amTCO, a newtrans-cyclooctene derivative to study drug-target interactions in cells

Cécile Echalier; Anna Rutkowska; Ana Kojic; Douglas W. Thomson; Lee J. Edwards; Blandine S.J. McKay; Marcel Mülbaier; Carsten Schultz; Giovanna Bergamini

doi:10.1039/d0cc06709a

amTCO, a newtrans-cyclooctene derivative to study drug-target interactions in cells

Cécile Echalier, Anna Rutkowska, Ana Kojic, Douglas W. Thomson, Lee J. Edwards, Blandine S.J. McKay, Marcel Mülbaier, Carsten Schultz, Giovanna Bergamini

Chemical Physiology and Biochemistry

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

2 Scopus citations

Abstract

Click chemistry probes have improved the study of drug interactions in live cells and relevant disease models. Proper design of the probes, including the choice of the click moiety coupled to the drug, is crucial to ensure good performance and broad application. A newtrans-cyclooctene derivative, amTCO, was synthesisedviaa novel route using a phthalimide protecting group as a built-in photosensitiser for the cyclooctene isomerization. amTCO improved the physical chemical properties of click chemistry probes compared to standard TCO moieties. An amTCO probe targeting indoleamine 2,3-dioxygenase (IDO1) was a superior tool for visualizing IDO1 and measuring the binding affinities of small molecule inhibitors to IDO1 in cells.

Original language	English (US)
Pages (from-to)	1814-1817
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	14
DOIs	https://doi.org/10.1039/d0cc06709a
State	Published - Feb 18 2021

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "amTCO, a newtrans-cyclooctene derivative to study drug-target interactions in cells",

abstract = "Click chemistry probes have improved the study of drug interactions in live cells and relevant disease models. Proper design of the probes, including the choice of the click moiety coupled to the drug, is crucial to ensure good performance and broad application. A newtrans-cyclooctene derivative, amTCO, was synthesisedviaa novel route using a phthalimide protecting group as a built-in photosensitiser for the cyclooctene isomerization. amTCO improved the physical chemical properties of click chemistry probes compared to standard TCO moieties. An amTCO probe targeting indoleamine 2,3-dioxygenase (IDO1) was a superior tool for visualizing IDO1 and measuring the binding affinities of small molecule inhibitors to IDO1 in cells.",

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T1 - amTCO, a newtrans-cyclooctene derivative to study drug-target interactions in cells

AU - Echalier, Cécile

AU - Rutkowska, Anna

AU - Kojic, Ana

AU - Thomson, Douglas W.

AU - Edwards, Lee J.

AU - McKay, Blandine S.J.

AU - Mülbaier, Marcel

AU - Schultz, Carsten

AU - Bergamini, Giovanna

PY - 2021/2/18

Y1 - 2021/2/18

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AB - Click chemistry probes have improved the study of drug interactions in live cells and relevant disease models. Proper design of the probes, including the choice of the click moiety coupled to the drug, is crucial to ensure good performance and broad application. A newtrans-cyclooctene derivative, amTCO, was synthesisedviaa novel route using a phthalimide protecting group as a built-in photosensitiser for the cyclooctene isomerization. amTCO improved the physical chemical properties of click chemistry probes compared to standard TCO moieties. An amTCO probe targeting indoleamine 2,3-dioxygenase (IDO1) was a superior tool for visualizing IDO1 and measuring the binding affinities of small molecule inhibitors to IDO1 in cells.

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amTCO, a newtrans-cyclooctene derivative to study drug-target interactions in cells

Abstract

ASJC Scopus subject areas

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