Skip to main content
SpringerLink
Log in

Synthesis and antitumor activity of novel tetrakis[4-(closo-carboranylthio)tetrafluorophenyl]porphyrins

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Novel neutral and anionic fluorinated carboranylporphyrins for boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) were synthesized by the reaction of 5,10,15,20-pentafluorophenylporphyrin and its copper(II), zinc(II), and palladium(II) complexes with closo-mercaptocarboranes and cesium 1-mercapto-1-carba-closo-dodecaborate. Preliminary evaluation of biological activity reveals that anionic carboranylporphyrins are promising agents for BNCT and PDT.

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. T. D. Mody, J. Porphyrins Phthalocyanines, 2000, 4, 362.

    Article  CAS  Google Scholar 

  2. A. E. O’Connor, W. M. Gallagher, A. T. Byrne, Photochem. Photobiol., 2009, 85, 1053.

    Article  Google Scholar 

  3. T. J. Dougherty, J. Photochem. Photobiol., 1983, 38, 377.

    Article  CAS  Google Scholar 

  4. T. L. Phillips, Int. J. Rad. Oncol., 1994, 1215.

    Google Scholar 

  5. A. H. Soloway, W. Tjarks, B. A. Barnum, F. G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson, Chem. Rev., 1998, 98, 1515.

    Article  CAS  Google Scholar 

  6. R. L. Moss, App. Radiat. Isot., 2014, 88, 11.

    Google Scholar 

  7. V. I. Bregadze, I. B. Sivaev, D. Gabel, D. Wohrle, J. Porphyrins Phthalocyanines, 2001, 5, 767.

    Article  CAS  Google Scholar 

  8. V. A. Olshevskaya, A. V. Zaytsev, A. N. Savchenko, A. A. Shtil, C. S. Cheong, V. N. Kalinin, Bull. Korean Chem. Soc., 2007, 28, 1910.

    Article  CAS  Google Scholar 

  9. M. W. Renner, M. Miura, M. W. Easson, M. G. H. Vicente, Curr. Med. Chem. Anti-Cancer Agents, 2006, 6, 145.

    Article  CAS  Google Scholar 

  10. M. A. Grin, D. I. Brittal, A. G. Tsiprovskiy, V. I. Bregadze, A. F. Mironov, Macroheterocycles, 2010, 4, 222.

    Google Scholar 

  11. V. A. Ol’shevskaya, A. V. Zaitsev, Y. V. Dutikova, V. N. Luzgina, E. G. Kononova, P. V. Petrovsky, V. N. Kalinin, Macroheterocycles, 2009, 2, 221.

    Google Scholar 

  12. V. A. Ol’shevskaya, A. V. Zaitsev, A. L. Sigan, E. G. Kononova, P. V. Petrovsky, N. D. Chkanikov, V. N. Kalinin, Dokl. Chem. (Engl. Transl.), 2010, 435, 334.[Dokl. Acad. Nauk, 2010, 435, 755].

    Google Scholar 

  13. S. Purser, P. R. Moore, S. Swallowb, V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320–330.

    Article  CAS  Google Scholar 

  14. A. C. B. Figueira, O. T. Kleber, O. A. Serra, Dyes, Pigments, 2011, 91, 383.

    Article  CAS  Google Scholar 

  15. J. Tuexen, S. Eibenberger, S. Gerlich, M. Arndt, M. Mayor, Eur. J. Org. Chem., 2011, 4823.

    Google Scholar 

  16. J. F. B. Hall, X. Han, M. Poliakoff, R. A. Bourne, M. W. George, Chem. Commun., 2012, 48, 3073.

    Article  CAS  Google Scholar 

  17. J. P. C. Tome, M. G. P. M. S. Neves, A. C. Tome, J. A. S. Cavaleiro, A. F. Mendonca, I. N. Pegado, R. Duarte, M. L. Valdeira, Bioorg. Med. Chem., 2005, 13, 3878.

    Article  CAS  Google Scholar 

  18. J. Plešek, Z. Janoušek, S. He mánek, Collect. Czech. Chem. Commun., 1978, 43, 1332.

    Article  Google Scholar 

  19. J. Plešek, S. Heřmánek, Collect. Czech. Chem. Commun., 1981, 46, 687.

    Article  Google Scholar 

  20. E. Hao, E. Friso, G. Miotto, G. Jori, M. Soncin, C. Fabris, M. Sibrian-Vazquez, M. G. H. Vicente, Org. Biomol. Chem., 2008, 6, 3732.

    Article  CAS  Google Scholar 

  21. P. J. Spellane, M. Gouterman, A. Antipas, S. Kim, Y. C. Liu, Inorg. Chem., 1980, 19, 386.

    Article  CAS  Google Scholar 

  22. T. Jelínek, J. Plešek, S. Heřmánek, and B. Štíbr, Collect. Czech. Chem. Commun., 1986, 51, 819.

    Article  Google Scholar 

  23. L. N. Lysenkova, K. F. Turchin, A. M. Korolev, L. G. Dezhenkova, O. B. Bekker, A. A. Shtil, V. N. Danilenko, M. N. Preobrazhenskaya, Bioorg. Med. Chem., 2013, 21, 2918.

    Article  CAS  Google Scholar 

  24. M. M. Moisenovich, V. A. Ol’shevskaya, T. I. Rokitskaya, A. A. Ramonova, R. G. Nikitina, A. N. Savchenko, V. V. Tatarskiy, M. A. Kaplan, V. N. Kalinin, E. A. Kotova, O. V. Uvarov, I. I. Agapov, Y. N. Antonenko, A. A. Shtil, PLoS One, 2010, 5. e12717.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    V. A. Ol’shevskaya, A. V. Zaitsev & V. N. Kalinin

  2. N. N. Blokhin Cancer Research Center, Russian Academy of Medical Scieneces, 23 Kashirskoe shosse, 115478, Moscow, Russian Federation

    A. A. Shtil

Authors
  1. V. A. Ol’shevskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Zaitsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. N. Kalinin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Shtil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Ol’shevskaya.

Additional information

Dedicated to Academician of the Russian Academy of Sciences Yu. N. Bubnov on the occasion of his 80th birthday and the 60th anniversary of the foundation of A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2383–2387, October, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ol’shevskaya, V.A., Zaitsev, A.V., Kalinin, V.N. et al. Synthesis and antitumor activity of novel tetrakis[4-(closo-carboranylthio)tetrafluorophenyl]porphyrins. Russ Chem Bull 63, 2383–2387 (2014). https://doi.org/10.1007/s11172-014-0751-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-014-0751-z

Key words

Search

Navigation