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  Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect

Bucevicius, J., Kostiuk, G., Gerasimaite, R., Gilat, T., & Lukinavicius, G. (2020). Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect. Chemical Science, 11(28), 7313-7323. doi:10.1039/D0SC02154G.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0007-2C4D-3 Version Permalink: http://hdl.handle.net/21.11116/0000-0007-2C50-E
Genre: Journal Article

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Bucevicius, J.1, Author              
Kostiuk, G.1, Author              
Gerasimaite, R.1, Author              
Gilat, T.2, Author              
Lukinavicius, G.1, Author              
Affiliations:
1Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society, ou_2616691              
2Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society, ou_578627              

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 Abstract: Fluorescence microscopy is an essential tool for understanding dynamic processes in living cells and organisms. However, many fluorescent probes for labelling cellular structures suffer from unspecific interactions and low cell permeability. Herein, we demonstrate that the neighbouring group effect which results from positioning an amide group next to a carboxyl group in the benzene ring of rhodamines dramatically increases cell permeability of the rhodamine-based probes through stabilizing a fluorophore in a hydrophobic spirolactone state. Based on this principle, we create probes targeting tubulin, actin and DNA. Their superb staining intensity, tuned toxicity and specificity allows long-term 3D confocal and STED nanoscopy with sub-30 nm resolution. Due to their unrestricted cell permeability and efficient accumulation on the target, the new probes produce high contrast images at low nanomolar concentrations. Superior performance is exemplified by resolving the real microtubule diameter of 23 nm and selective staining of the centrosome inside living cells for the first time.

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Language(s): eng - English
 Dates: 2020-06-222020-07-28
 Publication Status: Published in print
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 Rev. Type: Peer
 Identifiers: DOI: 10.1039/D0SC02154G
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Title: Chemical Science
Source Genre: Journal
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Pages: - Volume / Issue: 11 (28) Sequence Number: - Start / End Page: 7313 - 7323 Identifier: -