College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China.
Shandong Tianming Pharmaceutical Co, Ltd., Jinan 250104, P. R. China.
J Mater Chem B. 2023 Jun 28;11(25):5846-5855. doi: 10.1039/d3tb00596h.
This work developed innovative poly(ester-urethane) materials double-modified by quercetin (QC) and phosphorylcholine (PC) with improved antibacterial activity and hemocompatibility. The functional monomer of PC-diol was first synthesized a click reaction between 2-methacryloyloxyethyl phosphorylcholine and α-thioglycerol; the NCO-terminated prepolymer was subsequently prepared by a one-pot condensation method of PC-diol, poly(ε-caprolactone) diol, and excess isophorone diisocyanate; finally, the prepolymer was chain-extended with QC to produce the linear products (PEU-PQs). H NMR, FT-IR, and XPS techniques confirmed the successful introduction of PC and QC, and the in-depth characterization of the cast PEU-PQ films was carried out. Although a low crystallinity was demonstrated by XRD and thermal analysis, the films exhibited excellent tensile stress and stretchability due to the interchain multiple hydrogen bonds. The introduction of PC groups enhanced the surface hydrophilicity, water absorption, and the hydrolytic degradation rate of the film materials. Inhibition zone tests presented that the QC-based PEU-PQs had effective antibacterial activity against and . The biological evaluations of the materials were performed by protein absorption, platelet adhesion, and cytotoxic test and by subcutaneous implantation, which demonstrated superior surface hemocompatibility and biocompatibility. Collectively, the PEU-PQ biomaterials hold a prospective application in durable blood-contacting devices.
本工作开发了通过槲皮素(QC)和磷酸胆碱(PC)双重改性的创新型聚(酯-氨酯)材料,具有改善的抗菌活性和血液相容性。首先通过 2-甲基丙烯酰氧基乙基磷酸胆碱和α-硫甘油之间的点击反应合成了 PC-二醇的功能单体;随后通过 PC-二醇、聚(ε-己内酯)二醇和过量异佛尔酮二异氰酸酯的一锅缩合方法制备了 NCO 端预聚物;最后,用 QC 对预聚物进行链扩展,生成线性产物(PEU-PQs)。H NMR、FT-IR 和 XPS 技术证实了 PC 和 QC 的成功引入,对铸膜的 PEU-PQ 薄膜进行了深入的表征。尽管 XRD 和热分析表明结晶度较低,但由于链间的多重氢键,薄膜表现出优异的拉伸应力和拉伸性。PC 基团的引入提高了薄膜材料的表面亲水性、吸水率和水解降解速率。抑菌圈试验表明,基于 QC 的 PEU-PQs 对 和 具有有效的抗菌活性。通过蛋白吸附、血小板黏附及细胞毒性试验和皮下植入对材料进行了生物学评价,结果表明其具有优异的表面血液相容性和生物相容性。总的来说,PEU-PQ 生物材料在耐用的血液接触装置中有很好的应用前景。