Skip to main content
SpringerLink
Log in

Spectroscopic study and antioxidant activity of the inclusion complexes of cyclodextrins and amlodipine besylate drug

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

Abstract

The aim of the study was to synthesize and characterization the inclusion complexes of amlodipine besylate (AML) drug with β-cyclodextrin (β-CD) and γ-cyclodextrin (γ-CD) which has antioxidating activity property. The guest/host interaction of AML with β-CD and γ-CD in order to complexation drug in β-CD and γ-CD were investigated. The interaction inclusion complexes was characterized by fourier transform infrared and ultraviolet–visible spectroscopies. The formation constant was calculated by using a modified Benesi–Hildebrand equation at 25 °C. The stoichiometry of inclusion complexes was found to be 1:1 for β-CD and γ-CD with AML drug. The antioxidant activity of AML drug and its inclusion complexes were determined by the scavenging of stable radical 2,2′-diphenyl-1-picrylhydrazyl (DPPH·). Kinetic studies of DPPH· with AML and CDs complexes were done. The experimental results confirmed the forming of AML complexes with CDs also these indicated that the AML/β-CD and AML/γ-CD inclusion complexes was the most reactive than its free form into antioxidant activity.

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
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. Helena, D.: Cyclodextrins and Their Complexes: 1. Molecules with Holes—Cyclodextrins. Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim (2006). ISBN 3-527-31280-3

  2. Ramnik, S., Nitin, B., Jyotsana, M., Hiremath, S.N.: Characterization of cyclodextrin inclusion complexes—a review. J. Pharm. Sci. Technol. 2(3), 171–183 (2010)

    Google Scholar 

  3. Thorsteinn, L., Marma, S., Marcuse, B.: Self association of cyclodextrins and cyclodextrin complexes. J. Pharm. Sci. 93, 1091–1099 (2004)

    Article  Google Scholar 

  4. Higuchi, T., Connors, K.A.: Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4, 117–212 (1965)

    CAS  Google Scholar 

  5. Loftsson, T., Jarho, P., Masson, M., Jarvinen, T.: Cyclodextrins in drug delivery. Expert Opin. Drug Deliv. 2, 335–351 (2005)

    Article  CAS  Google Scholar 

  6. Francisco, B.T., Pessine, A.C., Guilherme, L.A.: Review: cyclodextrin inclusion complexes probed by NMR techniques. J. Magn. Reson. Spectrosc. 237–264 (2012). ISBN 978-953-51-0065-2

  7. Mousavifard, B., Zeidabadinejad, L., Pourastarabadi, S., Dehestani, M.: Investigation of interaction of vanillin with Alpha, Beta and Gamma cyclodextrin as drug delivery carriers: brief report. Tehran Univ. Med. J. 73(2), 132–137 (2015)

    Google Scholar 

  8. Dhanaraju, M.D., Senthilkumarun, K., Baskaran, T., Sreeramamoorthy, M.: Enhancement of bioavailability of griseofulvine by its complexation with cyclodextrin. Drug Dev. Ind. Pharm. 24, 583–587 (1998)

    Article  CAS  Google Scholar 

  9. Snezana, S., Ilic, S., Vesna, D.N., Ljubisa, B.N., Aleksandar, S.Z., Agnes, J.K., Mirjana, M.P., Slobodan, D.P.: The improved photostability of naproxen in the inclusion complex with 2-hydroxypropyl-β-cyclodextrin. Hem. Ind. 69(4), 361–370 (2015)

    Article  Google Scholar 

  10. Gharibnaseri, N., Ashnagar, A., Husseini, F.: Study of the inclusion complexation of piroxicam–β-cyclodextrin and determination of the stability constant (K) by UV–visible spectroscopy. Sci. Iran. 14, 308–315 (2007)

    Google Scholar 

  11. Imran, Sh., Vishal, G., Abhay, J., Naveen, G.: Preparation and characterisation of B cyclodextrin aspirin inclusion complex. J. Pharm. Life Sci. (IJPLS) 2, 704–710 (2011)

    Google Scholar 

  12. Magnusdottir, A., Masson, M., Loftsson, T.: Molecular modeling of diflunisal and ibuprofen in 2-hydroxypropyl-β-cyclodextrin cavity in the gas phase. J. Incl. Phenom. Macrocycl. Chem. 44, 213–218 (2002)

    Article  CAS  Google Scholar 

  13. Zidane, S., Maiza, A., Bouleghlem, H., Herizi, W., Dahmani, S.: Investigation of cyclodextrin inclusion compounds using FT-IR, SEM and X-ray diffraction. Int. J. Chem. Eng. Appl. 7, 182–185 (2016)

    CAS  Google Scholar 

  14. Erem, M., Amelie, B., Meralo, Z., Murat, S., Dominique, D., Hincal, A.A.: Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes. Pharm. Res. 20(1), 117–125 (2003)

    Article  Google Scholar 

  15. Ficarra, R., Tommasini, S., Raneri, D., Calabro, M.L., Dibella, M.R., Rustichelli, C., Gamberini, M.C., Ficarra, P.: Study of flavonoids/β-cyclodextrins inclusion complexes by NMR, FT-IR, DSC, X-ray investigation. J. Pharm. Biomed. Anal. 29, 1005–1014 (2002)

