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Bio-orthogonal red and far-red fluorogenic probes for wash-free live-cell and super-resolution microscopy

Small-molecule fluorophores enable the observation of biomolecules in their native context with fluorescence microscopy. Specific labeling via bio-orthogonal tetrazine chemistry combines minimal label size with rapid labeling kinetics. At the same time, fluorogenic tetrazine-dye conjugates exhibit e...

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Main Authors: Werther, Philipp (Author) , Yserentant, Klaus (Author) , Braun, Felix (Author) , Grußmayer, Kristin Stefanie (Author) , Navikas, Vytautas (Author) , Yu, Miao (Author) , Zhang, Zhibin (Author) , Ziegler, Michael J. (Author) , Mayer, Christoph (Author) , Gralak, Antoni J. (Author) , Busch, Marvin (Author) , Chi, Weijie (Author) , Rominger, Frank (Author) , Radenovic, Aleksandra (Author) , Liu, Xiaogang (Author) , Lemke, Edward A. (Author) , Buckup, Tiago (Author) , Herten, Dirk-Peter (Author) , Wombacher, Richard (Author)
Format: Article (Journal)
Language:English
Published: August 20, 2021
In: ACS central science
Year: 2021, Volume: 7, Issue: 9, Pages: 1561-1571
ISSN:2374-7951
DOI:10.1021/acscentsci.1c00703
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1021/acscentsci.1c00703
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Author Notes:Philipp Werther, Klaus Yserentant, Felix Braun, Kristin Grußmayer, Vytautas Navikas, Miao Yu, Zhibin Zhang, Michael J. Ziegler, Christoph Mayer, Antoni J. Gralak, Marvin Busch, Weijie Chi, Frank Rominger, Aleksandra Radenovic, Xiaogang Liu, Edward A. Lemke, Tiago Buckup, Dirk-Peter Herten, and Richard Wombacher
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Summary:Small-molecule fluorophores enable the observation of biomolecules in their native context with fluorescence microscopy. Specific labeling via bio-orthogonal tetrazine chemistry combines minimal label size with rapid labeling kinetics. At the same time, fluorogenic tetrazine-dye conjugates exhibit efficient quenching of dyes prior to target binding. However, live-cell compatible long-wavelength fluorophores with strong fluorogenicity have been difficult to realize. Here, we report close proximity tetrazine-dye conjugates with minimal distance between tetrazine and the fluorophore. Two synthetic routes give access to a series of cell-permeable and -impermeable dyes including highly fluorogenic far-red emitting derivatives with electron exchange as the dominant excited-state quenching mechanism. We demonstrate their potential for live-cell imaging in combination with unnatural amino acids, wash-free multicolor and super-resolution STED, and SOFI imaging. These dyes pave the way for advanced fluorescence imaging of biomolecules with minimal label size.
Item Description:Published: August 20, 2021
Gesehen am 23.03.2022
Physical Description:Online Resource
ISSN:2374-7951
DOI:10.1021/acscentsci.1c00703

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