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Novel inclusion complex of ibuprofen tromethamine with cyclodextrins: Physico-chemical characterization

Novel inclusion complex of ibuprofen tromethamine with cyclodextrins: Physico-chemical characterization

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Al Omari, Mahmoud M., Daraghmeh, Nidal H., El-Barghouthi, Musa I., Zughul, Mohammad B., Chowdhry, Babur Z., Leharne, Stephen A. and Badwan, Adnan A. (2009) Novel inclusion complex of ibuprofen tromethamine with cyclodextrins: Physico-chemical characterization. Journal of Pharmaceutical and Biomedical Analysis, 50 (3). pp. 449-458. ISSN 0731-7085 (doi:10.1016/j.jpba.2009.05.031)

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Abstract

Guest-host interactions of ibuprofen tromethamine salt (Ibu.T) with native and modified cyclodextrins (CyDs) have been investigated using several techniques, namely phase solubility diagrams (PSDs), proton nuclear magnetic resonance (H-1 NMR), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffractometry (XRPD). scanning-electron microscopy (SEM) and molecular mechanics (MM). From the analysis of PSD data (A(L)-type) it is concluded that the anionic tromethamine salt of ibuprofen (pK(a) = 4.55) forms 1: 1 soluble complexes with all CyDs investigated in buffered water at pH 7.0, while the neutral form of Ibu forms an insoluble complex with beta-CyD (B-S-type) in buffered water at pH 2.0. Ibu.T has a lower tendency to complex with beta-CyD (K-11 = 58 M-1 at pH 7.0) compared with the neutral Ibu (K-11 = 4200 M (1)) in water. Complex formation of Ibu.T with beta-CyD (Delta G degrees = -20.4 kJ/mol) is enthalpy driven (Delta H degrees = -22.9 kJ/mol) and is accompanied by a small unfavorable entropy (Delta S degrees = -8.4 J/mol K) change. H-1 NMR studies and MM computations revealed that, on complexation, the hydrophobic central benzene ring of lbu.T and part of the isobutyl group reside within the beta-CyD cavity leaving the peripheral groups (carboxylate, tromethamine and methyl groups) located near the hydroxyl group networks at either rim of beta-CyD. PSD, H-1 NMR, DSC, FT-IR, XRPD, SEM and MM studies confirmed the formation of Ibu.T/beta-CyD inclusion complex in solution and the solid state. (C) 2009 Elsevier B.V. All rights reserved.

Item Type: Article
Additional Information: [1] First available online: 23 June 2009. [2] First published in print: 15 October 2009. [3] Published as: Journal of Pharmaceutical and Biomedical Analysis, (2009), Volume 50, Issue 3, pp. 449–458.
Uncontrolled Keywords: ibuprofen, tromethamine, cyclodextrin, phase solubility, complex characterization
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
Faculty / Department / Research Group: Faculty of Engineering & Science > Department of Life & Sports Sciences
Faculty of Engineering & Science > Department of Pharmaceutical, Chemical & Environmental Sciences
Related URLs:
Last Modified: 05 Dec 2016 14:08
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/1594

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