d-Glucose based bisacrylamide crosslinker: synthesis and study of homogeneous biocompatible glycopolymeric hydrogels

Abstract

The ability of sugar pendants in glycopolymers to mimic that on the cell surface can be used as a reliable method for the site specific delivery of drugs. In the search for new possibilities, we herein report a Dglucose based synthesis of hitherto unknown bisacrylamide crosslinker (Glc-bis), a related acrylamide monomer (Glc-acryl), with hemiacetal functionality. A one pot process to transform the synthesized Glcacrylamides to sterilized homogeneous glycopolymeric gel (Glc-gel) was investigated using radiation induced polymerization technique. The Glc-gel was subjected to swelling studies, viscoelastic, and thermal analysis. The in vitro cytotoxicity test revealed that the constituents (Glc-acryl and Glc-bis) as well as the Glc-gel were non toxic to the cells and the cells grew normally in their presence. The synthesized Glc-gel was found to show good affinity to lectin Con A demonstrating that replacing hydroxyl group in D-glucose moiety with amide bond does not largely affect its interaction with lectins.

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

“…The increase of the crosslinking density leads to a decrease of the degrees of freedom of the polymer chain and the water swelling capability and kinetics, thereby decreasing the swelling rate. This dependence of the swelling rate on crosslinking density has been reported in the literature …”

“…(B). As expected, the water swelling coefficient decreases with increasing crosslinking density . The water in the PFMA hydrogels is mostly freezable water (free water and freezable bound water).…”

“…Carbohydrate (meth)acrylate‐based polymers combine an apolar backbone with polar carbohydrate moieties, which endow polymers with water solubility without backbone degradation . These polymers can also present unique characteristics associated with the carbohydrates in their structure, such as biodegradability, biocompatibility and also specific biological interactions . These exceptional characteristics make glycopolymers of significant interest for biological and biomedical applications, such as synthetic skin, drug delivery systems, cellular surface mimics and cellular culture matrices, and also for different applications, such as, surfactants, membranes, supports for chromatography columns and polyelectrolytes, for example …”

“…Moreover, carbohydrate moieties in the polymers present the capability of specific interactions with proteins. For example, glucose moieties interact with lectins, glycoproteins responsible for specific interactions with carbohydrates in the cell membrane, and, fructose moieties interact with GLUT5 receptors, a fructose receptor in cell membranes overexpressed in breast cancer cells and tissues, but not in healthy mammary tissues …”

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

“…The carbohydrate moieties in glycopolymers are capable of playing some specific biological interactions, such as interactions between glucose moieties with the lectin Concanavalin A and interactions between fructose moieties with the glucose receptor GLUT5 (receptor overexpressed in the cell membrane of mammalian cancer cells) . Moreover, hydrophilic polymers such as polysaccharides and glycopolymers present anti‐fouling properties that diminish protein and bacterial adhesion, avoiding platelet adhesion, inflammation, device failure, blood clots, and so on .…”