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Russian Chemical Bulletin

, Volume 67, Issue 4, pp 768–773 | Cite as

The complex of zinc with N-(5,6-dihydro-4H-1,3-thiazine-2-yl)benzamide

  • T. P. Trofimova
  • M. A. Orlova
  • A. V. Severin
  • E. S. Shalamova
  • A. N. Proshin
  • A. P. Orlov
Full Article
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Abstract

A complex of zinc with N-(5,6-dihydro-4H-1,3-thiazin-2-yl)benzamide (L) ligand, LZnCl2, was synthesized for subsequent medical trials. The molar extinction coefficients were determined for LHBr solutions in water and physiological saline, and for LZnCl2 ethanol solution. The ligand stability in various solvents was evaluated and the value of its protonation constant was found for the physiological saline solution, logK = 5.3±0.2. The impossibility of determination of the complex stability constant by the potentiometric titration method was demonstrated. The complex exhibited an insufficient stability in aqueous and physiological saline solutions, but was stable as the solution in alcohol. There was no sorption observed upon the treatment of ligand with hydroxyapatite nanoparticles, which could be a potential carrier for the therapeutic form of LZnCl2, providing additional degrees of freedom for the interaction of ligand with cell membranes and a prolonged action of zinc ions.

Key words

dihydrotiazine derivatives zinc complex stability protonation constant sorption on hydroxyapatite 

