Thiol click modification of cyclic disulfide containing biodegradable polyurethane urea elastomers

Area of Science:

• Polymer Chemistry
• Biomaterials Science
• Regenerative Medicine

Background:

• Thiol click chemistry is useful for polymer modification but limited by thiol oxidation.
• Stable disulfide bonds offer an alternative for covalent immobilization of bioactive molecules.

Purpose of the Study:

• To develop and characterize biodegradable polyurethane elastomers with stable cyclic disulfide groups.
• To investigate the potential for bulk and surface click modification of these polymers.
• To evaluate the utility of these materials in regenerative medicine applications.

Main Methods:

• Synthesis of poly(ester urethane)urea (PEUU-SS) polymers using polycaprolactone diol (PCL), oxidized dl-dithiothreitol (O-DTT), and diisocyanates (LDI or BDI).
• Characterization of polymer properties, including elasticity and mechanical strength.
• Evaluation of click modification efficiency (bulk and surface) using PEG acrylate and a peptide (TPS).

Main Results:

• Synthesized PEUU-SS polymers exhibited elasticity (38-45 MPa breaking strength).
• Variable bulk and rapid surface click modification were achieved under mild conditions.
• Surface modification with a peptide enhanced endothelial progenitor cell adhesion on electrospun scaffolds.

Conclusions:

• Biodegradable polyurethanes with cyclic disulfide groups offer a stable platform for click chemistry.
• These materials are suitable for creating functionalized scaffolds in soft tissue regenerative medicine.
• The approach provides a simple method for designing biofunctional, temporary medical implants.