Regulation of Controlled Release of Ibuprofen from Crosslinked Polymers Containing Cubane as a New Crosslinking Agent

Mahkam, Mehrdad; Sanjani, Nasser Sharifi; Entezami, Ali Akbar

doi:10.1106/m3wa-3mew-xyyn-v3j4

Cited by 32 publications

(20 citation statements)

References 4 publications

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“…Cubane-1,4-bis(methacryloyloxyethyl)carboxylate (CA) and glucose-6-acrylate-1,2,3,4-tetraacetate (GATA) were prepared by the methods described in the literatures, 25,26 respectively. Ibuprofen was purchased from Aldrich chemical company.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and characterization of novel ph-sensitive hydrogels containing ibuprofen pendents for colon-specific drug delivery

2009

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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 crosslinking agent. The structure of VIP was characterized and confirmed by FTIR, 1 H NMR and 1 3 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 cellophane 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 SIF. These results suggest that these polymeric prodrugs can be useful for the release of ibuprofen in controlled release systems.

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Section: Methodsmentioning

confidence: 99%

Synthesis and characterization of novel ph-sensitive hydrogels containing ibuprofen pendents for colon-specific drug delivery

2009

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“…Cubane-1,4-bis(methacryloyloxyethyl) carboxylate (CA) was prepared by the method described in the literature. 20 The solvents and reagents were purchased from Merck and Fluka Co. THF was dried by standard method and t-BuMe 2 SiCl used as received. Initiator of, α,α'-azobis (isobutyronitrile) (AIBN) was purified by crystallization from methanol.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and characterization of crosslinked polyacrylates containing cubane and silyl groups

2006

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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-1,4-dicarboxylic acid (CDA) were covalently linked with 2-hydroxyethyl methacrylate (HEMA). The silyl-linked HEMA is abbreviated as TSMA, while cubane-1,4-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 o 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.

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“…The higher Tg values probably related to the introduction of crosslinks, which would decrease the flexibility of the chains and the ability of the chains to undergo segmental motion, which would increase the Tg values. 18 On the other hand the introduction of a strongly polar carboxylic acid group can increase the Tg value because of the formation of internal hydrogen bonds between the polymer chains.…”

Section: Thermal Behaviormentioning

confidence: 99%

Synthesis and Evaluation of Biocompatible pH-Sensitive Hydrogels as Colon-Specific Drug Delivery Systems

Mahkam

Mohammadi

Siadat

2006

Jnl Chinese Chemical Soc

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Because of the growing importance of pH-sensitive hydrogels as drug delivery systems, biocompatible copolymeric hydrogels based N-vinyl-2-pyrrolidinone (NVP) and methacrylic acid (MAA) were designed and synthesized. These hydrogels were investigated for oral drug delivery. Radical copolymerizations of N-vinyl-2-pyrrolidinone (NVP) and methacrylic acid (MAA) with the various ratios of crosslinking agent were carried out at 70°C. Azabisisobutyronitrile (AIBN) was the free-radical initiator employed and Cubane-1,4-dicarboxylic acid (CDA) linked to two 2-hydroxyethyl methacrylate (HEMA) group was the crosslinking agent (CA) used for hydrogel preparations. The hydrogels were characterized by differential scanning calorimetry and FT-IR. Equilibrium swelling studies were carried out in enzymefree simulated gastric and intestinal fluids (SGF and SIF, respectively). A model drug, olsalazine [3,3¢-azobis (6-hydroxy benzoic acid)] (OSZ) as an azo derivative of 5-aminosalicylic acid (5-ASA), was entrapped in these gels and the in-vitro release profiles were established separately in both enzyme-free SGF and SIF. The drug-release profiles indicated that the amount of drug released depended on the degree of swelling. The swelling was modulated by the amount of crosslinking of the polymer bonded drug (PBDs) prepared. Based on the great difference in hydrolysis rates at pH 1 and 7.4, these pH-sensitive hydrogels appear to be good candidates for colon-specific drug delivery.

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Regulation of Controlled Release of Ibuprofen from Crosslinked Polymers Containing Cubane as a New Crosslinking Agent

Cited by 32 publications

References 4 publications

Synthesis and characterization of novel ph-sensitive hydrogels containing ibuprofen pendents for colon-specific drug delivery

Synthesis and characterization of novel ph-sensitive hydrogels containing ibuprofen pendents for colon-specific drug delivery

Synthesis and characterization of crosslinked polyacrylates containing cubane and silyl groups

Synthesis and Evaluation of Biocompatible pH-Sensitive Hydrogels as Colon-Specific Drug Delivery Systems

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