Drug Delivery and Translational Research

, Volume 9, Issue 1, pp 273–283 | Cite as

Synthesis and characterization of a new cyclodextrin derivative with improved properties to design oral dosage forms

  • Agustina García
  • Josefina Priotti
  • Ana Victoria Codina
  • María Delia Vasconi
  • Ariel D. Quiroga
  • Lucila I. Hinrichsen
  • Dario LeonardiEmail author
  • María Celina LamasEmail author
Original Article


This work aimed to synthesize a novel β-cyclodextrin derivative, itaconyl-β-cyclodextrin to evaluate whether albendazole inclusion complexes with the new β-cyclodextrin derivative-improved albendazole dissolution efficiency and its anthelminthic activity. The new derivative was thoroughly evaluated and characterized, and an average degree of substitution of 1.4 per cyclodextrin molecule was observed. Albendazole:itaconyl-β-cyclodextrin complexes were prepared by spray drying procedures and investigated using phase solubility diagrams, dissolution efficiency, X-ray diffraction, differential scanning calorimetry, Fourier transform infrared, scanning electronic microscopy, mass spectrometry, and nuclear magnetic resonance spectroscopy. Phase solubility diagrams and mass spectrometry studies showed that the inclusion complex was formed in an equimolar ratio. Stability constant values were 602 M−1 in water, and 149 M−1 in HCl 0.1 N. Nuclear magnetic resonance experiments of the inclusion complex showed correlation signals between the aromatic and propyl protons of albendazole and the itaconyl-β-cyclodextrin inner protons. The studies indicated solid structure changes of albendazole included in itaconyl-β-cyclodextrin. The maximum drug release was reached at 15 min, and the inclusion complex solubility was 88-fold higher than that of the pure drug. The in vitro anthelmintic activity assay showed that the complex was significantly more effective than pure albendazole.


Cyclodextrins Synthesis Poorly water-soluble drug Albendazole Physicochemical characterization 



J.P. and A.G. are grateful to CONICET (Consejo Nacional de Investigaciones Científicas y Técnicas) for a Doctoral and a Posdoctoral Fellowship.

Funding information

This work was supported by the Universidad Nacional de Rosario, CONICET (Project No. PIP 112-201001-00194) and Agencia Nacional de Promoción Científica y Tecnológica (Project No. PICT 2006-1126).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Animal studies

All institutional and national guidelines for the care and use of laboratory animals were followed.


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Copyright information

© Controlled Release Society 2018

Authors and Affiliations

  1. 1.IQUIR-CONICETRosarioArgentina
  2. 2.Departamento de Farmacia, Facultad de Ciencias Bioquímicas y FarmacéuticasUniversidad Nacional de RosarioRosarioArgentina
  3. 3.Instituto de Genética Experimental, Facultad de Ciencias MédicasUniversidad Nacional de RosarioRosarioArgentina
  4. 4.CIC-UNRUniversidad Nacional de RosarioRosarioArgentina
  5. 5.Área Parasitología, Facultad de Ciencias Bioquímicas y FarmacéuticasUniversidad Nacional de RosarioRosarioArgentina
  6. 6.Instituto de Fisiología Experimental (IFISE-CONICET)RosarioArgentina
  7. 7.Facultad de Ciencias Bioquímicas y FarmacéuticasUniversidad Nacional de RosarioRosarioArgentina

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