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Cysteine specific bioconjugation with benzyl isothiocyanates

Petri, L; Szijj, PA; Kelemen, Á; Imre, T; Gömöry, Á; Lee, MTW; Hegedűs, K; ... Keserű, GM; + view all (2020) Cysteine specific bioconjugation with benzyl isothiocyanates. RSC Advances , 10 (25) pp. 14928-14936. 10.1039/d0ra02934c. Green open access

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Abstract

Protein labelling has a wide variety of applications in medicinal chemistry and chemical biology. In addition to covalent inhibition, specific labelling of biomolecules with fluorescent dyes is important in both target discovery, validation and diagnostics. Our research was conducted through the fragment-based development of a new benzyl-isothiocyanate-activated fluorescent dye based on the fluorescein scaffold. This molecule was evaluated against fluorescein isothiocyanate, a prevalent labelling agent. The reactivity and selectivity of phenyl- and benzyl isothiocyanate were compared at different pHs, and their activity was tested on several protein targets. Finally, the clinically approved antibody trastuzumab (and it's Fab fragment) were specifically labelled through reaction with free cysteines reductively liberated from their interchain disulfide bonds. The newly developed benzyl-fluorescein isothiocyanate and its optimized labelling protocol stands to be a valuable addition to the tool kit of chemical biology.

Type: Article
Title: Cysteine specific bioconjugation with benzyl isothiocyanates
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/d0ra02934c
Publisher version: https://doi.org/10.1039/D0RA02934C
Language: English
Additional information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10095193
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