Application of 2-hydroxyethyl methacrylate polymers in controlled release of 5-aminosalicylic acid as a colon-specific drug |
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Authors: | Mirzaagha Babazadeh Ladan Edjlali Lida Rashidian |
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Affiliation: | (1) Laboratory of Organic Chemistry Research, Department of Applied Chemistry, Islamic Azad University, Tabriz Branch, P.O. Box 1655, Tabriz, Iran |
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Abstract: | Acrylic type polymeric systems having degradable ester bonds linked to 5-aminosalicylic acid were synthesized and evaluated
as materials for drug delivery. 5-Aminosalicylic acid, as an important drug in the treatment of inflammatory bowel diseases,
was linked to 2-hydroxyethyl methacrylate by activated ester methodology in two-step and one-pot procedures to obtain methacryloyloxyethyl
5-amino salicylate. The resulting methacrylic derivative of 5-aminosalicylic acid was copolymerized with methacrylamide, 2-hydroxyethyl
methacrylate and methyl methacrylate (in 1:3 mole ratio) by free radical polymerization method in N,N-dimethylformamide solution, utilizing α,ά-azoisobutyronitrile as initiator at the temperature range of 65–70 °C. The obtained
polymers were characterized by FT-IR, 1H NMR, 13C NMR and elemental analysis. The average molecular weights of the polymers bearing drug units as side substituents of the
acrylic backbone were determined by gel permeation chromatography and their polydispersity indices resulted in the range of
1.6–1.8. Release studies of 5-aminosalicylic acid were performed into dialysis bags by hydrolysis in buffered solutions (pH
1, 7 and 8) at 37 °C. 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 drug moiety. The release profiles indicated that the hydrolytic behavior
of polymeric prodrugs is strongly based on the polymer hydrophilicity and the pH value of the hydrolysis solution. The results
suggest that these systems could be useful for preparation of a controlled release formulation of 5-aminosalicylic acid in
colon. |
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Keywords: | 5-aminosalicylic acid controlled release 2-hydroxyethyl methacrylate methacrylic polymers pH-sensitive polymers polymeric prodrugs |
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