Design of Xylose-Based Semisynthetic Polyurethane Tissue Adhesives with Enhanced Bioactivity Properties

Abstract

Developing biocompatible tissue adhesives with high adhesion properties is a highly desired goal of the tissue engineering due to adverse effects of the sutures. Therefore, our work involves synthesis, characterization, adhesion properties, protein adsorption, in vitro biodegradation, in vitro and in vivo biocompatibility properties of xylose-based semisynthetic polyurethane (NPU-PEG-X) bioadhesives. Xylose-based semisynthetic polyurethanes were developed by the reaction among 4,4'-methylenebis(cyclohexyl isocyanate) (MCI), xylose and polyethylene glycol 200 (PEG). Synthesized polyurethanes (PUs) showed good thermal stability and high adhesion strength. The highest values in adhesion strength were measured as 415.0 ± 48.8 and 94.0 ± 2.8 kPa for aluminum substrate and muscle tissue in 15% xylose containing PUs (NPU-PEG-X-15%), respectively. The biodegradation of NPU-PEG-X-15% was also determined as 19.96 ± 1.04% after 8 weeks of incubation. Relative cell viability of xylose containing PU was above 86%. Moreover, 10% xylose containing NPU-PEG-X (NPU-PEG-X-10%) sample has favorable tissue response, and inflammatory reaction between 1 and 6 weeks implantation period. With high adhesiveness and biocompatibility properties, NPU-PEG-X can be used in the medical field as supporting materials for preventing the fluid leakage after abdominal surgery or wound closure.

Bio‐Based Polyurethanes from Carbohydrate Monomers

“…Tertiary amines can also accelerate the polymerization process, and among them, the most extensively selected catalysts are 1,4-diazabicyclo[2.2.2]octane (DABCO) [10] and N,N-dimethylcyclohexylamine (DMCHA) [33]. Triethylamine (TEA) was chosen as (co-)catalyst in the preparation of segmented [27] and cross-linked [34] PU.…”

“…Thus, glucose and sucrose are widely used in the formulations of carbohydrates-based networks [38-40, 50, 51] although other monosaccharide and disaccharide derivatives such as xylaric acid [37], maltose [36], and glucosides [51] have also been chosen (Table 4). For example, Ates et al [34,36] prepared some non-aromatic cross-linked polyurethanes with potential use as surgical tissue adhesives. PEG diol 81 and 4,4'-methylenebis(cyclohexyl isocyanate) (MCHI, 82) were polymerized with a certain amount of a sugar (maltose, sucrose, or xylose) as cross-linker.…”

“…The reaction was carried out in THF or DMF-THF mixtures, at high temperatures in the absence of catalyst or adding triethylamine (TEA). The material cross-linked with xylose 55 [34] displayed high adhesiveness and biocompatibility properties, making it suitable for being used in the medical field. Depending on the final use of the cross-linked material, the reaction can be conducted in bulk [33,38,40,50].…”

“…In order to enhance degradability, a series of homo-and copolyurethanes containing the hydrophilic monomer [triethylene glycol (TEG)] and 1,4-di-S-benzyl-D,L-dithiothreitol (DTTSBn) (34) with HDI (3) [19] was synthesized ( Figure 17). Enzymatic degradation studies were carried out with a variety of proteolytic and esterase enzymes.…”

Scalable Synthesis of Multifunctional Epidermis‐Like Smart Coatings

“…The lap‐shear test is carried out to quantitatively study the adhesive properties on different substrates. Compared with PVA, these smart coatings have increased adhesion strengths (Figure b), reaching ≈0.5–0.7 MPa, which can be comparable with other adhesive materials . We believe the polyphenolic structure of TA may enhance the adhesive properties by mimicking the molecular structure of mussel adhesive proteins .…”