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Molecular Design Boosts Hydrolytic Stability of Diisopropanolamine Boronic Ester Hydrogel for Long-Term Drug Release
Chemistry of Materials ( IF 7.2 ) Pub Date : 2024-08-03 , DOI: 10.1021/acs.chemmater.4c01027 Haifei Kang 1 , Zhangmancang Xu 2 , Ye Huang 1 , Kun Liu 1 , Wenying Wei 1 , Liupan Xu 1 , Siyuan Gao 1 , Dongjing Hong 3 , Xiaopei Wu 1 , Yan Zhao 4, 5 , Honglian Dai 1
Chemistry of Materials ( IF 7.2 ) Pub Date : 2024-08-03 , DOI: 10.1021/acs.chemmater.4c01027 Haifei Kang 1 , Zhangmancang Xu 2 , Ye Huang 1 , Kun Liu 1 , Wenying Wei 1 , Liupan Xu 1 , Siyuan Gao 1 , Dongjing Hong 3 , Xiaopei Wu 1 , Yan Zhao 4, 5 , Honglian Dai 1
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Boronic ester hydrogels are widely used in biomedicine for their stimulus responsiveness to multiple disease-related triggers. However, their applicability is limited by its low hydrolytic stability. Here, we created the highest hydrolytically stable boronic ester cross-linked network yet documented─novel diisopropanolamine boronic ester (DIPAB) hydrogel. The systematic study from a molecular level to a three-dimensional hydrogel network demonstrates that DIPAB has significantly greater hydrolytic stability and dynamic exchange activation energy than diethanolamine boronic ester (DEAB). Based on molecular structure and electron density analyses, the results clarify that the improved hydrolytic stability of DIPAB is attributable to the introduction of a methyl group, which enhances the conjugation effect of the molecule, the steric effect, and the covalent character of the boron nitrogen coordination bond (BNCB), and reduces the tension of the five-membered ring. The relative potential energy of the hydrolytic process of DIPAB is identified by applying density functional theory (DFT) calculations. Finally, tazarotene-loaded DIPAB hydrogels are created and prepared for sustained drug release, significantly promoting rat skin healing. We anticipate that this innovative DIPAB hydrogel will open up a new design strategy for responsive drug carriers, dynamic chemically bonded hydrogels, and recyclable cross-linked polymers. Furthermore, our findings may encourage other structural alterations of diethanolamine to improve the adaptability of the boronic ester bonds for different application conditions.
中文翻译：
分子设计提高二异丙醇胺硼酸酯水凝胶的水解稳定性，实现药物的长期释放
硼酸酯水凝胶因其对多种疾病相关触发因素的刺激反应而被广泛应用于生物医学。然而，它们的适用性因其低水解稳定性而受到限制。在这里，我们创造了迄今为止有记录的最高水解稳定性的硼酸酯交联网络——新型二异丙醇胺硼酸酯（DIPAB）水凝胶。从分子水平到三维水凝胶网络的系统研究表明，DIPAB比二乙醇胺硼酸酯（DEAB）具有明显更高的水解稳定性和动态交换活化能。基于分子结构和电子密度分析，结果表明 DIPAB 水解稳定性的提高归因于甲基的引入，甲基增强了分子的共轭效应、空间效应和硼氮的共价特性配位键（BNCB），降低五元环的张力。 DIPAB 水解过程的相对势能通过应用密度泛函理论 (DFT) 计算来确定。最后，创建并制备了负载他扎罗汀的 DIPAB 水凝胶，用于持续药物释放，显着促进大鼠皮肤愈合。我们预计这种创新的 DIPAB 水凝胶将为响应性药物载体、动态化学键合水凝胶和可回收交联聚合物开辟新的设计策略。此外，我们的研究结果可能鼓励二乙醇胺的其他结构改变，以提高硼酸酯键对不同应用条件的适应性。
更新日期：2024-08-03
中文翻译：
分子设计提高二异丙醇胺硼酸酯水凝胶的水解稳定性，实现药物的长期释放
硼酸酯水凝胶因其对多种疾病相关触发因素的刺激反应而被广泛应用于生物医学。然而，它们的适用性因其低水解稳定性而受到限制。在这里，我们创造了迄今为止有记录的最高水解稳定性的硼酸酯交联网络——新型二异丙醇胺硼酸酯（DIPAB）水凝胶。从分子水平到三维水凝胶网络的系统研究表明，DIPAB比二乙醇胺硼酸酯（DEAB）具有明显更高的水解稳定性和动态交换活化能。基于分子结构和电子密度分析，结果表明 DIPAB 水解稳定性的提高归因于甲基的引入，甲基增强了分子的共轭效应、空间效应和硼氮的共价特性配位键（BNCB），降低五元环的张力。 DIPAB 水解过程的相对势能通过应用密度泛函理论 (DFT) 计算来确定。最后，创建并制备了负载他扎罗汀的 DIPAB 水凝胶，用于持续药物释放，显着促进大鼠皮肤愈合。我们预计这种创新的 DIPAB 水凝胶将为响应性药物载体、动态化学键合水凝胶和可回收交联聚合物开辟新的设计策略。此外，我们的研究结果可能鼓励二乙醇胺的其他结构改变，以提高硼酸酯键对不同应用条件的适应性。
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