SpringerLink
Log in

Cascade Synthesis of 1,4-Butanediol Monomesylate Glycoconjugates: Anticancer Candidates for Leukemia

  • Published:
Pharmaceutical Chemistry Journal Aims and scope

Acascade synthesis protocol for glycosides of 1,4-butanediol monomesylate, as anticancer drug candidates, is proposed. All obtained compounds are characterized by FT-IR, 1H and 13C NMR spectroscopy technique after separation by column chromatography. Cytotoxicity of the obtained glucosides and galactosides of 1,4-butanediol monomesylate on K562 human erythroleukemia cell line and normal peripheral blood mononuclear cells (PBMCs) is also investigated. Compared to the commercial anticancer drugs such as busulfan and doxorubicin, these compounds indicate promising results against the test cells. It is suggested that these new anticancer agents can be a potential replacement for the current drugs since they have relatively convenient synthetic procedure and higher effectiveness.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. B. L. Sorg, W. E. Hull, H-C. Kliem, et al., Carbohydr. Res., 340, 181 – 189 (2005).

    Article  CAS  Google Scholar 

  2. G. M. Dubowchik and M. A. Walker, Pharm. Ther., 83, 67 – 123 (1999).

    Article  CAS  Google Scholar 

  3. V. P. Torchilin, Eur. J. Pharm. Sci., 11, 81 – 91 (2000).

    Article  Google Scholar 

  4. L. G. Strauss and P. S. Conti, J. Nucl. Med., 32, 623 – 648 (1991).

    CAS  PubMed  Google Scholar 

  5. K. D. Bagshawe, Cell. Biophys., 24, 83 – 91 (1994).

    Article  Google Scholar 

  6. A. Pałasz, D. Cież, B. Trzewik, et al., Top. Curr. Chem., 377, 19 (2019).

    Article  Google Scholar 

  7. A. Diez-Sampedro, M. P. Lostao, E. M. Wright, and B. A. Hirayama, J. Membr, Biol., 176, 111 – 117 (2000).

    Article  CAS  Google Scholar 

  8. J. Pohl, B. Bertram, P. Hilgard, et al., Cancer. Chemother. Pharmacol., 35, 364 – 370 (1995).

    Article  CAS  Google Scholar 

  9. E. Briasoulis, I. Judson, N. Pavlidis, et al., J. Clin. Oncol., 18, 3535 – 3544 (2000).

    Article  CAS  Google Scholar 

  10. T. E. Ciuleanu, A. V. Pavlovsky, G. Bodokry, et al., Eur. J. Cancer., 45, 1589 – 1596 (2009).

    Article  CAS  Google Scholar 

  11. L. F. Tietze, J. Marian von Hof, B. Krewer, et al., Chem. Med. Chem., 3, 1946 – 1955 (2008).

    Article  CAS  Google Scholar 

  12. K. D. Bagshawe, Cell. Biophys., 24, 83 – 91 (1994).

    Article  Google Scholar 

  13. A. Guerrero, R. Guiho, N. Herranz, et al., Aging Cell., 19, e13133 (2020).

    Article  CAS  Google Scholar 

  14. K. N. Syrigos, G. Rowlinson-Busza, and A. A. Epenetos, Int. J. Cancer., 78, 712 – 719 (1998).

    Article  CAS  Google Scholar 

  15. I. Buggia, F. Locatelli, M. R. Regazzi, and M. Zecca, Ann. Pharmacother., 28, 1055 – 1062 (1994).

    Article  CAS  Google Scholar 

  16. M. Pishnamazi, S. Zabihi, S. Jamshidian, et al., J. Mol. Liq., 317, 113954 (2020).

    Article  CAS  Google Scholar 

  17. D. Kawashima, M. Asai, K. Katagiri, et al., Cell. Stress. Chaperon., 14, 535 – 543 (2009).

    Article  CAS  Google Scholar 

  18. K. Begna, A. Abdelatif, S. Schwager, et al., Blood. Cancer. J., 6, e427 (2016).

    Article  CAS  Google Scholar 

  19. S.-S. Lee, S-H. Jung, Y. R. Do, et al., Yonsei. Med. J., 61, 452 – 459 (2020).

    Article  CAS  Google Scholar 

  20. M.W. N. Deininger, J. M. Goldman, and J. V. Melo, Blood., 96, 3343 – 3356 (2000).

    Article  CAS  Google Scholar 

  21. C. M. Zwaan, G. J. L. Kaspers, R. Pieters, et al., Blood., 99, 245 – 251 (2002).

    Article  CAS  Google Scholar 

  22. C. Oslakovic, The Regulation of Blood Coagulation by High- Density Lipoprotein articles, Lund University (2010), No. 67.

