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绿色至远红色发射的荧光四嗪探针——合成方法及活细胞内免洗蛋白质成像

Green- to far-red-emitting fluorogenic tetrazine probes - synthetic access and no-wash protein imaging inside living cells.

作者信息

Wieczorek Achim, Werther Philipp, Euchner Jonas, Wombacher Richard

机构信息

Institut für Pharmazie und Molekulare Biotechnologie , Ruprecht-Karls-Universität Heidelberg , Im Neuenheimer Feld 364 , 69120 Heidelberg , Germany . Email:

出版信息

Chem Sci. 2017 Feb 1;8(2):1506-1510. doi: 10.1039/c6sc03879d. Epub 2016 Oct 21.

DOI:10.1039/c6sc03879d
PMID:28572909
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5452268/
Abstract

Fluorogenic probes for bioorthogonal labeling chemistry are highly beneficial to reduce background signal in fluorescence microscopy imaging. 1,2,4,5-Tetrazines are known substrates for the bioorthogonal inverse electron demand Diels-Alder reaction (DA) and tetrazine substituted fluorophores can exhibit fluorogenic properties. Herein, we report the synthesis of a palette of novel fluorogenic tetrazine dyes derived from widely-used fluorophores that cover the entire emission range from green to far-red. We demonstrate the power of the new fluorogenic probes in fixed and live cell labeling experiments and present the first example of intracellular live cell protein imaging using tetrazine-based probes under no-wash conditions.

摘要

用于生物正交标记化学的荧光探针对于减少荧光显微镜成像中的背景信号非常有益。1,2,4,5-四嗪是生物正交逆电子需求狄尔斯-阿尔德反应(DA反应)的已知底物,并且四嗪取代的荧光团可以表现出荧光特性。在此,我们报告了一系列新型荧光四嗪染料的合成,这些染料源自广泛使用的荧光团,覆盖了从绿色到远红色的整个发射范围。我们展示了新型荧光探针在固定细胞和活细胞标记实验中的强大功能,并展示了在无需洗涤条件下使用基于四嗪的探针进行细胞内活细胞蛋白质成像的首个实例。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/c620b6323344/c6sc03879d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/ddf8a5c8fcd8/c6sc03879d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/1b3205a9864c/c6sc03879d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/c407fca0d4eb/c6sc03879d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/c620b6323344/c6sc03879d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/ddf8a5c8fcd8/c6sc03879d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/1b3205a9864c/c6sc03879d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/c407fca0d4eb/c6sc03879d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d5c/5452268/c620b6323344/c6sc03879d-f4.jpg

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