A Concise Synthetic Approach to Highly Reactive Click-to-Release Trans-Cyclooctene Linkers

被引：5
|
作者：
Liu, Bing [1 ]
ten Hoeve, Wolter [2 ]
Versteegen, Ron M. [3 ]
Rossin, Raffaella [1 ]
Kleijn, Laurens H. J. [1 ]
Robillard, Marc S. [1 ]
机构：
[1] Tagworks Pharmaceut, Toernooiveld 1, NL-6525 ED Nijmegen, Netherlands
[2] Symeres, Kadijk 3, NL-9747 AT Groningen, Netherlands
[3] SyMO Chem, Den Dolech 2, NL-5612 AZ Eindhoven, Netherlands
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 45期
关键词：
cleavable linkers; click chemistry; iodolactonization; pyridazine elimination; trans-cyclooctene; IMPROVED STABILITY; CHEMISTRY; DIENOPHILES; ACTIVATION; DESIGN;
D O I：
10.1002/chem.202300755
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An increase in the click-to-release reaction rate between cleavable trans-cyclooctenes (TCO) and tetrazines would be beneficial for drug delivery applications. In this work, we have developed a short and stereoselective synthesis route towards highly reactive sTCOs that serve as cleavable linkers, affording quantitative tetrazine-triggered payload release. In addition, the fivefold more reactive sTCO exhibited the same in vivo stability as current TCO linkers when used as antibody linkers in circulation in mice.
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页数：5
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