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Investigation of the Interactions in Complexes of Low Molecular Weight Chitosan with Ibuprofen

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Abstract

Complexation between ibuprofen and low molecular weight chitosan (LMWC) was studied. LMWC was prepared from high molecular weight chitosan using the acid hydrolysis method. The complexes were investigated by using DSC, FT-IR and liquid-state 1H-NMR. Molecular mechanics (MM) calculations were used to give insight into the stoichiometry of the interaction of chitosan with ibuprofen. The results showed that complexation of ibuprofen with LMWC involves ionic interaction between the ammonium group of LMWC and the carboxylate anion of ibuprofen. It was also shown that it is more efficient to prepare the complexes using lower concentration solutions of the polymer. These results were supported by molecular mechanics calculations. The experimental results may explain the discrepancies in the literature where, in many studies, the concentration of chitosan and its low average molecular weight were not considered to be important factors in the complexation process.

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Authors and Affiliations

  1. Department of Medicinal Chemistry and Pharmacognosy, Faculty of Pharmacy, Jordan University of Science and Technology, P.O. Box 3030, Irbid, 22110, Jordan

    Amjad M. Qandil

  2. Department of Pharmaceutical Technology, Faculty of Pharmacy, Jordan University of Science and Technology, P.O. Box 3030, Irbid, 22110, Jordan

    Aiman A. Obaidat, Muaadh A. Mohammed Ali, Bashar M. Al-Taani & Bassam M. Tashtoush

  3. Jordanian Pharmaceutical Manufacturing Company, P.O. Box 94, Naor, 1170, Jordan

    Nawzat D. Al-Jbour, Mayyas M. Al Remawi, Khaldoun A. Al-Sou’od & Adnan A. Badwan

  4. Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O. Box 130040, Mafraq, 25113, Jordan

    Khaldoun A. Al-Sou’od

Authors
  1. Amjad M. Qandil
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  2. Aiman A. Obaidat
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  3. Muaadh A. Mohammed Ali
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  4. Bashar M. Al-Taani
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  5. Bassam M. Tashtoush
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  6. Nawzat D. Al-Jbour
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  7. Mayyas M. Al Remawi
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  8. Khaldoun A. Al-Sou’od
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  9. Adnan A. Badwan
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Correspondence to Amjad M. Qandil.

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Qandil, A.M., Obaidat, A.A., Ali, M.A.M. et al. Investigation of the Interactions in Complexes of Low Molecular Weight Chitosan with Ibuprofen. J Solution Chem 38, 695–712 (2009). https://doi.org/10.1007/s10953-009-9405-4

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  • DOI: https://doi.org/10.1007/s10953-009-9405-4

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