Sakhaii Peyman, Bohorc Bojan, Olpp Thomas, Mohnicke Mandy, Rieke-Zapp Joerg, Dhal Pradeep K
Global CMC Development, Global R&D, Sanofi, Industrial Park Hoechst, D-65926, Frankfurt/Main, Germany.
Manufacturing Science and Analytical Technology, Sanofi, Industrial Park Hoechst, D- 65926, Frankfurt/Main, Germany.
Sci Rep. 2024 Nov 19;14(1):28612. doi: 10.1038/s41598-024-78731-6.
Applications of functionalized hyaluronic acid (HA) hydrogels for numerous biomedical applications requires their detailed structural characterization. Since these materials are prepared by multistep chemical modifications in the solid phase and not amenable to characterization by standard analytical tools, we employed high-resolution solid-state NMR spectroscopy to gain detailed insights into the structures of the functionalized HA hydrogels. Divinyl sulfone crosslinked HA hydrogels were converted into maleimide-functionalized hydrogels, which were subjected to chemoselective thiol-maleimide reaction using L-cysteine as the protein mimetic thiol reagent. To overcome challenges associated with obtaining high-resolution NMR spectra of crosslinked hydrogels (such as line broadening and overlapping of signals of the hydrogel with those of residual reagents and solvents used during multi-step reaction processes on insoluble polymer matrices), we devised a radio frequency mediated diffusion-edited semi solid-state NMR technique. This technique enabled us to record NMR spectra of hydrogels exclusively by effectively suppressing signals associated with low molecular weight impurities. Thus, it became possible to perform in-depth characterization of these chemically modified HA hydrogels including quantification of reaction outcome for each reaction step.
功能化透明质酸(HA)水凝胶在众多生物医学应用中的应用需要对其详细的结构进行表征。由于这些材料是通过多步固相化学修饰制备的,并且不适用于用标准分析工具进行表征,因此我们采用高分辨率固态核磁共振光谱来深入了解功能化HA水凝胶的结构。二乙烯基砜交联的HA水凝胶被转化为马来酰亚胺功能化水凝胶,然后使用L-半胱氨酸作为蛋白质模拟硫醇试剂进行化学选择性硫醇-马来酰亚胺反应。为了克服与获得交联水凝胶的高分辨率核磁共振光谱相关的挑战(例如线宽展宽以及水凝胶信号与在不溶性聚合物基质上的多步反应过程中使用的残留试剂和溶剂的信号重叠),我们设计了一种射频介导的扩散编辑半固态核磁共振技术。该技术使我们能够通过有效抑制与低分子量杂质相关的信号来专门记录水凝胶的核磁共振光谱。因此,对这些化学修饰的HA水凝胶进行深入表征成为可能,包括对每个反应步骤的反应结果进行量化。