Institute for Organic Chemistry and Chemical Biology, Goethe University Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt, Germany.
Chemistry. 2023 May 26;29(30):e202300390. doi: 10.1002/chem.202300390. Epub 2023 Apr 14.
The possibilities of dicyanocoumarin (DCCM)-modified oligonucleotides are expanded to not just allow their release and therefore activation with green light (OFF→ON) but to also now offer a solution for their fragmentation after exposure to green light (ON→OFF). Furthermore, an answer to the decreasing uncaging quantum yields often faced when working with red-shifted photocages is given and showed that rigidified DCCM 5'-caps outperform their predecessors. Those two new 5'-caps with ATTO 390 motif or julolidine core are compatible with copper(I)-catalyzed alkyne-azide cycloadditions (CuAACs) and therefore suitable for efficient caging through cyclization or more bioconjugation reactions. Due to their planarization, they even experience an additional red-shift which is important for their use in biological applications.
二氰基香豆素（DCCM）修饰的寡核苷酸的可能性不仅扩展为仅允许用绿光释放和因此激活（OFF→ON），而且现在还提供了在暴露于绿光后（ON→OFF）对其进行碎片化的解决方案。此外，还给出了针对在使用红移光解笼时经常遇到的未解笼量子产率降低的问题的答案，并表明刚性化的 DCCM 5'-帽比其前体更优越。带有 ATTO 390 基序或 julolidine 核的这两种新型 5'-帽与铜（I）催化的炔烃-叠氮化物环加成（CuAAC）兼容，因此适合通过环化或更多生物缀合反应进行有效的笼封。由于它们的平面化，它们甚至经历了额外的红移，这对于它们在生物应用中的使用很重要。
