Synthesis and evaluation of pH-sensitive glycopolymers for oral drug delivery systems

Abstract

Sucrose esters (SE) are surfactants with potential pharmaceutical applications because of their low toxicity, biocompatibility, and excellent biodegradability. Biodegradable and biocompatible copolymeric hydrogels based on glucose-6-acrylate-1, 2, 3, 4-tetraacetate (GATA) and methacrylic acid (MAA) were designed and synthesized. Because of the growing importance of sugar-based hydrogels as drug delivery systems, these new pH-responsive glucose-containing copolymeric hydrogels were investigated for oral drug delivery. The GATA monomer was synthesized and characterized. The copolymeric hydrogel was synthesized by free-radical polymerization. Azobisisobutyronitrile (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 enzyme-free simulated gastric and intestinal fluids (SGF and SIF, respectively). A model drug, olsalazine [3, 3َ -azobis (6-hydroxy benzoic acid)] (OSZ) 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 was found to be faster in SIF. The drug-release profiles indicated that amount of drug release depends on their degree of swelling and crosslinking.

Enzymatic synthesis and structural characterization of methacryloyl‐D‐fructose‐ and methacryloyl‐D‐glucose‐based monomers and poly(methacryloyl‐D‐fructose)‐based hydrogels

“…9 Table S1 (available in the Supporting information) summarizes the main results reported in the literature regarding the functionalization of glucose and fructose with polymerizable groups using both the chemical and enzymatic (lipase and protease) routes. In general, the monomer yield/carbohydrate conversion tends to be higher for enzymatic catalysis 12,[23][24][25][26][27][28][29][30][31][32][33][34][35][36] than for the chemical route, 13,[17][18][19][37][38][39][40][41][42] however, high yields in the carbohydrate functionalization can also be achieved using some chemical routes. 13,21,39,42 Moreover, Candida Antarctica lipase B (EC 3.1.1.3), commercially available in a supported form under the name Novozym ® 435, is widely used in the functionalization of carbohydrates in organic media, including the enzymatic-catalyzed carbohydrate (meth)acrylation.…”

Synthesis and Characterization of Polymer/Silica Composite for Colon-Specific Drug Delivery

“…Glucose-6-acrylate-1,2,3,4-tetraacetate (GATA) and glucose-6-acrylate (GA) were prepared by the methods described in the literature [18,19], respectively. 3-(Trimethoxysilyl) propyl methacrylate (TSPA) (99%) was purchased from Sigma-Aldrich.…”

Macroporous hydrogels based on carbohydrates monomethacrylates and dimethacrylates: singular properties from carbohydrate‐based crosslinkers

“…28,29 Applications reported in the literature for hydrogels based on carbohydrate are mainly related to drug delivery systems. 12,[30][31][32][33][34][35][36] However, they have also been used as stationary phase in high-performance liquid chromatography 37 and as cell culture media. 38 Crosslinking agents play a key role on the mechanical and physical chemical properties of the hydrogels.…”