Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines

Bioconjug Chem. 2016 Jun 15;27(6):1430-4. doi: 10.1021/acs.bioconjchem.6b00245. Epub 2016 Jun 6.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Boron Compounds / chemistry*
  • Electrons*
  • Fluorescent Dyes / chemistry*
  • Fluorides / chemistry
  • Fungi / cytology
  • Natamycin / chemistry
  • Optical Imaging
  • Solubility
  • Staining and Labeling
  • Water / chemistry

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Amines
  • Boron Compounds
  • Fluorescent Dyes
  • Water
  • Natamycin
  • Fluorides