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Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy

Nicolas Lardon, View ORCID ProfileLu Wang, View ORCID ProfileAline Tschanz, View ORCID ProfilePhilipp Hoess, View ORCID ProfileMai Tran, View ORCID ProfileElisa D’Este, View ORCID ProfileJonas Ries, View ORCID ProfileKai Johnsson
doi: https://doi.org/10.1101/2021.05.20.444797
Nicolas Lardon
1Department of Chemical Biology, Max Planck Institute for Medical Research, Jahnstrasse 29, Heidelberg, Germany
2Faculty of Chemistry and Earth Sciences, Heidelberg University, Heidelberg, Germany
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Lu Wang
1Department of Chemical Biology, Max Planck Institute for Medical Research, Jahnstrasse 29, Heidelberg, Germany
7Key Laboratory of Smart Drug Delivery, Ministry of Education, School of Pharmacy, Fudan University, Zhangheng Road 826, Shanghai, China
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  • For correspondence: Johnsson@mr.mpg.de Lu.Wang@mr.mpg.de
Aline Tschanz
3Cell Biology and Biophysics Unit, European Molecular Biology Laboratory (EMBL), Meyerhofstrasse 1, Heidelberg, Germany
4Collaboration for joint PhD degree between EMBL and Heidelberg University, Faculty of Biosciences, Heidelberg, Germany
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Philipp Hoess
3Cell Biology and Biophysics Unit, European Molecular Biology Laboratory (EMBL), Meyerhofstrasse 1, Heidelberg, Germany
4Collaboration for joint PhD degree between EMBL and Heidelberg University, Faculty of Biosciences, Heidelberg, Germany
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Mai Tran
1Department of Chemical Biology, Max Planck Institute for Medical Research, Jahnstrasse 29, Heidelberg, Germany
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Elisa D’Este
5Optical Microscopy Facility, Max Planck Institute for Medical Research, Jahnstrasse 29, Heidelberg, Germany
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Jonas Ries
3Cell Biology and Biophysics Unit, European Molecular Biology Laboratory (EMBL), Meyerhofstrasse 1, Heidelberg, Germany
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Kai Johnsson
1Department of Chemical Biology, Max Planck Institute for Medical Research, Jahnstrasse 29, Heidelberg, Germany
6Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland
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  • ORCID record for Kai Johnsson
  • For correspondence: Johnsson@mr.mpg.de Lu.Wang@mr.mpg.de
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Abstract

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 non-fluorescent but cell-permeable spirocyclic form. Different imaging applications require different positions of this dynamic equilibrium, which 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 to transform the same rhodamine into either a highly fluorogenic and cell-permeable probe for live-cell stimulated emission depletion (STED) microscopy, or into 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.

Competing Interest Statement

The authors declare the following competing financial interest(s): K.J. and L.W. are inventors of the patent Cell-permeable fluorogenic fluorophores which was filed by the Max Planck Society.

Copyright 
The copyright holder for this preprint is the author/funder, who has granted bioRxiv a license to display the preprint in perpetuity. It is made available under a CC-BY 4.0 International license.
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Posted May 20, 2021.
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Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy
Nicolas Lardon, Lu Wang, Aline Tschanz, Philipp Hoess, Mai Tran, Elisa D’Este, Jonas Ries, Kai Johnsson
bioRxiv 2021.05.20.444797; doi: https://doi.org/10.1101/2021.05.20.444797
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Systematic Tuning of Rhodamine Spirocyclization for Super-Resolution Microscopy
Nicolas Lardon, Lu Wang, Aline Tschanz, Philipp Hoess, Mai Tran, Elisa D’Este, Jonas Ries, Kai Johnsson
bioRxiv 2021.05.20.444797; doi: https://doi.org/10.1101/2021.05.20.444797

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