Skip to main content
Log in

Preparation and characterization of inclusion complexes of topotecan with sulfonatocalixarene

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

Inclusion complex of sulfonatocalix[4]arene (SC4A) with topotecan (TPT) was prepared, and its inclusion complexation behaviors, such as stoichiometry, complex stability constants, and inclusion mode, were investigated by means of UV/Vis spectroscopy, DSC, and 2D NMR. The obtained results show that the quinoline ring and the dimethylaminomethyl group of TPT can be efficiently encapsulated in SC4A, and the complex is more soluble than free TPT.

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.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Voloschin, A.D., Betensky, R., Wen, P.Y., Hochberg, F., Batchelor, T.: Topotecan as salvage therapy for relapsed or refractory primary central nervous system lymphoma. J. Neurooncol. 86, 211–215 (2008)

    Article  CAS  Google Scholar 

  2. Calabrese, C.R., Almassy, R., Barton, S., Batey, M.A., Calvert, A.H., Canan-Koch, S., Durkacz, B.W., Hostomsky, Z., Kumpf, R.A., Kyle, S., Li, J., Maegley, K., Newell, D.R., Notarianni, E., Stratford, I.J., Skalitzky, D., Thomas, H.D., Wang, L.-Z., Webber, S.E., Williams, K.J., Curtin, N.J.: Anticancer chemosensitization and radiosensitization by the novel poly (ADP-ribose) polymerase-1 inhibitor AG14361. J. Natl. Cancer Inst. 96, 56–67 (2004)

    Article  CAS  Google Scholar 

  3. Macdonald, J.S., Jacobson, J.L., Ketchel, S.J., Weiss, G., Taylor, S., Mills, G., Kuebler, J.P., Rivkin, S., Conrad, M.: A phase II trial of topotecan in esophageal carcinoma: a Southwest Oncology Group study (SWOG 9339). Invest. New Drugs 18, 199–202 (2000)

    Article  CAS  Google Scholar 

  4. Sehouli, J., Oskay-Oezcelik, G.: Current role and future aspects of topotecan in relapsed ovarian cancer. Curr. Med. Res. Opin. 25, 639–651 (2009)

    Article  CAS  Google Scholar 

  5. McGuire, W.P., Blessing, J.A., Bookman, M.A., Lentz, S.S., Dunton, C.J.: Topotecan has substantial antitumor activity as first-line salvage therapy in platinum-sensitive epithelial ovarian carcinoma: a gynecologic oncology group study. J. Clin. Oncol. 18, 1062–1067 (2000)

    CAS  Google Scholar 

  6. Beldner, M.A., Sherman, C.A., Green, M.R., Garrett-Mayer, E., Chaudhary, U., Meyer, M.L., Kraft, A.S., Montero, A.J.: Phase I dose escalation study of vinorelbine and topotecan combination chemotherapy in patients with recurrent lung cancer. BMC Cancer 7, 231 (2007)

    Article  Google Scholar 

  7. Nicum, S.J., O’Brien, M.E.R.: Topotecan for the treatment of small-cell lung cancer. Expert Rev. Anticancer Ther. 7, 795–801 (2007)

    Article  CAS  Google Scholar 

  8. Idris, T., Winter, R., Lang, U., Petru, E.: Topotecan-induced long-term remission of an advanced endometrial cancer after treatment with cisplatinum, an anthracycline and paclitaxel. Anticancer Res. 29, 1761–1762 (2009)

    CAS  Google Scholar 

  9. Tao, X., Hu, W., Ramirez, P.T., Kavanagh, J.J.: Chemotherapy for recurrent and metastatic cervical cancer. Gynecol. Oncol. 110, S67–S71 (2008)

    Article  CAS  Google Scholar 

  10. Gutsche, C.D.: Calixarenes. The Royal Society of Chemistry, Cambridge (1989)

    Google Scholar 

  11. Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J.: Calixarenes. Kluwer Academic Publishers, Dordrecht (2001)

    Google Scholar 

  12. Yang, W., Otto, D.P., Liebenberg, W., de-Villiers, M.M.: Effect of para-sulfonato-calix(n)arenes on the solubility, chemical stability, and bioavailability of a water insoluble drug nifedipine. Curr. Drug Discov. Technol. 5, 129–139 (2008)

    Article  CAS  Google Scholar 

  13. Yang, W., De Villiers, M.M.: Effect of 4-sulfonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic. AAPS J. 7, E241–E248 (2005)

