Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines

Miquel Sintes, Fabio De Moliner, David Caballero-Lima, David W Denning, Nick D Read, Nicola Kielland, Marc Vendrell, Rodolfo Lavilla

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
JournalBioconjugate chemistry
DOIs
Publication statusPublished - 1 Jun 2016

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