Skip to main content
Log in

Nitrobenzoxadiazole derivatives as nitric oxide donors: ESR study using spin trapping

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

Abstract

The ability of nitrobenzoxadiazoles to induce the SOX-operon from a genetically engineered biosensor based on E. coli MG 1655 (pSoxS-lux) was confirmed by the fact of producing nitric oxide. The NO-donating properties of three nitrobenzoxadiazole derivatives bearing π-excessive carbo- and heterocycles were found by the ESR method using spin trapping. The yield of nitrogen(II) oxide was 17, 0.3, and 1.6%. Sodium sulfide accelerates the thiol-dependent transformation and increases the yield of nitric oxide to 27, 16, and 12%, respectively.

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.

Similar content being viewed by others

References

  1. P. G. Wang, T. B. Cai, N. Taniguchi, Nitric Oxide Donors: For Pharmaceutical and Biological Applications, Wiley-VCH, Weinheim, 2005, 407 pp.

    Book  Google Scholar 

  2. V. G. Granik, N. B. Grigor´ev, Oksid azota (NO). Novyi put´ k poisku lekarstv [Nitric Oxide (NO). Novel Route to Search for Drugs], Vuzovskaya Kniga, Moscow, 2004, 360 pp. (in Russian).

    Google Scholar 

  3. L. J. Ignarro, Nitric Oxide: Biology and Pathobiology, Academic Press, San Diego, CA, 2000, 1017 pp.

    Google Scholar 

  4. G. Cairo, S. Recalcat, Expert Rev. Mol. Med., 2007, 33,1.

    Google Scholar 

  5. H. Cruz-Ramos, G. Wu, J. Crack, M. N. Hufhes, C. Scott, A. J. Thomson, J. Green, R. K. Poole, The EMBO J., 2002, 21, 3235.

    Article  CAS  Google Scholar 

  6. I. Gusarov, E. Nudler, Proc. Nat. Acad. Sci. USA, 2005, 102, 13855.

    Article  CAS  Google Scholar 

  7. E. N. Frolov, A. F. Vanin, Biofizika [Sov. Biophysics], 1973, 18, 605 (in Russian).

    CAS  Google Scholar 

  8. J. Crack, L. J. Smith, M. R. Stapleton, J. Peck, N. J. Watmough, M. J. Buttner, R. S. Buxton, V. S. Oganesyan, A. J. Thomson, N. E. Le Brun, J. Am. Chem. Soc., 2011, 133, 1112.

    Article  CAS  Google Scholar 

  9. S. P. L. Cary, J. A. Winger, M. A. Marletta, Proc. Nat. Acad. Sci. USA, 2005, 102, 13064.

    Article  CAS  Google Scholar 

  10. H. Cerecetto, W. Porcal, Mini-Rev. Med. Chem., 2005, 5,57.

    Article  CAS  Google Scholar 

  11. C. Jovene, E. A. Chugunova, R. Goumont, Mini-Rev. Med. Chem., 2013, 13, 1089.

    Article  CAS  Google Scholar 

  12. G. Tappi, P. V. Forni, Ann. Chim. Appl., 1948, 38, 602; Chem. Abstr., 1951, 45, 9804.

    CAS  Google Scholar 

  13. G. Tappi, P. V. Forni, Farm. Sci. e tec. (Pavia), 1950, 5, 241; Chem. Abstr., 1950, 44, 9103.

    CAS  Google Scholar 

  14. US Pat. 3420654; Chem. Abstr., 1969, 70, 87818.

  15. R. Ferioli, G. C. Folco, C. Ferretti, A. M. Gasco, C. Medana, R. Fruttero, M. Civelli, A. Gasco, Br. J. Pharmacol., 1995, 114,816.

    Article  CAS  Google Scholar 

  16. V. A. Chistyakov, Yu. P. Semenyuk, P. G. Morozov, E. V. Prazdnova, V. K. Chmykhalo, E. Yu. Kharchenko, M. E. Kletskii, G. S. Borodkin, A. V. Lisovin, O. N. Burov, S. V. Kurbatov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 1369 [Izv. Akad. Nauk, Ser. Khim., 2015, 1369].

    Article  CAS  Google Scholar 

  17. E. V. Prazdnova, E. Y. Kharchenko, V. A. Chistyakov, Yu. P. Semenyuk, P. G. Morozov, S. V. Kurbatov, V. K. Chmyhalo, Biol. Med. (Aligarh), 2015, 7,2.

    Google Scholar 

  18. M. Feelish, E. Noack, H. Schroder, Eur. Heart J., 1988,57.

    Google Scholar 

  19. N. V. Pyatakova, Yu. V. Khropov, A. M. Churakov, N. I. Tarasova, V. A. Serezhenkov, A. F. Vanin, V. A. Tartakovsky, I. S. Severina, Biochemistry (Moscow) (Engl. Transl.), 2002, 67, 329 [Biokhimiya, 2002, 67, 396].

