A. Elmets, Dermatological Phototherapy and Photodiagnostic Methods, 2nd ed. (Springer, Berlin, 2009).

    Google Scholar 

  8. Z. Kuzmina, D. Stroncek, and S. Z. Pavletic, J. Clin. Apher. 30, 224 (2015).

    Article  Google Scholar 

  9. R. Knobler, G. Berlin, P. Calzavara-Pinton, et al., J. Eur. Acad. Dermatol. Venereol. 28, 1 (2014).

    Article  CAS  Google Scholar 

  10. N. Raquet and D. Schrenk, Chem. Res. Toxicol. 22, 1639 (2009).

    Article  CAS  Google Scholar 

  11. X. Chen, J. Kagan, F. Dall’Acqua, et al., J. Photochem. Photobiol. B. 22, 51 (1994).

    Article  CAS  Google Scholar 

  12. F. A. Derheimer, J. K. Hicks, M. T. Paulsen, et al., Mol. Pharmacol. 75, 599 (2009).

    Article  CAS  Google Scholar 

  13. C. Marzano, A. Chilin, F. Bordin, et al., Bioorg. Med. Chem. 10, 2835 (2002).

    Article  CAS  Google Scholar 

  14. A. Chilin, C. Marzano, A. Guiotto, et al., J. Med. Chem. 45, 1146 (2002).

    Article  CAS  Google Scholar 

  15. E. N. Khodot, V. A. Kuzmin, et al., RF Patent No. 2614248 (2016).

  16. O. N. Lygo, T. D. Nekipelova, E. N. Khodot, V. A. Kuzmin, V. V. Shakhmatov, V. A. Volnukhin, V. V. Vargin, A. B. Shevelev, and A. V. Shibaeva, High Energy Chem. 46, 171 (2012).

    Article  CAS  Google Scholar 

  17. T. D. Nekipelova, O. N. Lygo, E. N. Khodot, V. A. Kuzmin, V. V. Shakhmatov, V. V. Vargin, A. V. Belyakova, and M. V. Zyl’kova, High Energy Chem. 46, 166 (2012).

    Article  CAS  Google Scholar 

  18. O. N. Lygo, T. D. Nekipelova, E. N. Khodot, V. V. Shakhmatov, A. S. Kononikhin, E. N. Nikolaev, and V. A. Kuzmin, High Energy Chem. 46, 358 (2012).

    Article  CAS  Google Scholar 

  19. V. A. Kuzmin, L. I. Mazaletskaya, T. D. Nekipelova, and E. N. Khodot, Russ. Chem. Bull. 57, 2405 (2008).

    Article  CAS  Google Scholar 

  20. A. A. Kostyukov, T. D. Nekipelova, Yu. E. Borisevich, and V. A. Kuzmin, High Energy Chem. 53, 87 (2019).

    Article  CAS  Google Scholar 

  21. A. M. Brouwer, Pure Appl. Chem. 83, 2213 (2011).

    Article  CAS  Google Scholar 

  22. K. Suzuki, A. Kobayashi, S. Kaneko, et al., Phys. Chem. Chem. Phys. 11, 9850 (2009).

    Article  CAS  Google Scholar 

  23. L. D. Ramos, H. M. Da Cruz, and K. P. Morelli Frin, Photochem. Photobiol. Sci. 16, 459 (2017).

    Article  CAS  Google Scholar 

  24. R. Ruiz-Gonzalez, R. Zanocco, Y. Gidi, et al., Photochem. Photobiol. 89, 1427 (2013).

    Article  CAS  Google Scholar 

  25. F. Tanaka, T. Furuta, M. Okamoto, et al., Phys. Chem. Chem. Phys. 6, 1219 (2004).

    Article  CAS  Google Scholar 

  26. V. G. Plotnikov and A. A. Ovchinnikov, Russ. Chem. Rev. 47, 247 (1978).

    Article  Google Scholar 

  27. V. P. Sakun, A. I. Shushin, and E. M. Balashov, Russ. J. Phys. Chem. B. 11, 715 (2017).

    Article  CAS  Google Scholar 

  28. A. I. Shushin and V. P. Sakun, Russ. J. Phys. Chem. B. 10, 181 (2016).

    Article  CAS  Google Scholar 

  29. O. N. Lygo, I. V. Shelaev, F. E. Gostev, T. D. Nekipelova, E. N. Khodot, Yu. P. Tsentalovich, A. A. Titov, V. A. Kuzmin, and O. M. Sarkisov, High Energy Chem. 47, 230 (2013).

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMNTS

The spectral measurements were carried out in the Core Facility of IBCP RAS “New Materials and Technologies.”

Funding

The study was supported by the Russian Scientific Foundation, project no. 18-13-00463 “Mechanisms of Photochemical Processes in the Complexes of Polymethine Dyes with Two-conjugated Chromophores with Proteins.”

Author information

Authors and Affiliations

  1. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 119334, Moscow, Russia

    V. A. Kuzmin, V. A. Volnukhin, A. E. Egorov, O. N. Klimovich, A. A. Kostyukov, T. D. Nekipelova, E. N. Khodot, V. V. Shakhmatov, A. V. Shevelev, A. B. Shibaeva & A. A. Shtil

  2. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    E. N. Khodot

  3. Vavilov Institute of General Genetics, Russian Academy of Sciences, 119991, Moscow, Russia

    A. V. Shevelev

  4. Moscow Scientific and Practical Center of Dermatovenereology and Cosmetology, 119071, Moscow, Russia

    V. A. Volnukhin

Authors
  1. V. A. Kuzmin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Volnukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. E. Egorov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. N. Klimovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Kostyukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. T. D. Nekipelova
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. E. N. Khodot
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. V. V. Shakhmatov
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. A. V. Shevelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. A. B. Shibaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. A. A. Shtil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Kuzmin.

Additional information

Translated by T. Nekipelova

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kuzmin, V.A., Volnukhin, V.A., Egorov, A.E. et al. Furodihydroquinolines as Novel Photosensitizers for Photochemotherapy. Russ. J. Phys. Chem. B 13, 893–899 (2019). https://doi.org/10.1134/S199079311906023X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S199079311906023X

Keywords:

Search

Navigation