期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 143, 期 36, 页码 14592-14600出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c05004
关键词
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资金
- Max Planck Society
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [240245660, SFB 1129]
- German Federal Ministry of Education and Research (BMBF)
- European Research Council [CoG-724489]
- European Molecular Biology Laboratory
This article describes how the structure of rhodamines can be modified to tune the dynamic equilibrium, allowing the same rhodamine to be used to generate fluorescent probes for different purposes.
Rhodamines are the most important class of fluorophores for applications in live-cell fluorescence microscopy. This is mainly because rhodamines exist in a dynamic equilibrium between a fluorescent zwitterion and a nonfluorescent but cell-permeable spirocyclic form. Different imaging applications require different positions of this dynamic equilibrium, and an adjustment of the equilibrium poses a challenge for the design of suitable probes. We describe here how the conversion of the ortho-carboxy moiety of a given rhodamine into substituted acyl benzenesulfonamides and alkylamides permits the systematic tuning of the equilibrium of spirocyclization with unprecedented accuracy and over a large range. This allows one to transform the same rhodamine into either a highly fluorogenic and cell-permeable probe for live-cell-stimulated emission depletion (STED) microscopy or a spontaneously blinking dye for single-molecule localization microscopy (SMLM). We used this approach to generate differently colored probes optimized for different labeling systems and imaging applications.
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