    Article  CAS  Google Scholar 

  16. Bani-Yaseen, A.D., Moala, A.: Spectral, thermal, and molecular modeling studies on the encapsulation of selected sulfonamide drugs in β-cyclodextrin nano-cavity. Spectrochim. Acta A 131, 424–431 (2014)

    Article  CAS  Google Scholar 

  17. Jahed, V., Zarrabi, A., Bordbar, A., Hafezi, M.S.: NMR (1H, ROESY) spectroscopic and molecular modelling investigations of supramolecular complex of ββ-cyclodextrin and curcumin. Food Chem. 165, 241–246 (2014)

    Article  CAS  Google Scholar 

  18. Mangolim, C.S., Moriwaki, C., Nogueira, A.C., Sato, F., Baesso, M.L., Neto, A.M., Matioli, G.: Curcumin–β-cyclodextrin inclusion complex: stability, solubility, characterisation by FT-IR, FT-Raman, X-ray diffraction and photoacoustic spectroscopy, and food application. Food Chem. 153, 361–370 (2014)

    Article  CAS  Google Scholar 

  19. Fabricia da, R.F., Iara, B.V., Edgar, L.C.R., Maria, T.S.T., Claudio, O.A., Fernanda, P.C., Fabiane, C.A., Marília, O.F.G.: Antioxidant activity of the mangiferin inclusion complex with β-cyclodextrin. LWT Food Sci. Technol. 1–6 (2013)

  20. Sandipan, C., Soumalee, B., Ansuman, L., Soumen, B.: Inclusion of chrysin in ββ-cyclodextrin nanocavity and its effect on antioxidant potential of chrysin: a spectroscopic and molecular modeling approach. J. Mol. Struct. 977, 180–188 (2010)

    Article  Google Scholar 

  21. Lauro, M.R., Carbone, C., Auditore, R., Musumeci, T., Santagati, N.A., Aquino, R.P., Puglisi, G.: A new inclusion complex of amlodipine besylate and soluble ββ-cyclodextrin polymer: preparation, characterization and dissolution profile. J. Incl. Phenom. Macrocycl. Chem. https://doi.org/10.1007/s10847-012-0168-y (2012)

    Google Scholar 

  22. El-Kosasy, A.M., Tawakkol, Sh.M., Ayad, M.F., Sheta, A.I.: New methods for amlodipine and valsartan native spectrofluorimetric determination, with factors optimization study. Talanta. https://doi.org/10.1016/j.talanta.2015.05.012 (2015)

    Google Scholar 

  23. Jadwiga, M., Agnieszka, C., Beata, C.: Inclusion complexes of felodipine and amlodipine with methyl-β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 54, 17–21 (2006)

    Article  Google Scholar 

  24. Laura, S., Lucreţia, U., Ionut, L., Zoltan, S., Adriana, F., Claudiu, S.: β-Cyclodextrin inclusion complexes of lisinopril and zofenopril physicochemical characterization and compatibility study of lisinopril-β-cyclodextrin with lactose. J. Therm. Anal. Calorim. 123, 2377–2390 (2016)

    Article  Google Scholar 

  25. Jinxia, L., Huizhi, Z., Yanyan, Y., Shumao, S.: Study of the inclusion complex and antioxidating activity of Wogonin with β-cyclodextrin and hydroxypropyl-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 84, 115–120 (2016)

    Article  Google Scholar 

  26. Liu, M., Dong, L., Chen, A., Zheng, Y., Sun, D., Wang, X., Wang, B.: Inclusion complexes of quercetin with three ββ-cyclodextrins derivatives at physiological pH: spectroscopic study and antioxidant activity. Spectrochim. Acta A. https://doi.org/10.1016/j.saa.2013.07.008 (2013)

    Google Scholar 

  27. Agnes, K., Vesna, N., Ljubisa, N., Mihajlo, S., Milorad, C., Ljiljana, S., Dusica, I.: Inclusion complexes of amlodipine besylate and cyclodextrins. Cent. Eur. J. Chem. 8(4), 834–841 (2010)

    Google Scholar 

  28. Sambasevam, K.P., Mohamad, Sh., Sarih, N.M., Ismail, N.A.: Synthesis and characterization of the inclusion complex of β-cyclodextrin and azomethine. Int. J. Mol. Sci. 14, 3671–3682 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We acknowledge the financial support from University of Guilan and University Campus 2, University of Guilan.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Guilan, Rasht, 41335-1914, Iran

    Nina Alizadeh

  2. Department of Chemistry, Faculty of Science, University of Guilan, University Campus 2, Rasht, Iran

    Shokufeh Malakzadeh & Nina Alizadeh

Authors
  1. Shokufeh Malakzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nina Alizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nina Alizadeh.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Malakzadeh, S., Alizadeh, N. Spectroscopic study and antioxidant activity of the inclusion complexes of cyclodextrins and amlodipine besylate drug. J Incl Phenom Macrocycl Chem 90, 89–98 (2018). https://doi.org/10.1007/s10847-017-0768-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-017-0768-7

Keywords

Search

Navigation