Skip to main content
Log in

Antioxidants Based on Covalently and Ionically Bound Trolox Conjugates

  • Published:
Chemistry of Natural Compounds Aims and scope

Three types of trolox dimers (bis-trolox derivatives), two of which were pairs of trolox molecules bound symmetrically through an ethylenediamine linker with covalent or ionic bonds and one of which was an asymmetric ionic–covalent conjugate, were synthesized. The water-solubility and antioxidant activity were measured for the synthesized compounds.

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. J. Lee, H.-N. Kim, D. Yang, K. Jung, H.-M. Kim, H.-H. Kim, H. Ha, and Z. H. Lee, J. Biol. Chem., 284 (20), 13725 (2009); J. A. Hyatt, Synth. Commun., 38, 8 (2008); K. Nakagawa-Goto, K. Yamada, S. Nakamura, T.-H. Chen, P.-C. Chiang, K. F. Bastow, S.-C. Wang, B. Spohn, M.-C. Hung, F.-Y. Lee, F.-C. Lee, and K.-H. Lee, Bioorg. Med. Chem. Lett., 17, 5204 (2007).

  2. S. L. Stvolinsky, E. R. Bulygina, T. N. Fedorova, K. Meguro, T. Sato, O. V. Tyulina, H. Abe, and A. A. Boldyrev, Cell. Mol. Neurobiol., 30, 395 (2010); Y. Catel, F. Aladedunye, and R. Przybylski, J. Agric. Food Chem., 58, 11081 (2010); V. R. Khairullina, A. Ya. Gerchikov, A. B. Safarova, R. R. Khalitova, A. Yu. Spivak, E. R. Shakurova, and V. N. Odinokov, Kin. Catal., 52 (2), 186 (2011); S. Dikalov and D. G. Harrison, in: Antioxidants and Cardiovascular Disease, 2nd Ed., M. G. Bourassa and J.-C. Tardif (eds.), Springer, 2006, pp. 167–194.

  3. J.-M. Contreras and W. Sippl, in: The Practice of Medicinal Chemistry, 3rd Ed., C. G. Wermuth (ed.), Elsevier, 2008, pp. 380–414.

  4. S. Stvolinsky, K. Toropova, M. Gordeeva, V. Kazey, T. Sato, K. Meguro, and A. Boldyrev, Amino Acids, 43, 165 (2012); S. M. Ahn, H. S. Rho, H. S. Baek, Y. H. Joo, Y. D. Hong, S. S. Shin, Y. Park, and S. N. Park, Bioorg. Med. Chem. Lett., 21, 7466 (2011); K. Shimizu, R. Kondo, K. Sakai, N. Takeda, T. Nagahata, and T. Oniki, Lipids, 36 (12), 1321 (2001); A. Yu. Spivak, R. R. Mufazzalova, E. R. Shakurova, and V. N. Odinokov, Zh. Org. Khim., 46 (9), 1355 (2010).

  5. Yu. V. Yushkova, E. I. Chernyak, Yu. F. Polienko, Yu. V. Gatilov, S. V. Morozov, and I. A. Grigor’ev, Chem. Nat. Compd., 49, 253 (2013).

  6. H. Fonge, S. K. Chitneni, J. Lixin, K. Vunckx, K. Prinsen, J. Nuyts, L. Mortelmans, G. Bormans, Y. Ni, and A. Verbruggen, Bioconjugate Chem., 18, 1924 (2007).

    Article  CAS  Google Scholar 

  7. M. Koufaki, A. Detsi, E. Theodorou, C. Kiziridi, T. Calogeropoulou, A. Vassilopoulos, A. P. Kourounakis, E. Rekka, P. N. Kourounakis, C. Gaitanaki, and P. Papazafiri, Bioorg. Med. Chem., 12, 4835 (2004).

    Article  CAS  PubMed  Google Scholar 

  8. G. Socrates, Infrared Characteristic Group Frequencies: Tables and Charts, 2nd Ed., Wiley, New York, 1994, p. 249.

    Google Scholar 

  9. M. Gorecki, A. Suszczynska, M. Woznica, A. Baj, M. Wolniak, M. K. Cyranski, S. Witkowski, and J. Frelek, Org. Biomol. Chem., 12, 2235 (2014).

    Article  CAS  PubMed  Google Scholar 

  10. O. D. Jankowski, K. E. Wesson, et al., US Pat. Appl. No. 20090118257 A1, May 7, 2009.

  11. H. Gunther, NMR Spectroscopy: Basic Principles, Concepts and Applications in Chemistry, 3rd Ed., 2013; ISBN: 978-3-527-33004-1, p. 734.

  12. RF State Pharmacopoeia, XIIth Ed., Moscow, 2007, p. 92.

  13. Y. Catel, F. Aladedunya, and R. Przybylski, J. Agric. Food Chem., 58, 11081 (2010).

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgment

Spectra of the synthesized compounds were obtained at the Khimiya CCU, SB, RAS. We thank Cand. Chem. Sci. A. M. Genaev for discussing the spectral data and Cand. Chem. Sci. N. I. Tkacheva for information support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. V. Yushkova.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2015, pp. 922–925.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yushkova, Y.V., Chernyak, E.I., Morozov, S.V. et al. Antioxidants Based on Covalently and Ionically Bound Trolox Conjugates. Chem Nat Compd 51, 1070–1073 (2015). https://doi.org/10.1007/s10600-015-1494-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-015-1494-2

Keywords

Navigation