Glutathione-mediated biodegradable polyurethanes derived from L-arabinitol

Area of Science:

• Polymer Chemistry
• Biomaterials Science
• Organic Synthesis

Background:

• Development of biodegradable polymers is crucial for biomedical applications.
• Sugar-based polymers offer biocompatibility and tunable properties.
• Glutathione-mediated degradation is a promising strategy for targeted drug delivery.

Purpose of the Study:

• To synthesize novel glutathione-mediated biodegradable sugar-based copolyurethanes.
• To characterize the synthesized copolyurethanes and evaluate their thermal and degradation properties.
• To investigate the influence of copolymer composition and crystallinity on degradation behavior.

Main Methods:

• Polyaddition reaction of 2,2'-dithiodiethanol (DiT) and arabinitol derivatives (ArBn or ArMe) with 1,6-hexamethylene diisocyanate (HMDI).
• Characterization using elemental microanalyses and 1H NMR spectroscopy.
• Thermal analysis (TG curves) and assessment of biodegradability under physiological conditions (pH 7.02, 37°C) in the presence of glutathione.

Main Results:

• Copolymer composition closely matched feed ratios.
• Introduction of arabinitol units reduced crystallinity compared to the PU(DiT-HMDI) homopolymer.
• All copolyurethanes exhibited thermal stability (degradation > 220°C) and were biodegradable in the presence of glutathione.
• Degradation rate was influenced by DiT content and macromolecule crystallinity.

Conclusions:

• Novel sugar-based copolyurethanes with tunable properties and glutathione-mediated biodegradability were successfully synthesized.
• These materials demonstrate good thermal stability and biodegradability, making them suitable for further investigation in biomedical fields.
• The findings highlight the potential of incorporating sugar-derived diols into polyurethane backbones for controlled degradation applications.