title: Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines.
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.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona , Barcelona Science Park, Baldiri Reixac 10-12, 08020 Barcelona, Spain.
authors.forename: Miquel
authors.initials: M
authors.lastname: Sintes
authors.affiliation: MRC/UoE Centre for Inflammation Research, University of Edinburgh , 47 Little France Crescent, EH16 4TJ Edinburgh, United Kingdom.
authors.forename: Fabio
authors.initials: F
authors.lastname: De Moliner
authors.affiliation: Manchester Fungal Infection Group, Institute of Inflammation and Repair, University of Manchester , CTF Building, Grafton Street, M13 9NT Manchester, United Kingdom.
authors.forename: David
authors.initials: D
authors.lastname: Caballero-Lima
authors.affiliation: Manchester Fungal Infection Group, Institute of Inflammation and Repair, University of Manchester , CTF Building, Grafton Street, M13 9NT Manchester, United Kingdom.
authors.forename: David W
authors.initials: DW
authors.lastname: Denning
authors.affiliation: Manchester Fungal Infection Group, Institute of Inflammation and Repair, University of Manchester , CTF Building, Grafton Street, M13 9NT Manchester, United Kingdom.
authors.forename: Nick D
authors.initials: ND
authors.lastname: Read
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona , Barcelona Science Park, Baldiri Reixac 10-12, 08020 Barcelona, Spain.
authors.forename: Nicola
authors.initials: N
authors.lastname: Kielland
authors.affiliation: MRC/UoE Centre for Inflammation Research, University of Edinburgh , 47 Little France Crescent, EH16 4TJ Edinburgh, United Kingdom.
authors.forename: Marc
authors.initials: M
authors.lastname: Vendrell
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona , Barcelona Science Park, Baldiri Reixac 10-12, 08020 Barcelona, Spain.|CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine , Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain.
authors.forename: Rodolfo
authors.initials: R
authors.lastname: Lavilla
mesh_terms: D000588:Amines / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D004583:Electrons; D005456:Fluorescent Dyes / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry; D005658:Fungi / Q000166:cytology; D010866:Natamycin / Q000737:chemistry; D061848:Optical Imaging; D012995:Solubility; D013194:Staining and Labeling; D014867:Water / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000588:Amines; D001896:Boron Compounds; D005456:Fluorescent Dyes; D014867:Water; D010866:Natamycin; D005459:Fluorides