Methyltetrazine as a small live-cell compatible bioorthogonal handle for imaging enzyme activities

Bioorthogonal chemistry combines well with activity-based protein profiling, as it allows for the introduction of detection tags without significantly influencing the physiochemical and biological functions of the probe. In this work, we introduced methyltetrazinylalanine (MeTz-Ala), a close mimic o...

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Published in:RSC chemical biology 2022-11, Vol.3 (11), p.1325-133
Main Authors: Torres-García, Diana, van de Plassche, Merel A. T, van Boven, Emma, van Leeuwen, Tyrza, Groenewold, Mirjam G. J, Sarris, Alexi J. C, Klein, Luuk, Overkleeft, Herman S, van Kasteren, Sander I
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container_end_page 133
container_issue 11
container_start_page 1325
container_title RSC chemical biology
container_volume 3
creator Torres-García, Diana
van de Plassche, Merel A. T
van Boven, Emma
van Leeuwen, Tyrza
Groenewold, Mirjam G. J
Sarris, Alexi J. C
Klein, Luuk
Overkleeft, Herman S
van Kasteren, Sander I
description Bioorthogonal chemistry combines well with activity-based protein profiling, as it allows for the introduction of detection tags without significantly influencing the physiochemical and biological functions of the probe. In this work, we introduced methyltetrazinylalanine (MeTz-Ala), a close mimic of phenylalanine, into a dipeptide fluoromethylketone cysteine protease inhibitor. Following covalent and irreversible inhibition, the tetrazine allows vizualisation of the captured cathepsin activity by means of inverse electron demand Diels Alder ligation in cell lysates and live cells, demonstrating that tetrazines can be used as live cell compatible, minimal bioorthogonal tags in activity-based protein profiling. Bioorthogonal chemistry combines well with activity-based protein profiling, as it allows for the introduction of detection tags without significantly influencing the physiochemical and biological functions of the probe.
doi_str_mv 10.1039/d2cb00120a
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title Methyltetrazine as a small live-cell compatible bioorthogonal handle for imaging enzyme activities
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