    Article  CAS  Google Scholar 

  20. O. N. Burov, M. E. Kletskii, N. S. Fedik, A. V. Lisovin, S. V. Kurbatov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 951 [Khim. Geterotsikl. Soedin., 2015, 51, 951].

    Article  CAS  Google Scholar 

  21. V. G. Granik, S. Yu. Ryabova, N. B. Grigoriev, Russ. Chem. Rev., 1997, 66,717.

    Article  Google Scholar 

  22. C. Csonka, T. Páli, P. Bencsic, A. Görbe, P. Ferdinandy, T. Csont, Br. J. Pharmacol., 2015, 172, 1620.

    Article  CAS  Google Scholar 

  23. M. Sako, S. Oda, S. Ohara, K. Hirota, Y. Maki, J. Org. Chem., 1998, 63, 6947.

    Article  CAS  Google Scholar 

  24. I. T. Schiefer, L. VandeVrede, O. Arancio, G. R. J. Thatcher, J. Med. Chem., 2012, 55, 3076.

    Article  CAS  Google Scholar 

  25. A. F. Vanin, N. A. Sanina, V. A. Serezhenkov, D. Sh. Burbaev, V. I. Lozinsky, S. M. Aldoshin, Nitric Oxide, 2007, 16,82.

    Article  CAS  Google Scholar 

  26. A. F. Vanin, Nitric Oxide, 2016, 54,15.

    Article  CAS  Google Scholar 

  27. E. I. Chazov, O. V. Rodnenkov, A. V. Zorin, V. L. Lakomkin, V. V. Gramovich, O. N. Vyborov, A. G. Dragnev, V. I. Kapelko, L. I. Buryachkovskaya, A. A. Abramov, V. P. Massenko, E. V. Arzamastsev, A. F. Vanin, Nitric Oxide, 2012, 26,148.

    Article  CAS  Google Scholar 

  28. V. Vitvitsky, P. K. Yadav, A. Kurthen, R. Banerjee, J. Biol. Chem., 2015, 290, 8310.

    Article  CAS  Google Scholar 

  29. R. Pietri, E. Roman-Morales, J. Lopez-Garriga, Antioxidants & Redox Signalong, 2011, 15,393.

    Article  CAS  Google Scholar 

  30. N. B. Grigor´ev, M. I. Kalinkina, G. V. Chechekin, V. B. Nikitin, G. N. Engalycheva, N. N. Belushkina, V. I. Levina, I. L. Dalinger, M. D. Mashkovskii, S. A. Shevelev, V. A. Litosh, M. V. Vener, I. S. Severina, M. É. Kaminka, A. P. Arzamastsev, V. G. Granik, Pharm. Chem. J. (Engl. Transl.), 1998, 32, No. 3, 127 [Khim.-Farm. Zh., 1998, 32, No. 3, 15].

    Article  Google Scholar 

  31. J. I. Toohey, A. J. L. Cooper, Molecules, 2014, 19, 12789.

    Article  Google Scholar 

  32. R. Wedmann, A. Zahl, T. E. Shubina, M. Durr, F. W. Heinemann, B. E. C. Bugenhagen, P. Burger, I. Ivanovic-Burmazovic, M. R. Filipovic, Inorg. Chem., 2015, 54, 9367.

    Article  CAS  Google Scholar 

  33. A. F. Vanin, S. V. Vasilyeva, D. A. Streltsova, V. D. Mikoyan, Appl. Magn. Reson, 2014, 45,375.

    Article  CAS  Google Scholar 

  34. B. A. Goodman, J. B. Raynor, J. Chem. Soc. (A), 1970, 2038.

    Google Scholar 

  35. C. C. Tsou, W. C. Chiu, C. H. Ke, J. C. Tsai, Y. M. Wang, M. H. Chiang, W. F. Liaw, J. Am. Chem. Soc., 2014, 136, 9424.

    Article  CAS  Google Scholar 

  36. V. A. Serezhenkov, I. S. Kuznetsov, T. I. Romantsova, M. I. Kuznetsova, A. F. Vanin, Biophysics (Engl. Transl.), 2011, 56, 1088 [Biofizika, 2011, 56, 1125].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. A. Serezhenkov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0076—0082, January, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Serezhenkov, V.A., Tkachev, N.A., Semenyuk, Y.P. et al. Nitrobenzoxadiazole derivatives as nitric oxide donors: ESR study using spin trapping. Russ Chem Bull 66, 76–82 (2017). https://doi.org/10.1007/s11172-017-1702-2

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1702-2

Keywords

Navigation