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Synthesis and Characterization of Crosslinked Polyacrylates Containing Cubane and Silyl Groups
Mahkam Mehrdad,Assadi Mohammad,Mohammadzadeh Rana The Polymer Society of Korea 2006 Macromolecular Research Vol.14 No.1
Attaching the organosilyl groups to macromolecular chains of 2-hydroxyethyl methacrylate (HEMA) should lead to important modifications of polymer properties. t-$BuMe_{2}Si$ and cubane-l, 4-dicarboxylic acid (CDA) were covalently linked with 2-hydroxyethyl methacrylate (HEMA). The silyl-linked HEMA is abbreviated as TSMA, while cubane-l ,4-dicarboxylic acid (CDA) linked to two HEMA groups is the cross-linking agent (CA). Free radical cross-linking copolymerization of TSMA and HEMA with various ratios of CA as the cross-linking agent was carried out at 60-70$^{circ}C$. The compositions of the cross-linked, three-dimensional polymers were determined by FTIR spectroscopy. The glass transition temperature ($T_{g}$) of the network polymers was determined calorimetrically. The $T_{g}$ of the network polymer increased with increasing cross-linking degree.
Mahkam, Mehrdad,Poorgholy, Nahid,Vakhshouri, Laleh The Polymer Society of Korea 2009 Macromolecular Research Vol.17 No.9
The aim of this study was to develop novel intestinal specific drug delivery systems with pH sensitive swelling and drug release properties. The carboxyl group of ibuprofen was converted to a vinyl ester group by reacting ibuprofen and vinyl acetate as an acylating agent in the presence of catalyst. The glucose-6-acrylate-1, 2, 3, 4-tetraacetate (GATA) monomer was prepared under mild conditions. Cubane-1, 4-dicarboxylic acid (CDA) linked to two 2-hydroxyethyl methacrylate (HEMA) group was used as the crosslinking agent (CA). Methacrylic-type polymeric prodrugs were synthesized by the free radical copolymerization of methacrylic acid, vinyl ester derivative of ibuprofen (VIP) and GATA in the presence of cubane cross linking agent. The structure of VIP was characterized and confirmed by FTIR, $^1H$ NMR and $^{13}C$ NMR spectroscopy. The composition of the cross-linked three-dimensional polymers was determined by FTIR spectroscopy. The hydrolysis of drug polymer conjugates was carried out in cel-lophane membrane dialysis bags, and the in vitro release profiles were established separately in enzyme-free simulated gastric and intestinal fluids (SGF, pH 1 and SIF, pH 7.4). The detection of a hydrolysis solution by UV spectroscopy at selected intervals showed that the drug can be released by hydrolysis of the ester bond between the drug and polymer backbone at a low rate. Drug release studies showed that increasing the MAA content in the copolymer enhances the rate of hydrolysis in SIP. These results suggest that these polymeric prodrugs can be useful for the release of ibuprofen in controlled release systems.