Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines.

TitleElectrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines.
Publication TypeJournal Article
Year of Publication2016
AuthorsSintes, M, De Moliner, F, Caballero-Lima, D, Denning, DW, Read, ND, Kielland, N, Vendrell, M, Lavilla, R
JournalBioconjug Chem
Volume27
Issue6
Pagination1430-4
Date Published2016 Jun 15
ISSN1520-4812
Abstract

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.

DOI10.1021/acs.bioconjchem.6b00245
Alternate JournalBioconjug. Chem.
PubMed ID27248580