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Systematic Tuning of Rhodamine Spirocyclization for Super-resolution Microscopy
Open accessAbstract
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.
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Cited by
Zeng, S., Liu, X., Kafuti, Y. S., Kim, H., Wang, J., Peng, X., Li, H., & Yoon, J. (2023) · Chemical Society Reviews · doi:10.1039/d2cs00799a · Cited by 341
SNAP-tag2 for faster and brighter protein labeling
Kühn, S., Nasufovic, V., Wilhelm, J., Kompa, J., de Lange, E. M. F., Lin, Y.-H., Egoldt, C., Fischer, J., Lennoi, A., Tarnawski, M., et al. (2025) · Nature Chemical Biology · doi:10.1038/s41589-025-01942-z · Cited by 44
Self-citationWu, F., Zheng, B., Qiu, X., Hu, T., Yang, Y., Yang, K., Zhou, B., Ma, Q., Pang, D., & Xiong, H. (2025) · Angewandte Chemie International Edition · doi:10.1002/anie.202423059 · Cited by 18
Zhang, M., Jin, L., Zhu, Y., Kou, J., Liu, B., Chen, J., Zhong, X., Wu, X., Zhang, J., & Ren, W. (2025) · Chinese Chemical Letters · doi:10.1016/j.cclet.2024.110772 · Cited by 5
Metadata
- Authors
- Lardon, N., Wang, L., Tschanz, A., Hoess, P., Tran, M., D’Este, E., Ries, J., & Johnsson, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2021-08-30
- Volume
- 143
- Issue
- 36
- Pages
- 14592-14600
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W3197096057
- Cited by
- 177
- References
- 0
- FWCI
- 11.84
- Type
- journal article
- Language
- en
- Open access
- green
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- Lardon, N., Wang, L., Tschanz, A., Hoess, P., Tran, M., D’Este, E., Ries, J., & Johnsson, K. (2021). Systematic Tuning of Rhodamine Spirocyclization for Super-resolution Microscopy. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.1c05004
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