Skip to main content
SpringerLink
Log in

Binding behavior of artemether/sulfobutyl ether β-cyclodextrin in solution and the solid state

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

An inclusion complex of the antimalarial artemether with sulfobutyl ether β-cyclodextrin was prepared, and its inclusion complexation behavior in solution, e.g., stoichiometry, apparent binding constant, and inclusion mode, was investigated by means of phase solubility diagrams, 1H NMR, and 2D NMR. In the solid state the complex was characterized by powder X-ray diffraction, thermal analysis, and scanning electron microscopy. The results showed that artemether could be efficiently encapsulated in the cyclodextrin cavity in aqueous solution to produce a complex that was more soluble than free artemether.

Graphical abstract

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Ridley RG (2002) Nature 415:686

    Article  CAS  Google Scholar 

  2. Klayman DL (1985) Science 228:1049

    Article  CAS  Google Scholar 

  3. Luo XD, Shen CC (1987) Med Res Rev 7:29

    Article  CAS  Google Scholar 

  4. Vangapandu S, Jain M, Kaur K, Patil P, Patel SR, Jain R (2007) Med Res Rev 27:65

    Article  CAS  Google Scholar 

  5. Uekama K, Hirayama F, Irie T (1998) Chem Rev 98:2045

    Article  CAS  Google Scholar 

  6. Loftsson T, Järvinen T (1999) Adv Drug Deliv Rev 36:59

    Article  Google Scholar 

  7. Loftsson T, Brewster MEJ (1996) J Pharm Sci 85:101

    Article  Google Scholar 

  8. Wenz G, Han BH, Müller A (2006) Chem Rev 106:782

    Article  CAS  Google Scholar 

  9. Irie T, Uekama K (1997) J Pharm Sci 86:147

    Article  CAS  Google Scholar 

  10. Okimoto K, Miyake M, Ohnishi N, Rajewski RA, Stella VJ, Irie T, Uekama K (1998) Pharm Res 15:1562

    Article  CAS  Google Scholar 

  11. Rajewski RA, Stella VJ (1996) J Pharm Sci 85:1142

    Article  CAS  Google Scholar 

  12. Jain AC, Adeyeye MC (2001) Int J Pharm 212:177

    Article  CAS  Google Scholar 

  13. Yang B, Lin J, Chen Y, Liu Y (2009) Bioorg Med Chem 17:6311

    Article  CAS  Google Scholar 

  14. Higuchi T, Connors K (1965) Adv Anal Chem Instrum 4:117

    CAS  Google Scholar 

  15. Yang B, Yang LJ, Lin J, Chen Y, Liu Y (2009) J Inclusion Phenom Macrocyclic Chem 64:149

    Article  CAS  Google Scholar 

  16. Qi Q, Tucker E, Christian SD (2002) J Inclusion Phenom Macrocyclic Chem 43:213

    Article  Google Scholar 

  17. Correia I, Bezzenine N, Ronzani N, Platzer N, Beloeil JC, Doan BT (2002) J Phys Org Chem 15:647

    Article  CAS  Google Scholar 

  18. de Araújo MVG, Vieira EKB, Lázaro GS, Conegero LS, Almeida LE, Barreto LS, da Costa NB, Gimeneza IF (2008) Bioorg Med Chem 16:5788

    Article  Google Scholar 

  19. Al-Marzouqi AH, Shehatta I, Jobe B, Dowaidar A (2005) J Pharm Sci 95:292

    Article  Google Scholar 

  20. de Araújo MVG, Vieira EKB, Lazaro GS, Conegero LS, Ferreira OP, Almeida LE, Barreto LS, Costa NB, Gimenez IF (2007) Bioorg Med Chem 15:5752

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by National Natural Science Foundation of China (NNSFC) (No. 21062009), and the Natural Science Foundation of Yunnan Province (No. 2009ZC045M), which are gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Engineering, Faculty of Life Science and Technique, Kunming University of Science and Technique, Kunming, 650224, People’s Republic of China

    Bo Yang, Jing Wang, Yu-Lin Zhao & Jian Yang

  2. Experimental Center, Yunnan University, Kunming, 650091, People’s Republic of China

    Rong Huang

Authors
  1. Bo Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rong Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu-Lin Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jian Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bo Yang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, B., Wang, J., Huang, R. et al. Binding behavior of artemether/sulfobutyl ether β-cyclodextrin in solution and the solid state. Monatsh Chem 143, 235–241 (2012). https://doi.org/10.1007/s00706-011-0637-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0637-9

Keywords

Search

Navigation