Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines

Herein we report the preparation of BODIPY mesoionic acid fluorides through a short sequence involving an isocyanide multicomponent reaction as the key synthetic step. These novel BODIPY acid fluorides are water-stable electrophilic reagents that can be used for the fluorescent derivatization of ami...

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Bibliographic Details
Published in:Bioconjugate chemistry 2016-06, Vol.27 (6), p.1430-1434
Main Authors: Sintes, Miquel, De Moliner, Fabio, Caballero-Lima, David, Denning, David W, Read, Nick D, Kielland, Nicola, Vendrell, Marc, Lavilla, Rodolfo
Format: Article
Language:English
Subjects:
Amines - chemistry
Antimicrobial agents
Boron Compounds - chemistry
Chemical reactions
Electrons
Fluorescence
Fluorescent Dyes - chemistry
Fluorides - chemistry
Fungi
Fungi - cytology
Molecules
Natamycin - chemistry
Optical Imaging
Organic chemicals
Solubility
Staining and Labeling
Water - chemistry
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Summary:Herein we report the preparation of BODIPY mesoionic acid fluorides through a short sequence involving an isocyanide multicomponent reaction as the key synthetic step. These novel BODIPY acid fluorides are water-stable electrophilic reagents that can be used for the fluorescent derivatization of amine-containing biomolecules using mild and activation-free reaction conditions. As a proof of principle, we have labeled the antifungal natamycin and generated a novel fluorogenic probe for imaging a variety of human and plant fungal pathogens, with excellent selectivity over bacterial cells.
ISSN:1043-1802
1520-4812
DOI:10.1021/acs.bioconjchem.6b00245