Complexation of sodium picosulphate with beta cyclodextrin: NMR spectroscopic study in solution

  • Arti MaheshwariEmail author
  • Manisha Sharma
  • Deepak Sharma
Original Article


Sodium Picosulphate (SPL) is a synthetic drug, widely used for thorough evacuation of the bowel, usually for patients who are preparing to undergo a colonoscopy. Cyclodextrins (CDs) are chiral, truncated cone shaped, cyclic oligosaccharides that can encapsulate a variety of drug molecules into inclusion complexes, thereby increasing their stability and solubility. 1H NMR spectroscopic studies showed the inclusion complexation between β-CD and SPL, based on the upfield shift changes in the β-CD cavity protons (H-3′ and H-5′) and downfield shift changes in the guest (SPL) protons. The structure of inclusion complexes was determined by 2D ROESY spectral data. The 1:1 stoichiometry and overall association constant (Ka) were determined by using Scott’s plot method to be 450 M−1.


Sodium picosulphate β-Cyclodextrin ROESY COSY NMR Inclusion complex 


  1. 1.
    Kienzle-Horn, S., Vix, J.M., Schuijt, C., Peil, H., Jordan, C.C., Kamm, M.A.: Comparison of bisacodyl and sodium picosulphate in the treatment of chronic constipation. Curr. Med. Res. Opin. 23, 691–699 (2007)CrossRefGoogle Scholar
  2. 2.
    Hoy, S.M., Scott, L.J., Wagstaff, A.J.: Sodium picosulfate/magnesium citrate: a review of its use as a colorectal cleanser. Drugs 69, 123–136 (2009)CrossRefGoogle Scholar
  3. 3.
    Liu, Y., You, C.-C., Zhang, H.Y., Zhao, Y.L.: Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side. Eur. J. Org. Chem. 8, 1415–1422 (2003)CrossRefGoogle Scholar
  4. 4.
    Pandit, V., Gorantla, R., Devi, K., Pai, R.S., Sarasija, S.: Preparation and characterization of pioglitazone cyclodextrin inclusion complexes. J. Young Pharm. 3, 267–274 (2011)CrossRefGoogle Scholar
  5. 5.
    Putterman, W., Caers, J., Masens, J., Peters, J.: Abstract International Conference of Pharmaceutical Applications of Cyclodextrin Conference, Lawrence (1997)Google Scholar
  6. 6.
    Mielcarek, J., Czernielewska, A., Czarczynska, B.: Inclusion complexes of felodipine and amlodipine with methyl-β-cyclodextrin. J. Incl. Phenom. Mol. Recogn. 54, 17 (2006)CrossRefGoogle Scholar
  7. 7.
    Torres-Labandeira, J.J., Blanco-Mendez, J., Vila-jato, J.L.: Biopharmaceutical stability of the glibornuride/bet-cyclodextrin inclsuion complex after one year of storage. S. T. P. Pharm. Sci. 4, 235 (1994)Google Scholar
  8. 8.
    Thompson, D.O.: Cyclodextrins as enabling excipients: their present and future use in pharmaceuticals. CRC Crit. Rev. Ther. Drug. Carrier Syst. 14, 1 (1997)Google Scholar
  9. 9.
    Fromming, K.H., Szejtli, J.: Cyclodextrins in Pharmacy. Kluwer, Dordrecht (1994)CrossRefGoogle Scholar
  10. 10.
    Fermeglia, M., Ferrone, M., Lodi, A., Pricl, S.: Host–guest inclusion complexes between anticancer drugs and β-cyclodextrin: computational studies. Carbohydr. Polym. 53, 15–44 (2003)CrossRefGoogle Scholar
  11. 11.
    Brun, H., Paul, M., Razzouq, N., Binhas, M., Gibaud, S., Astier, A.: Cyclodextrin inclusion complexes of the central analgesic drug nefopam. Drug Dev. Ind. Pharm. 32, 1123–1134 (2006)CrossRefGoogle Scholar
  12. 12.
    Tiwari, G., Tiwari, R., Rai, A.K.: Cyclodextrins in delivery systems: applications. J. Pharm. Bioallied Sci. 2, 72–79 (2010)CrossRefGoogle Scholar
  13. 13.
    Jones, R.A.Y.: Physical and Mechanistic Organic Chemistry, pp. 227–235. Cambridge University Press, London (1979)Google Scholar
  14. 14.
    Helm, H., Muller, B.W., Waaler, T.: Complexation of dihydroergotamine mesylate with cyclodextrin derivatives: solubility and stability in aqueous solution. Eur. J. Pharm. Sci. 3, 195–201 (1995)CrossRefGoogle Scholar
  15. 15.
    Schneider, H.-J., Hacket, F., Rudiger, V., Ikeda, H.: NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98, 1755–1786 (1998) and references cited thereinGoogle Scholar
  16. 16.
    Dodziuk, H.: Cyclodextrins and their complexes chemistry, analytical methods, applications. Wiley, London (2006)CrossRefGoogle Scholar
  17. 17.
    Maheshwari, A., Sharma, M., Sharma, D.: Investigation of the binding of roxatidine acetate hydrochloride with cyclomaltoheptaose (β-cyclodextrin) using IR and NMR spectroscopy. Carbohydr. Res. 346, 1809–1813 (2011)CrossRefGoogle Scholar
  18. 18.
    Maheshwari, A., Sharma, D.: A comparative study of inclusion complexes of flunarizine with alpha (α-CD) and beta-cyclodextrin (β–CD). J. Incl. Phenom. Macro. Chem. 68, 453–459 (2010)CrossRefGoogle Scholar
  19. 19.
    Ali, S.M., Maheshwari, A.: 1H NMR spectroscopic study of complexation of citalopram with β-cyclodextrin in aqueous solution. Mag. Res. Chem. 45, 253–256 (2007)CrossRefGoogle Scholar
  20. 20.
    Scott, R.L.: Some comments on the Benesi-Hildebrand equation. Recl. Trav. Chim. Pays-Bas 75, 787–789 (1956)CrossRefGoogle Scholar
  21. 21.
    Kahle, C., Holzgrabe, U.: Determination of binding constants of cyclodextrin inclusion complexes with amino acids and dipeptides by potentiometric titration. Chirality 16, 509–515 (2004)CrossRefGoogle Scholar
  22. 22.
    Acosta, G., Linares, D., Olsina, R., Martínez, L.D., Gomez, M.R.: Determination of the binding constant of indomethacin-beta-cyclodextrin complex by capillary electrophoresis: experimental optimization and temperature study. Pharmazie 62, 847–852 (2007)Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  • Arti Maheshwari
    • 1
    Email author
  • Manisha Sharma
    • 1
  • Deepak Sharma
    • 2
  1. 1.Department of ChemistryMangalayatan UniversityAligarhIndia
  2. 2.Department of PhysicsMangalayatan UniversityAligarhIndia

Personalised recommendations