Synthesis and Anticoagulant Activity of Polyureas Containing Sulfated Carbohydrates

Abstract

Polyurea-based synthetic glycopolymers containing sulfated glucose, mannose, glucosamine, or lactose as pendant groups have been synthesized by step-growth polymerization of hexamethylene diisocyanate and corresponding secondary diamines. The obtained polymers were characterized by gel permeation chromatography, nuclear magnetic resonance spectroscopy, and Fourier transform infrared spectroscopy. The nonsulfated polymers showed similar results to the commercially available biomaterial polyurethane TECOFLEX in a platelet adhesion assay. The average degree of sulfation after reaction with SO3 was calculated from elemental analysis and found to be between three and four −OSO3 groups per saccharide. The blood-compatibility of the synthetic polymers was measured using activated partial thromboplastin time, prothrombin time, thrombin time, anti-IIa, and anti-Xa assays. Activated partial thromboplastin time, prothrombin time, and thrombin time results indicated that the mannose and lactose based polymers had the highest anticoagulant activities among all the sulfated polymers. The mechanism of action of the polymers appears to be mediated via an anti-IIa pathway rather than an anti-Xa pathway.

Hydrogel‐coated polyurethane/urea shape memory polymer foams

“…Thrombosis at the biomaterial surface has been recognized as one of the primary causes of blood‐contacting device failure . In our previous work, linear polyureas with sulfated sugars showed effective anticoagulant properties by prolonging blood clotting in solution. Subsequently, these sugar‐functionalized polyureas and poly(ethylene glycol) were covalently cross‐linked and prepared as SMP films and foams .…”

Lactose‐containing hydrogels for enzyme stabilization

“…38 Lactose was acetylated to protect the hydroxyl groups and the anomeric acetate group selectively deprotected by benzyl amine (L03). After activating the anomeric hydroxyl group with trichloroacetonitrile, a glycosylation reaction was performed by adding N-hydroxyethyl acrylamide with boron trifluoride diethyl etherate to generate the acetyl-protected lactose-acrylamide (L05).…”

“…This strategy is based on literature showing lactose solutions stabilizing proteins such as ribonuclease A, chymotrypsinogen A, bovine serum albumin, and ovalbumin. 36 Lactose-containing polymers/hydrogels are potentially biocompatible, biodegradable, and biorenewable materials, with applications including as anticoagulants, 37,38 water adsorbents, [39][40][41] sensors. 42,43 We synthesized a lactosecontaining monomer, N-(2-lactosylethyl)acrylamide and copolymerized it with N-hydroxyethyl acrylamide (HEAA) to produce a set of hydrogels with different monomer ratios.…”

Synthesis and characterization of lactose grafted polycaprolactone‐polysiloxane‐polycaprolactone copolymers

“…for tissue engineering scaffolds and drug delivery carriers . However, when a non‐native biomaterial comes into contact with blood, a cascade reaction may be initiated, resulting in protein adsorption on the non‐native biomaterial, platelet adhesion and activation, and clot formation . Then, to improve its blood compatibility, the incorporation of bioactive molecules or hydrophilic groups into the aliphatic polyester is a primary concern.…”