Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan 430072, PR China.
Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry, Wuhan University, Wuhan 430072, PR China.
Carbohydr Polym. 2017 Aug 1;169:332-340. doi: 10.1016/j.carbpol.2017.04.028. Epub 2017 Apr 18.
This paper reports injectable hyaluronic acid (HA)-based hydrogels crosslinked with azide-modified poly(ethylene glycol) (PEG) via the strain-promoted azide-alkyne cycloaddition (SPAAC) between cyclooctyne and azide groups. Cyclooctyne-modified HA (Cyclooctyne-HA) is prepared by the reaction of HA with 2-(aminoethoxy)cyclooctyne. To crosslink the modified HA, quadruply azide-terminated poly(ethylene glycol) (Azide-PEG) is designed and prepared. The mixture of Cyclooctyne-HA and Azide-PEG gelates in a few minutes to form a strong HA-PEG hydrogel. The hydrogel has fast gelation time, good strength, and slow degradation rate, because of the high reactivity of SPAAC, high crosslinking density originated from the quadruply-substituted Azide-PEG, and the good stability of the crosslinking amide bonds. In vitro cell culturing within the hydrogel demonstrated an excellent cell-compatibility. The bioorthogonality of SPAAC makes the hydrogel injectable. With good mechanical properties and biocompatibility, the hydrogel would be useful in a wide range of applications such as injection filling materials for plastic surgery.
本文报道了通过环辛炔和叠氮基团之间的应变促进叠氮-炔环加成（SPAAC）反应，将带有叠氮基团的修饰聚乙二醇（PEG）交联到透明质酸（HA）形成的可注射水凝胶。通过 HA 与 2-（乙氧基氨）环辛炔的反应制备了环辛炔修饰的 HA（Cyclooctyne-HA）。为了交联修饰的 HA，设计并制备了四叠氮端基聚乙二醇（Azide-PEG）。Cyclooctyne-HA 和 Azide-PEG 的混合物在几分钟内凝胶化形成强的 HA-PEG 水凝胶。由于 SPAAC 的高反应性、四取代叠氮基 PEG 产生的高交联密度以及交联酰胺键的良好稳定性，水凝胶具有快速的凝胶化时间、良好的强度和缓慢的降解速率。在水凝胶内进行的体外细胞培养显示出优异的细胞相容性。SPAAC 的生物正交性使水凝胶可注射。由于具有良好的机械性能和生物相容性，该水凝胶将在广泛的应用中有用，例如整形手术的注射填充材料。
