Skip to main content
SpringerLink
Log in

Daunorubicin glycoconjugates with natural galectin ligands

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

Abstract

Conjugation of daunorubicin (1) with spacered N-β-glycosides of lactose containing from one to three oligosaccharide moieties, lacto-N-tetraose, and melibiose, was carried out. The synthesis was conducted via N-monoalkylation of hydrochloride 1 in aqueous DMF in the presence of NaHCO3 by treatment with bromoacetyl derivatives of oligosaccharide N-glycosides: β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2NHCOCH2Br, (β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2)2N(COCH2NH)2COCH2Br, (β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2)2NCOCH2-(β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2)N(COCH2NH)2COCH2Br, β-d-Galp-(1→3)-β-d-GlcpNAc-(1→3)-β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2NHCOCH2Br, α-d-Galp-(1→6)-β-d-Glcp-NHCOCH2NHCOCH2Br. The corresponding daunorubicin glycoconjugates were obtained as hydrochlorides in ∼40% yields.

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. E. N. Olsufyeva, A. N. Tevyashova, I. D. Trestchalin, M. N. Preobrazhenskaya, D. Platt, A. Klyosov, Carbohydr. Res., 2003, 338, 1359; DOI: https://doi.org/10.1016/s0008-6215(03)00181-2.

    Article  CAS  Google Scholar 

  2. A. N. Tevyashova, E. N. Olsuf’eva, M. N. Preobrazhenskaya, A. A. Klesov, E. Zomer, D. Platt, Russ. J. Bioorg. Chem., 2007, 33, 139; DOI: https://doi.org/10.1134/S1068162007010153.

    Article  CAS  Google Scholar 

  3. A. J. Domb, S. Benita, I. Polacheck, G. Linden, U. S. Pat., 2000, 6,011,008.

  4. A. K. Ghosh, S. Khan, F. Marini, J. A. Nelson, D. Farquhar, Tetrahedron Lett., 2000, 41, 4871; DOI: https://doi.org/10.1016/S0040-4039(00)00742-5.

    Article  CAS  Google Scholar 

  5. Trends Glycosci. Glycotechnol., a special issue “Recent Topics on Galectins”, 1997, No. 45, 1.

  6. R. Probstmeier, D. Montag, M. Schachner, J. Neurochem., 1995, 64, 2465; DOI: https://doi.org/10.1046/j.1471-4159.1995.64062465.x.

    Article  CAS  Google Scholar 

  7. M. C. Miller, J. P. Ribeiro, V. Roldós, S. Martín-Santamaría, F. J. Cañada, I. A. Nesmelova, S. André, M. Pang, A. A. Klyosov, L. G. Baum, J. Jiménez-Barbero, H.-J. Gabius, K. H. Mayo, Glycobiology, 2011, 21, 1627; DOI: https://doi.org/10.1093/glycob/cwr083.

    Article  CAS  Google Scholar 

  8. M. C. Miller, A. A. Klyosov, K. H. Mayo, Glycobiology, 2012, 22, 543; DOI: https://doi.org/10.1093/glycob/cwr173.

    Article  CAS  Google Scholar 

  9. A. Danguy, I. Camby, R. Kiss, Biochim. Biophys. Acta., 2002, 1572, 285; DOI: https://doi.org/10.1016/S0304-4165(02)00315-X.

    Article  CAS  Google Scholar 

  10. E. V. Moiseeva, E. M. Rapoport, N. V. Bovin, A. I. Miroshnikov, A. V. Chaadaeva, M. S. Krasilschikova, V. K. Bojenko, C. Bijleveld, J. E. van Dijk, W. van der Otter, Breast Cancer Res. Treat., 2005, 91, 227; DOI: https://doi.org/10.1007/s10549-005-0289-8.

    Article  CAS  Google Scholar 

  11. L. M. Likhosherstov, O. S. Novikova, N. G. Kolotyrkina, V. E. Piskarev, Russ. Chem. Bull., 2019, 68, 2339; DOI: https://doi.org/10.1007/s11172-019-2401-y.

    Article  CAS  Google Scholar 

  12. L. M. Likhosherstov, O. S. Novikova, A. O. Chizhov, I. B. Sivaev, V. I. Bregadze, Russ. Chem. Bull., 2011, 60, 2359; DOI: https://doi.org/10.1007/s11172-011-0362-x.

    Article  CAS  Google Scholar 

  13. R. T. Lee, Y. C. Lee, in Neoglycoconjugates: Preparation and Applications, Eds Y. C. Lee, R. T. Lee, Academic Press Inc., San Diego, California, 1994, 27–37.

  14. L. M. Likhosherstov, O. S. Novikova, L. O. Kononov, V. N. Shibaev, Russ. Chem. Bull., 2006, 55, 1262; DOI: https://doi.org/10.1007/s11172-006-0409-6.

    Article  CAS  Google Scholar 

  15. P. A. Belyakov, V. I. Kadentsev, A. O. Chizhov, N. G. Kolotyrkina, A. S. Shashkov, V. P. Ananikov, Mendeleev Commun., 2010, 20, 125; DOI: https://doi.org/10.1016/j.mencom.2010.05.01.

    Article  CAS  Google Scholar 

  16. L. M. Likhosherstov, O. S. Novikova, N. G. Kolotyrkina, V. E. Piskarev, Russ. Chem. Bull., 2019, 68, 411; DOI: https://doi.org/10.1007/s11172-019-2401-y.

    Article  CAS  Google Scholar 

  17. L. M. Likhosherstov, O. S. Novikova, A. O. Zheltova, V. N. Shibaev, Russ. Chem. Bull., 2000, 49, 1454; DOI: https://doi.org/10.1007/BF02495096.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    L. M. Likhosherstov & N. G. Kolotirkina

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

    V. E. Piskarev

Authors
  1. L. M. Likhosherstov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. G. Kolotirkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. E. Piskarev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. M. Likhosherstov.

Ethics declarations

The authors declare no competing interests.

Additional information

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation.

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 572–576, March, 2022.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Likhosherstov, L.M., Kolotirkina, N.G. & Piskarev, V.E. Daunorubicin glycoconjugates with natural galectin ligands. Russ Chem Bull 71, 572–576 (2022). https://doi.org/10.1007/s11172-022-3450-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3450-1

Key words

Search

Navigation