生物正交释放磺胺类药物和两种药物的相互正交释放。
Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs.
机构信息
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
出版信息
Chem Commun (Camb). 2018 Dec 13;54(100):14089-14092. doi: 10.1039/c8cc08533a.
Abstract
Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.
摘要
磺胺衍生物在药剂学中已经使用了几十年。在这里，我们报告了一种使用磺酰基吖丙啶和二苯并氮杂环辛炔（DIBAC）的生物正交反应来有效释放磺胺类药物的新方法。环加成反应的二级速率常数可达 0.62 M-1 s-1，并且反应物在生理条件下非常稳定。最重要的是，我们还发现了 sydnonimine-DIBAC 和 benzonorbornadiene-tetrazine 环加成对之间的相互正交性，可用于选择性和同时释放磺胺类和伯胺类药物。
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