Diverted Natural Lossen-type Rearrangement for Bioconjugation through in Situ Myrosinase-Triggered Isothiocyanate Synthesis.

Autor: Fredy JW; Normandie Univ , CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014) , 76000 Rouen , France., Cutolo G; Institut de Chimie Organique et Analytique - ICOA UMR 7311 CNRS , Université d'Orléans , Rue de Chartres , BP6759, 45067 cedex 02 Orléans , France., Poret B; Normandie Univ , UNIROUEN, INSERM U1239, DC2N , Institute for Research and Innovation in Biomedicine (IRIB) , 76000 Rouen , France., Nehmé R; Institut de Chimie Organique et Analytique - ICOA UMR 7311 CNRS , Université d'Orléans , Rue de Chartres , BP6759, 45067 cedex 02 Orléans , France., Hubert-Roux M; Normandie Univ , CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014) , 76000 Rouen , France., Gandolfo P; Normandie Univ , UNIROUEN, INSERM U1239, DC2N , Institute for Research and Innovation in Biomedicine (IRIB) , 76000 Rouen , France., Castel H; Normandie Univ , UNIROUEN, INSERM U1239, DC2N , Institute for Research and Innovation in Biomedicine (IRIB) , 76000 Rouen , France., Schuler M; Institut de Chimie Organique et Analytique - ICOA UMR 7311 CNRS , Université d'Orléans , Rue de Chartres , BP6759, 45067 cedex 02 Orléans , France., Tatibouët A; Institut de Chimie Organique et Analytique - ICOA UMR 7311 CNRS , Université d'Orléans , Rue de Chartres , BP6759, 45067 cedex 02 Orléans , France., Sabot C; Normandie Univ , CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014) , 76000 Rouen , France., Renard PY; Normandie Univ , CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014) , 76000 Rouen , France.
Jazyk: angličtina
Zdroj: Bioconjugate chemistry [Bioconjug Chem] 2019 May 15; Vol. 30 (5), pp. 1385-1394. Date of Electronic Publication: 2019 Apr 16.
DOI: 10.1021/acs.bioconjchem.9b00153
Abstrakt: Fluorescein isothiocyanate (FITC) is one of the most extensively used fluorescent probes for the labeling of biomolecules. The isothiocyanate function reacts with lysine residues of proteins to provide a chemically stable thiourea linkage without releasing any byproduct. However, diversification of isothiocyanate-based reagents is still hampered by the lack of mild conditions to generate isothiocyanate chemical functions, as well as by their poor stability and limited solutions available to increase water solubility, restricting the use of isothiocyanate labeling to highly water-soluble fluorophores. Inspired by plant biological processes, we report a safe and biocompatible myrosinase-assisted in situ formation of isothiocyanate conjugates from a highly water-soluble and stable glucosinolate precursor. This method was applied for the fluorescence labeling of a plasmatic protein and fluorescence imaging of living cells.
Databáze: MEDLINE
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