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

Abstract

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.

Development and characterization of pH‐responsive polyethylene glycol‐co‐poly(methacrylic acid) polymeric network system for colon target delivery of oxaliplatin: Its acute oral toxicity study

“…[14] The pH in stomach (<3) is lower as compare to intestinal pH (>6) and this pH difference is sufficient to elicit pH-dependent behavior of hydrogels. [14] The pH in stomach (<3) is lower as compare to intestinal pH (>6) and this pH difference is sufficient to elicit pH-dependent behavior of hydrogels.…”

“…BARBAT ATtBal environmental pH (e.g., in gastrointestinal tract), are very useful for colon targeting drug delivery systems. [14] The pH in stomach (<3) is lower as compare to intestinal pH (>6) and this pH difference is sufficient to elicit pH-dependent behavior of hydrogels. [15] At lower pH, hydrogels remain collapsed and drug molecules remain protected from the acidic environment of stomach due to limited release of drug.…”

Preparation and characterization of water-soluble microcapsule for sustained drug release using Eudragit RS 100

“…[1][2][3][4][5] A controlled release of therapeutic agents is very important in the area of DDS and has been extensively studied. 6,7 The advantages of controlled release include greater drug efficiency, better balanced drug concentrations in the body, and more convenience to the patient. [8][9][10] To achieve the goal of controlled release, a proper delivery system is in various shapes using tablets, pellets, spheres and capsules.…”

Biodegradable pH- and temperature-sensitive multiblock copolymer hydrogels based on poly(amino-ester urethane)s

“…1,2 Hydrogels based on natural polymers 3,4 and synthetic polymers 5,6 have been developed for biomedical applications. In the past decade, stimuli-responsive polymers and hydrogels that respond to changes in external stimuli such as the temperature, ionic strength, pH, electric field and magnetic field [7][8][9][10][11][12][13][14][15][16][17][18] have been extensively investigated. Among them, in situ gelling stimuli-sensitive hydrogels have attracted considerable interest due to their unique advantages in drug delivery applications.…”