English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

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

MPS-Authors
/persons/resource/persons222860

Bucevicius,  J.
Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons249610

Kostiuk,  G.
Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons220611

Gerasimaite,  R.
Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons230579

Gilat,  T.
Department of NanoBiophotonics, MPI for Biophysical Chemistry, Max Planck Society;

/persons/resource/persons203920

Lukinavicius,  G.
Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society;

External Resource
No external resources are shared
Fulltext (public)

3257488.pdf
(Publisher version), 9MB

Supplementary Material (public)
There is no public supplementary material available
Citation

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.


Cite as: http://hdl.handle.net/21.11116/0000-0007-2C4D-3
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.