Publication Type Journal Article
Title Elucidating the guest-host interactions and complex formation of praziquantel and cyclodextrin derivatives by C-13 and N-15 solid-state NMR spectroscopy
Authors Eva C. Arrua M J Ferreira Claudio J. Salomon Teresa G. Nunes
Groups BioMol
Journal INTERNATIONAL JOURNAL OF PHARMACEUTICS
Year 2015
Month December
Volume 496
Number 2
Pages 812-821
Abstract Praziquantel is the drug of choice to treat several parasitic infections including the neglected tropical disease schistosomiasis. Due to its low aqueous solubility, cyclodextrins have been tested as potential host candidates to prepare praziquantel inclusion complexes with improved solubility. For the first time, the interactions of praziquantel with beta-cyclodextrin and beta-cyclodextrin derivatives (methyl-beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin) were investigated using high resolution solid-state NMR spectroscopy. The results of this work confirmed that solid-state NMR experiments provided structural characterization, demonstrating the formation of inclusion complexes most probably with PZQ adopting an anti conformation, also the most likely in amorphous raw PZQ. Further information on the interaction of praziquantel with methyl-beta-cyclodextrin was obtained from proton rotating-frame relaxation time measurements, sensitive to kilohertz-regime motions but modulated by spin-diffusion. Evidences were presented in all cases for praziquantel complexation through the aromatic ring. In addition, 1:2 drug: carrier molar ratio appears to be the most probable and therefore suitable stoichiometry to improve pharmaceutical formulations of this antischistosomal drug. (C) 2015 Elsevier B.V. All rights reserved.
DOI http://dx.doi.org/10.1016/j.ijpharm.2015.11.026
ISBN
Publisher ELSEVIER SCIENCE BV
Book Title
ISSN 0378-5173
EISSN 1873-3476
Conference Name
Bibtex ID ISI:000367384700067
Observations
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