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  Systematic tuning of rhodamine spirocyclization for super-resolution microscopy

Lardon, N., Wang, L., Tschanz, A., Hoess, P., Tran, M., D´Este, E., et al. (2021). Systematic tuning of rhodamine spirocyclization for super-resolution microscopy. Journal of the American Chemical Society, 143(36), 14592-14600. doi:10.1021/jacs.1c05004.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0009-A1F7-A Version Permalink: https://hdl.handle.net/21.11116/0000-0009-A1F8-9
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 Creators:
Lardon, Nicolas1, Author           
Wang, Lu1, Author           
Tschanz, Aline, Author
Hoess, Philipp, Author
Tran, Mai1, Author           
D´Este, Elisa2, Author           
Ries, Jonas, Author
Johnsson, Kai1, Author           
Affiliations:
1Chemical Biology, Max Planck Institute for Medical Research, Max Planck Society, ou_2364732              
2Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              

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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 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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Language(s): eng - English
 Dates: 2021-05-142021-08-302021-09-15
 Publication Status: Issued
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.1c05004
URI: https://pubmed.ncbi.nlm.nih.gov/34460256/
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 143 (36) Sequence Number: - Start / End Page: 14592 - 14600 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870