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Issue 28, 2020
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Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect

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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.

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

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Supplementary files

Article information


Submitted
15 Apr 2020
Accepted
20 Jun 2020
First published
22 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7313-7323
Article type
Edge Article

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

J. Bucevičius, G. Kostiuk, R. Gerasimaitė, T. Gilat and G. Lukinavičius, Chem. Sci., 2020, 11, 7313
DOI: 10.1039/D0SC02154G

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