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通过后聚合修饰将基于 1,6-庚二炔的环聚合物官能化以结合甘露糖,用于蛋白质相互作用。

1,6-heptadiynes based cyclopolymerization functionalized with mannose by post polymer modification for protein interaction.

机构信息

Polymer Research Centre, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur Campus, Nadia, West Bengal, 741246, India.

Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia, 741246, India.

出版信息

Carbohydr Res. 2021 Oct;508:108397. doi: 10.1016/j.carres.2021.108397. Epub 2021 Jul 12.

Abstract

Carbohydrate functionalized polymers or Glycopolymers have earned a great deal of interest in recent times for their potential biomedical applications. In the present study, a mannose containing glycopolymer was synthesized by cyclopolymerization of malonic acid derivative using second generation Hoveyda Grubbs' catalyst. Post-polymerization modification was done to install a propargyl moiety. Finally, functionalization of the propargylated polymer with 2-azidoethyl mannoside using azide-alkyne "click chemistry" furnished the target glycopolymer which was successfully characterized using NMR, FT-IR, mass spectroscopy and advanced polymer chromatography. The glycopolymer was found to self-assemble into capsule and spherical shape in water and DMSO respectively and these morphologies were observed through SEM and TEM. Upon interaction with Con A, the mannose containing glycopolymer showed an increment in aggregation induced fluorescence with increasing concentration of the lectin. In vitro cytotoxicity studies on MCF 7 cell line showed 90% cell viability up to glycopolymer concentration of 500 μg/mL.

摘要

近年来,具有生物医学应用潜力的碳水化合物功能化聚合物或糖聚合物引起了极大的关注。在本研究中,通过第二代 Hoveyda Grubbs 催化剂聚合丙二酸衍生物合成了含有甘露糖的糖聚合物。进行了聚合后修饰以安装炔丙基部分。最后,通过叠氮化物-炔烃“点击化学”将 2-叠氮乙基甘露糖苷官能化到炔丙基化聚合物上,得到了目标糖聚合物,并用 NMR、FT-IR、质谱和高级聚合物色谱法成功进行了表征。在水中和 DMSO 中,糖聚合物分别自组装成胶囊和球形,通过 SEM 和 TEM 观察到这些形态。与 Con A 相互作用时,含有甘露糖的糖聚合物在凝集素浓度增加时表现出聚集诱导荧光的增加。在 MCF 7 细胞系上的体外细胞毒性研究表明,高达 500μg/mL 的糖聚合物浓度时细胞存活率为 90%。

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