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Journal Article

N-Cyanorhodamines: cell-permeant, photostable and bathochromically shifted analogues of fluoresceins

MPS-Authors
/persons/resource/persons275836

Heynck,  Lukas
Optical Nanoscopy, Max Planck Institute for Medical Research, Max Planck Society;

/persons/resource/persons275838

Matthias,  Jessica
Optical Nanoscopy, Max Planck Institute for Medical Research, Max Planck Society;

/persons/resource/persons191595

Butkevich,  Alexey N.
Optical Nanoscopy, Max Planck Institute for Medical Research, Max Planck Society;

/persons/resource/persons15210

Hell,  Stefan W.
Optical Nanoscopy, Max Planck Institute for Medical Research, Max Planck Society;

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https://pubs.rsc.org/en/content/articlelanding/2022/sc/d2sc02448a
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https://pubs.rsc.org/en/content/articlepdf/2022/sc/d2sc02448a
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https://www.rsc.org/suppdata/d2/sc/d2sc02448a/d2sc02448a1.pdf
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Citation

Heynck, L., Matthias, J., Bossi, M. L., Butkevich, A. N., & Hell, S. W. (2022). N-Cyanorhodamines: cell-permeant, photostable and bathochromically shifted analogues of fluoresceins. Chemical Science, 13(28), 8297-8306. doi:10.1039/d2sc02448a.


Cite as: https://hdl.handle.net/21.11116/0000-000A-B014-8
Abstract
Fluorescein and its analogues have found only limited use in biological imaging because of the poor photostability and cell membrane impermeability of their O-unprotected forms. Herein, we report rationally designed N-cyanorhodamines as orange- to red-emitting, photostable and cell-permeant fluorescent labels negatively charged at physiological pH values and thus devoid of off-targeting artifacts often observed for cationic fluorophores. In combination with well-established fluorescent labels, self-labelling protein (HaloTag, SNAP-tag) ligands derived from N-cyanorhodamines permit up to four-colour confocal and super-resolution STED imaging in living cells.