    Article  CAS  Google Scholar 

  14. Yang, W., De Villiers, M.M.: Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes. J. Pharm. Pharmacol. 56, 703–708 (2004)

    Article  CAS  Google Scholar 

  15. Yang, W., De Villiers, M.M.: The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes. Eur. J. Pharm. Biopharm. 58, 629–636 (2004)

    Article  CAS  Google Scholar 

  16. Fernandes, S.A., Cabec, L.F., Marsaioli, A.J., de Paula, E.: Investigation of tetracaine complexation with beta-cyclodextrins and p-sulphonic acid calix[6]arenes by nOe and PGSE NMR. J. Incl. Phenom. Macrocycl. Chem. 57, 395–401 (2007)

    Article  CAS  Google Scholar 

  17. Millership, J.S.: A preliminary investigation of the solution complexation of 4-sulphonic calix[n]arenes with testosterone. J. Incl. Phenom. Macrocycl. Chem. 39, 327–331 (2001)

    Article  CAS  Google Scholar 

  18. Coleman, A.W., Jebors, S., Cecillon, S., Perret, P., Garin, D., Marti-Battle, D., Moulin, M.: Toxicity and biodistribution of para-sulfonato-calix[4]arene in mice. New J. Chem. 32, 780–782 (2008)

    Article  CAS  Google Scholar 

  19. Perret, F., Lazar, A.N., Coleman, A.W.: Biochemistry of the para-sulfonato-calix[n]arenes. Chem. Commun. 2425–2438 (2006)

  20. Paclet, M.-H., Rousseau, C.F., Campion, Y., Morel, F., Coleman, A.W.: An absence of non-specific immune response towards para-sulphonato-calix[n]arenes. J. Incl. Phenom. Macrocycl. Chem. 55, 353–357 (2006)

    Article  CAS  Google Scholar 

  21. Silva, E.D., Shahgaldian, P., Coleman, A.W.: Haemolytic properties of some water-soluble para-sulphonato-calix-[n]-arenes. Int. J. Pharm. 273, 57–62 (2004)

    Article  Google Scholar 

  22. Shinkai, S., Araki, K., Tsubaki, T., Arimura, T., Manabe, O.: New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes. J. Chem. Soc. Perkin Trans. 1, 2297–2299 (1987)

    Article  Google Scholar 

  23. Wang, K., Guo, D.-S., Zhang, H.-Q., Li, D., Zheng, X.-L., Liu, Y.: Highly effective binding of viologens by p-sulfonatocalixarenes for the treatment of viologen poisoning. J. Med. Chem. 52, 6402–6412 (2009)

    Article  CAS  Google Scholar 

  24. Da Silva, E., Coleman, A.W.: Synthesis and complexation properties towards amino acids of mono-substituted p-sulphonato-calix-[n]-arenes. Tetrahedron 59, 7357–7364 (2003)

    Article  CAS  Google Scholar 

  25. Liu, Y., Ma, Y.-H., Chen, Y., Guo, D.-S., Li, Q.: Molecular recognition thermodynamics of pyridine derivatives by sulfonatocalixarenes at different pH values. J. Org. Chem. 71, 6468–6473 (2006)

    Article  CAS  Google Scholar 

  26. Arena, G., Contino, A., Lombardo, G.G., Sciotto, D.: Water-soluble calix[6]arenes, characterization of 5,11,17,23,29,35-hexasulphonate-37,38,39,40,41,42-hexahydroxycalix[6]arene and thermodynamic study of proton complex formation. Thermochim. Acta 264, 1–11 (1995)

    Article  CAS  Google Scholar 

  27. Connors, K.A.: Binding Constants, the Measurements of Molecular Complex Stability. Wiley, New York (1987)

    Google Scholar 

  28. Montassier, P., Duchêne, D., Poelman, M.-C.: Inclusion complexes of tretinoin with cyclodextrins. Int. J. Pharm. 153, 199–209 (1997)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank 973 Program (2006CB932900) and NNSFC (20932004 and 20721062) for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu Liu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, GS., Zhang, HY., Ding, F. et al. Preparation and characterization of inclusion complexes of topotecan with sulfonatocalixarene. J Incl Phenom Macrocycl Chem 69, 85–89 (2011). https://doi.org/10.1007/s10847-010-9817-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-010-9817-1

Keywords

Navigation