Skip to main content
SpringerLink
Log in

Lipoylcarnosine: Synthesis, Study of Physico-Chemical and Antioxidant Properties, Biological Activity

  • Published:
Biochemistry (Moscow), Supplement Series B: Biomedical Chemistry Aims and scope Submit manuscript

Abstract—

Synthesis of lipoylcarnosine (LipС), a conjugated molecule based on two natural antioxidants, carnosine and α-lipoic acid, is described and its physico-chemical, antioxidant properties and biological activity are characterized. According to reversed-phase HPLC with a UV detector, purity of the final product was 89.3%. The individuality of the obtained sodium salt of LipС was confirmed by tandem HPLC-mass spectrometry. LipC demonstrated high resistance to hydrolysis with serum carnosinase. The antioxidant activity of LipC evaluated by the reaction with the formation of thiobarbituric acid reacting substances and kinetic parameters of iron-induced chemiluminescence was higher than that of carnosine and lipoic acid. LipC did not affect viability of SH-SY5Y human neuroblastoma cells, differentiated to the dopaminergic phenotype, at concentrations not exceeding 5 mM. In the concentration range of 0.1–0.25 mM LipC protected neuronal cells against 1-methyl-4-phenylpyridinium (MPP+)-induced toxicity.

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.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. Halliwell, B., Rafter, J., and Jenner, A., Am. J. Clin. Nutr., 2005, vol. 81, pp. 268S–276S.

    Article  CAS  PubMed  Google Scholar 

  2. Rizvi, S.I. and Jha, R., Expert. Opin. Drug. Discov., 2011, vol. 6, pp. 89–102.

    Article  CAS  PubMed  Google Scholar 

  3. Cross, C., Halliwell, B., Borish, E., Pryor, W., Ames, B., Saul, R., McCord, J., and Harman, D., Ann. Intern. Med., 1987, vol. 107, pp. 526–545.

    Article  CAS  PubMed  Google Scholar 

  4. Baldeiras, I., Santana, I., Proença, M.T., Garrucho, M.H., Pascoal, R., Rodrigues, A., Duro, D., and Oliveira, C.R., J. Alzheimer’s Dis., 2010, vol. 21, pp. 1165–1177.

    Article  CAS  Google Scholar 

  5. Reuter, S., Gupta, S.C., Chaturvedi, M.M., and Aggarwal, B.B., Free Radic. Biol. Med., 2010, vol. 49, pp. 1603–1616.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Feruzi, O., Miri, R., Tavakkoli, M., and Saso, L., Curr. Med. Chem., 2011, vol. 18, pp. 3871–3888.

    Article  Google Scholar 

  7. Boldyrev, A.A., Biochemistry (Moscow), 2012, vol. 77, pp. 403–418.

    Google Scholar 

  8. Boldyrev, A.A., Aldini, G., and Derave, W., Physiol. Rev., 2013, vol. 93, pp. 1803–1845.

    Article  CAS  PubMed  Google Scholar 

  9. Fedorova, T.N., Belyaev, M.S., Trunova, O.A., Gnezditskii, V.V., Maksimova, M.Yu., and Boldyrev, A.A., Biol. Membr. (Moscow), 2008, vol. 25, pp. 479–483.

    Google Scholar 

  10. Boldyrev, A., Fedorova, T., Stepanova, M., Dobrotvorskaya, I., Kozlova, E., Boldanova, N., Bagyeva, G., Ivanova-Smolenskaya, I., and Illarioshkin, S., Rejuvenation Res., 2008, vol. 11, pp. 821–827.

    Article  CAS  PubMed  Google Scholar 

  11. Margolis, F.L., Grillo, M., Grannot-Reisfeld, N., and Farbman, I., Biochim. Biophys. Acta, 1983, vol. 744, pp. 237–248.

    Article  CAS  PubMed  Google Scholar 

  12. Stvolinsky, S.L., Bulygina, E.R., Fedorova, T.N., Meguro, K., Sato, T., Tyulina, O.V., Abe, H., and Boldyrev, A.A., Cell. Mol. Neurobiol., 2010, vol. 30, pp. 395–404.

    Article  CAS  PubMed  Google Scholar 

  13. Goraca, A., Huk-Kolega, H., Piechota, A., Kleniewska, P., Ciejka, E., and Skibska, B., Pharmacol. Rep., 2011, vol. 63, pp. 849–858.

