Babazadeh Mirzaagha, Sheidaei Maryam, Abbaspour Sara, Edjlali Ladan
Department of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, Tabriz, Iran.
Sci Pharm. 2013 Jan-Mar;81(1):281-96. doi: 10.3797/scipharm.1204-14. Epub 2012 Dec 10.
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, (1)H NMR, (13)C 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.
本研究工作描述了具有与布洛芬相连的可降解酯键的新型丙烯酸类聚合物体系的合成与评价，该体系作为药物递送材料。布洛芬通过活化酯法在一锅法中与甲基丙烯酸2-羟丙酯相连，产率很高。所得材料通过自由基聚合法与甲基丙烯酸2-羟乙酯或甲基丙烯酸甲酯（摩尔比为1:3）共聚，在65 - 70°C下使用偶氮异丁腈。通过傅里叶变换红外光谱（FTIR）、氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）、差示扫描量热法（DSC）和元素分析对所得产物进行表征，成功证实了它们的合成。将所得聚合物在不同缓冲溶液（pH 1、7.4和10）中放入透析袋中初步评估布洛芬的释放情况，以显示前药在水解条件下释放药物的能力。在选定的时间间隔通过紫外光谱检测水解情况，结果表明药物可以通过药物部分一侧酯键的选择性水解而释放。释放曲线表明聚合物的水解行为强烈依赖于聚合物的亲水性和水解溶液的pH值。结果表明这些聚合物可用于控释系统。