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References

  1. 1.
    L. Z. Z. Consolo, P. Melnikov, F. Z. Consolo, V. A. Nas cimento, J. C. D. V. Pontes, Eur. J. Clin. Nutr., 2013, 67, 1056.CrossRefGoogle Scholar
  2. 2.
    Y. Du, D. Guo, Q. Wu, D. Liu, H. Bi, Biol. Trace Elem. Res., 2014, 159,425.CrossRefGoogle Scholar
  3. 3.
    M. A. Orlova, E. Yu. Osipova, S. A. Roumiantsev, Br. J. Med. Med. Res., 2012, 2,21.CrossRefGoogle Scholar
  4. 4.
    G. Morgan, Med. Hypoth., 2005, 64,661.CrossRefGoogle Scholar
  5. 5.
    D. Taubert, R. Berkels, N. Grosser, H. Shreder, D. Gründemann, E. Schömig, Br. J. Pharmacol., 2004, 143,159.CrossRefGoogle Scholar
  6. 6.
    J. Valentova, R. Horakova, A. Lesova, E. Hostynova, J. Sokolik, Farm. Obzor, 2000, 69,40.Google Scholar
  7. 7.
    A. P. Orlov, M. A. Orlova, T. P. Trofimova, E. Yu. Osipova, A. N. Proshin, Russ. Chem. Bull., 2016, 65, 1879.CrossRefGoogle Scholar
  8. 8.
    J. R. Allan, J. Gavin, J. Term. Anal., 1980, 18,263.CrossRefGoogle Scholar
  9. 9.
    P. Lemoine, B. Viossat, N. H. Dung, A. Tomas, G. Morgant, F. Greenaway, J. R. J. Sorenson, Inorg. Biochem., 2004, 98, 1734.CrossRefGoogle Scholar
  10. 10.
    N. J. Brownless, D. A. Edwards, M. F. Mahon, Inorg. Chim. Acta, 1999, 287,89.CrossRefGoogle Scholar
  11. 11.
    T. Hokelek, H. Necefoglu, Analyt. Sci., 2001, 17, 1241.CrossRefGoogle Scholar
  12. 12.
    M. Olczak-Kobza, A. Mrozek, J. Therm. Anal. Calorim., 2009, 96,553.CrossRefGoogle Scholar
  13. 13.
    Y. Wang, M. Odoko, N. Okabe. Acta Crystallogr., C, 2004, 60, m479.CrossRefGoogle Scholar
  14. 14.
    X. Zhou, J. Du, S. Xiao, D. Ye, W. Dong, D. An, R. Zhang, Z. Zhou, J. Coord. Chem., 2014, 67, 2470.CrossRefGoogle Scholar
  15. 15.
    M. M. Rasulov, K. A. Abzaeva, M. I. Yakhkind, I. V. Zhigacheva, I. S. Nikolaeva, R. M. Rasulov, M. G. Voronkov, Russ. Chem. Bull., 2015, 64, 1686.CrossRefGoogle Scholar
  16. 16.
    S. Adisakwattana, W. Sompong, A. Meeprom, S. Ngamukote, S. Yibchokanun, Int. J. Mol. Sci., 2012, 13, 1778.CrossRefGoogle Scholar
  17. 17.
    S. T. Hafeez, S. Ali, M. N. Tahir, M. Iqbal, K. S. Munawar, J. Coordin. Chem., 2014, 67, 2479.CrossRefGoogle Scholar
  18. 18.
    F. J. Barros-Garcia, A. Bernalte-Garcila, A. M. Lozano-Vila, F. Luna-Giles, J. A. Pariente, R. Pedrero-Marin, A. B. Rodriguez, J. Inorg. Biochem., 2006, 100, 1861.CrossRefGoogle Scholar
  19. 19.
    P. Torres-Garcia, E. Vinuelas-Zahinos, F. Luna-Giles, J. Espino, F. J. Barros-Garcia, Polyhedron, 2011, 30, 2627.CrossRefGoogle Scholar
  20. 20.
    G. Pelosi, Open Crystallogr. J., 2010, 3,16.CrossRefGoogle Scholar
  21. 21.
    H. Shen, H. Zhu, M. Song, Y. Tian, Y. Huang, H. Zheng, R. Cao, J. Lin, Z. Bi, W. Zhong, BMC Cancer, 2014, 14,629.CrossRefGoogle Scholar
  22. 22.
    A. Molter, G. N. Kaluderovic, H. Kommera, R. Paschke, T. Langer, R. Pottgen, F. Mohr, J. Organomet. Chem., 2012, 70,80.CrossRefGoogle Scholar
  23. 23.
    V. Zaharia, A. Ignat, B. Ngameni, V. Kuete, M. L. Moungang, N. Fokunang, M. Vasilescu, N. Palibroda, C. Cristea, L. Silaghi-Dumitrescu, B. T. Ngadjui, Med. Chem. Res., 2013, 22, 5670.CrossRefGoogle Scholar
  24. 24.
    N. R. Filipovic, S. Bjelogrlic, A. Marinkovic, T. Ž. Verbic, I. N. Cvijetic, M. Sencanski, M. Rodic, M. Vujcic, D. Sladic, Z. Strikovic, T. R. Todorovic, C. D. Muller. RSC Adv., 2015, 5, 95191.CrossRefGoogle Scholar
  25. 25.
    N. Ikeda, E. M. Novak, D. Maria, A. S. Velosa, R. M. S. Pereira, Chem.-Biol. Inter., 2015, 239,184.CrossRefGoogle Scholar
  26. 26.
    M. A. Orlova, T. P. Trofimova, S. V. Nikulin, A. P. Orlov, Mosc. Univ. Chem. Bull., 2016, 71,258.CrossRefGoogle Scholar
  27. 27.
    T. P. Trofimova, O. N. Zefirova, A. A. Mandrugin, V. M. Fedoseev, D. I. Peregud, M. N. Onufriev, N. V. Gulyaeva, S. Ya. Proskuryakov, Mosc. Univ. Chem. Bull., 2008, 63,274.CrossRefGoogle Scholar
  28. 28.
    M. A. Orlova, T. P. Trofimova, R. A. Aliev, A. P. Orlov, S. V. Nikulin, A. N. Proshin, S. N. Kalmykov, J. Radioanal. Nuc lear Chem., 2017, 311, 1177.Google Scholar
  29. 29.
    A. Schoberl, K.-H. Magosch, Liebigs Ann. Chem., 1970, 742,74.CrossRefGoogle Scholar
  30. 30.
    A. V. Severin, M. A. Orlova, E. S. Shalamova, T. P. Trofimova, I. A. Ivanov, Russ. Chem. Bull., 2017, 66,9.CrossRefGoogle Scholar
  31. 31.
    R. A. Colvin, W. R. Holmes, C. P. Fontainea, W. Maret, Metallomics, 2010, 2, 306CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • T. P. Trofimova
    • 1
    • 2
  • M. A. Orlova
    • 1
    • 2
  • A. V. Severin
    • 1
  • E. S. Shalamova
    • 1
  • A. N. Proshin
    • 3
  • A. P. Orlov
    • 1
  1. 1.Department of ChemistryM. V. Lomonosov Moscow State UniversityMoscow, Russian FederationRussia
  2. 2.D. Rogachev National Research Clinical Center of Pediatric Hematology, Oncology, and ImmunologyMoscow, Russian FederationRussia
  3. 3.Institute of Physiological Active Compounds of Russian Academy of SciencesChernogolovka, Moscow Region, Russian FederationRussia

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