    Article  CAS  PubMed  Google Scholar 

  14. Bilska, A. and Wlodek, L., Pharmacol. Rep., 2005, vol. 57, pp. 570–577.

    CAS  PubMed  Google Scholar 

  15. Shay, K.P., Morea, R.F., Smith, E.J., Smith, A.R., and Hagen, T.M., Biochim. Biophys. Acta, 2009, vol. 1790, pp. 1149–1160.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Anti-Aging Complex (ALA/ALC/Carnosine/GSE). Ray & Terry’s Longevity Products © Copyright Ray and Terry’s Health Products Inc. All Rights Reserved, 2011. info@rayandterry.com.

  17. Giampapa, V., US Patent 20060269617 A1, 2006.

  18. Guasti, P.L., US Patent 20120129781 Al, 2013.

  19. Nativi, C., Ghelardini, C., Giancarlo La, M., and Dragoni, E. US Patent 20130072533A1, 2013.

  20. Nativi, C., Gualdani, R., Dragoni, E., Di CesareMannelli, L., Sostegni, S., Norcini, M., Gabrielli, G., la Marca, G., Richichi, B., Francesconi, O., Moncelli, M.R., Ghelardini, C., and Roelens, S. Sci. Reports, 2013, vol. 3. doi 10.1038/srep02005

  21. Antonova, N.A., Sorokoumova, G.M., Fedorova, T.N., Stvolinsky, S.L., Abaimov, D.A., Popenko, V.I., and Shvets, V.I., Tonkie Khimicheskie Tekhnologii, 2016, vol. 11, no. 6, pp. 55–62.

    CAS  Google Scholar 

  22. Pegova, A., Abe, H., and Boldyrev, A., Comp. Biochem. Physiol., part B, Biochem. Mol. Biol., 2000, vol. 127, pp. 443–446.

    Article  CAS  Google Scholar 

  23. Presgraves, S.P., Ahmed, T., Borwege, S., and Joyce, J.N., Neurotox. Res., 2004, vol. 5, pp. 579–598.

    Article  PubMed  Google Scholar 

  24. Pahlman, S., Ruusala, A.I., Abrahamsson, L., Mattsson, M.E., and Esscher, T., Cell Differ., 1984, vol. 14, pp. 135–144.

    Article  CAS  PubMed  Google Scholar 

  25. Scudiero, D.A., Shoemaker, R.H., Paull, K.D., Monks, A., Tierney, S., Nofziger, T.H., Currens, M.J., Seniff, D., and Boyd, M.R., Cancer Res., 1988, vol. 48, pp. 4827–4833.

    CAS  PubMed  Google Scholar 

  26. Sorokoumova, G.M., Selishcheva, A.A., and Kaplun, A.P., Fosfolipidy: Metody ikh vydeleniya, obnaruzheniya i izucheniya fiziko-khimicheskikh svoistv lipidnykh dispersyi v vode. Uchebnoe posobie po bioorganicheskoi khimii (Phospholipids: Methods of Their Isolation, Detection and Analysis of Physico-Chemical Lipid Dispersions in Water. A Handbook of Bioorganic Chemistry), Moscow: Moscow Technological University, 2001.

    Google Scholar 

  27. Fedorova, T.N., Eksper. Klin. Farmakol., 2003, vol. 66, no. 5, pp. 56–58.

    CAS  Google Scholar 

  28. Bellia, F., Vecchio, G., and Rizzarelli, E., Molecules, 2014, vol. 19, pp. 2299–2329.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Center of Neurology, Volokolamskoe shosse 80, 125367, Moscow, Russia

    S. L. Stvolinsky, O. I. Kulikova, A. V. Lopachev, D. A. Abaimov, O. M. Lopacheva & T. N. Fedorova

  2. Moscow Technological University, Moscow, 119454, Russia

    N. A. Antonova, I. Al-Baidani, A. P. Kaplun & G. M. Sorokoumova

  3. Peoples’ Friendship University of Russia, Moscow, 117198, Russia

    O. I. Kulikova

  4. Moscow State University, International Biotechnological Center, Moscow, Russia

    O. M. Lopacheva

Authors
  1. S. L. Stvolinsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. A. Antonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. I. Kulikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Lopachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. A. Abaimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. Al-Baidani
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. O. M. Lopacheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. T. N. Fedorova
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. A. P. Kaplun
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. G. M. Sorokoumova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. L. Stvolinsky.

Additional information

Translated by A. Medvedev

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Stvolinsky, S.L., Antonova, N.A., Kulikova, O.I. et al. Lipoylcarnosine: Synthesis, Study of Physico-Chemical and Antioxidant Properties, Biological Activity. Biochem. Moscow Suppl. Ser. B 12, 308–315 (2018). https://doi.org/10.1134/S199075081804008X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S199075081804008X

Keywords:

Search

Navigation