Membrane-Permeant, Bioactivatable Coumarin Derivatives for In-Cell Labelling

Madeleine Schultz; Rainer Müller; Yulia Ermakova; Jan Erik Hoffmann; Carsten Schultz

doi:10.1002/cbic.202100699

Membrane-Permeant, Bioactivatable Coumarin Derivatives for In-Cell Labelling

Madeleine Schultz, Rainer Müller, Yulia Ermakova, Jan Erik Hoffmann, Carsten Schultz

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The delivery of small molecule fluorophores with minimal compartmentalization is currently one of the most critical technical problems in intracellular labelling. Here we introduce sulfonated and phosphonated coumarin dyes, demonstrate rapid cell entry via a prodrug approach, and show a lack of interaction with membranes, organelles, or other compartments. The dyes show no specific localization and are evenly distributed in the cells. Our fluorogenic, clickable phosphonate derivatives successfully tagged model targets in intact cells and the increase in brightness upon click reaction was around 60-fold.

Original language	English (US)
Article number	e202100699
Journal	ChemBioChem
Volume	23
Issue number	6
DOIs	https://doi.org/10.1002/cbic.202100699
State	Published - Mar 18 2022
Externally published	Yes

Keywords

cellular location
click chemistry
fluorogenic dyes
live-cell imaging
membrane permeable dyes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.202100699

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title = "Membrane-Permeant, Bioactivatable Coumarin Derivatives for In-Cell Labelling",

abstract = "The delivery of small molecule fluorophores with minimal compartmentalization is currently one of the most critical technical problems in intracellular labelling. Here we introduce sulfonated and phosphonated coumarin dyes, demonstrate rapid cell entry via a prodrug approach, and show a lack of interaction with membranes, organelles, or other compartments. The dyes show no specific localization and are evenly distributed in the cells. Our fluorogenic, clickable phosphonate derivatives successfully tagged model targets in intact cells and the increase in brightness upon click reaction was around 60-fold.",

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author = "Madeleine Schultz and Rainer M{\"u}ller and Yulia Ermakova and Hoffmann, {Jan Erik} and Carsten Schultz",

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AU - Schultz, Madeleine

AU - Müller, Rainer

AU - Ermakova, Yulia

AU - Hoffmann, Jan Erik

AU - Schultz, Carsten

PY - 2022/3/18

Y1 - 2022/3/18

N2 - The delivery of small molecule fluorophores with minimal compartmentalization is currently one of the most critical technical problems in intracellular labelling. Here we introduce sulfonated and phosphonated coumarin dyes, demonstrate rapid cell entry via a prodrug approach, and show a lack of interaction with membranes, organelles, or other compartments. The dyes show no specific localization and are evenly distributed in the cells. Our fluorogenic, clickable phosphonate derivatives successfully tagged model targets in intact cells and the increase in brightness upon click reaction was around 60-fold.

AB - The delivery of small molecule fluorophores with minimal compartmentalization is currently one of the most critical technical problems in intracellular labelling. Here we introduce sulfonated and phosphonated coumarin dyes, demonstrate rapid cell entry via a prodrug approach, and show a lack of interaction with membranes, organelles, or other compartments. The dyes show no specific localization and are evenly distributed in the cells. Our fluorogenic, clickable phosphonate derivatives successfully tagged model targets in intact cells and the increase in brightness upon click reaction was around 60-fold.

KW - cellular location

KW - click chemistry

KW - fluorogenic dyes

KW - live-cell imaging

KW - membrane permeable dyes

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VL - 23

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ER -

Membrane-Permeant, Bioactivatable Coumarin Derivatives for In-Cell Labelling

Abstract

Keywords

ASJC Scopus subject areas

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