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Sci. Pharm. 2013, 81(1), 281-296; doi:10.3797/scipharm.1204-14

Synthesis, Characterization, and In Vitro Evaluation of New Ibuprofen Polymeric Prodrugs Based on 2-Hydroxypropyl Methacrylate

Department of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, Tabriz, Iran
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Author to whom correspondence should be addressed.
Received: 16 April 2012 / Accepted: 10 December 2012 / Published: 10 December 2012
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Abstract

The present research work describes the synthesis and evaluation of new acrylic-type polymeric systems having degradable ester bonds linked to ibuprofen as materials for drug delivery. Ibuprofen was linked to 2-hydroxy-propyl methacrylate by an activated ester methodology in a one-pot procedure with a high yield. The resulting material was copolymerized with either 2-hydroxyethyl methacrylate or methyl methacrylate (in 1:3 mole ratios) by the free radical polymerization method, utilizing azoisobutyronitrile at 65–70 °C. The characterization of the resulting products by FTIR, 1H NMR, 13C NMR, DSC, and elemental analysis confirmed their synthesis successfully. Ibuprofen release from the obtained polymers was preliminarily evaluated at different buffered solutions (pH 1, 7.4, and 10) into dialysis bags to show the capacity of prodrugs to release the drug under hydrolytic conditions. Detection of hydrolysis by UV spectroscopy at selected intervals showed that the drug can be released by selective hydrolysis of the ester bond at the side of the drug moiety. The release profiles indicated that the hydrolytic behavior of polymers is strongly based on the polymer hydrophilicity and the pH value of the hydrolysis solution. The results suggest that these polymers could be useful in controlled release systems.
Keywords: Ibuprofen; 2-Hydroxypropyl methacrylate; Polymeric prodrugs; Controlled release systems; Polymerization Ibuprofen; 2-Hydroxypropyl methacrylate; Polymeric prodrugs; Controlled release systems; Polymerization
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

BABAZADEH, M.; SHEIDAEI, M.; ABBASPOUR, S.; EDJLALI, L. Synthesis, Characterization, and In Vitro Evaluation of New Ibuprofen Polymeric Prodrugs Based on 2-Hydroxypropyl Methacrylate. Sci. Pharm. 2013, 81, 281-296.

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