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


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.

SUBMITTER: Heynck L 

PROVIDER: S-EPMC9297387 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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<i>N</i>-Cyanorhodamines: cell-permeant, photostable and bathochromically shifted analogues of fluoresceins.

Heynck Lukas L   Matthias Jessica J   Bossi Mariano L ML   Butkevich Alexey N AN   Hell Stefan W SW  

Chemical science 20220627 28


Fluorescein and its analogues have found only limited use in biological imaging because of the poor photostability and cell membrane impermeability of their <i>O</i>-unprotected forms. Herein, we report rationally designed <i>N</i>-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 fluores  ...[more]

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