  23. C. B. Andreasen and K. S. Latimer, Avian Dis., 33, 163 – 167 (1989).

    Article  CAS  Google Scholar 

  24. N. Singh, J. Kaur, P. Kumar, et al., Parasitol. Res., 105, 1317 – 1325 (2009).

    Article  Google Scholar 

  25. K. S. Korgaonkar and S. S. Ranade, Can. J. Microbiol., 12, 185 – 190 (1966).

    Article  CAS  Google Scholar 

  26. H. L. Bank, In Vitro Cell. Dev. Biol. Plant., 24, 266 – 273 (1988).

    Article  CAS  Google Scholar 

  27. B. Helferich and J. Werner, Chem. Ber., 75B, 1446 – 1452 (1942).

    Article  CAS  Google Scholar 

  28. C. E. Redemann and C. Niemann, Org. Synth., 22, 1 (1942).

    Article  CAS  Google Scholar 

  29. J. P. Praly and G. Descotes, Tetrahedron Lett., 23, 849 – 852 (1982).

    Article  CAS  Google Scholar 

  30. G. Zemplén and A. Kunz, Ber. Dtsch. Chem. Ges., 56, 1705 – 1710 (1923).

    Article  Google Scholar 

  31. J. C. Stockert, R. W. Horobin, L. L. Colombo, and A. Blázquez- Castro, Acta. Histochem., 120, 159 – 167 (2018).

    Article  CAS  Google Scholar 

  32. N. Noroozi Pesyan, H. Rashidnejad, M. A. Esmaeili, E. Safari, T. Tunç, M. Alilou, R. Safavi-Sohi, E. Şahin, J. Chin. Chem. Soc., 67, 1679 – 1695 (2020).

    Article  CAS  Google Scholar 

  33. A. Bahuguna, I. Khan, V. K. Bajpai, and S. C. Kang, Bangladesh J. Pharmacol., 12, 115 – 118 (2017).

    Article  Google Scholar 

  34. S. Aykul and E. Martinez-Hackert, Anal. Biochem., 508, 97 – 103 (2016).

    Article  CAS  Google Scholar 

  35. F. Denizot and R. Lang, J. Immunol. Methods., 89, 271 – 277 (1986).

    Article  CAS  Google Scholar 

  36. L. L.-Y. Chan, T. Smith, K. A. Kumph, et al., Cytotechnology, 68, 2015 – 2025 (2016).

    Article  Google Scholar 

  37. N. A. Samad, A. B. Abdul, R. Abdullah, et al., Int. J. Pharm. Pharm. Sci., 7, 298 – 302 (2015).

    CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the Urmia University and Urmia University of Medical Science for supporting this work.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, 57159, Iran

    Hamid Rashidnejad, Mohammad Anvar Kordi & Nader Noroozi Pesyan

  2. Department of Medicinal Chemistry, School of Pharmacy, Urmia University of Medical Sciences, Urmia, Iran

    Maryam Allahyari-devin

  3. Department of Immunology, Faculty of Veterinary Medicine, Urmia University, Urmia, Iran

    Alireza Hajabbas Frashchi

  4. Department of Chemistry and Biotechnology, Faculty of Science, Engineering and Technology, Swinburne University of Technology, Hawthorn, VIC, 3122, Australia

    Mohammad Ramezanitaghartapeh

Authors
  1. Hamid Rashidnejad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad Anvar Kordi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nader Noroozi Pesyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Maryam Allahyari-devin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alireza Hajabbas Frashchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Mohammad Ramezanitaghartapeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nader Noroozi Pesyan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rashidnejad, H., Kordi, M.A., Pesyan, N.N. et al. Cascade Synthesis of 1,4-Butanediol Monomesylate Glycoconjugates: Anticancer Candidates for Leukemia. Pharm Chem J 55, 1177–1183 (2022). https://doi.org/10.1007/s11094-022-02555-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-022-02555-9

Keywords

Search

Navigation