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

doi:10.1021/acs.bioconjchem.6b00245

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 journal › Article › peer-review

Abstract / Description of output

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 language	English
Journal	Bioconjugate chemistry
DOIs	https://doi.org/10.1021/acs.bioconjchem.6b00245
Publication status	Published - 1 Jun 2016

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10.1021/acs.bioconjchem.6b00245

2016-BioconjugateChem-Vendrell
Author's peer-reviewed manuscript as accepted for publication
Accepted author manuscript, 311 KBLicence: Creative Commons: Attribution (CC-BY)

Development of phloem-mobile xenobiotics with enhanced transport properties
Oparka, K.
UK industry, commerce and public corporations
1/09/15 → 30/06/19
Project: Research
ENDOIMAGE - Activatable Fluorescent Probes as Smart Diagnostic Tools for Microendoscopy Imaging
Vendrell Escobar, M.
EU other
1/08/13 → 31/07/17
Project: Research

Cite this

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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.",

author = "Miquel Sintes and {De Moliner}, Fabio and David Caballero-Lima and Denning, {David W} and Read, {Nick D} and Nicola Kielland and Marc Vendrell and Rodolfo Lavilla",

year = "2016",

month = jun,

day = "1",

doi = "10.1021/acs.bioconjchem.6b00245",

language = "English",

journal = "Bioconjugate chemistry",

issn = "1043-1802",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines

AU - Sintes, Miquel

AU - De Moliner, Fabio

AU - Caballero-Lima, David

AU - Denning, David W

AU - Read, Nick D

AU - Kielland, Nicola

AU - Vendrell, Marc

AU - Lavilla, Rodolfo

PY - 2016/6/1

Y1 - 2016/6/1

N2 - 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.

AB - 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.

U2 - 10.1021/acs.bioconjchem.6b00245

DO - 10.1021/acs.bioconjchem.6b00245

M3 - Article

C2 - 27248580

SN - 1043-1802

JO - Bioconjugate chemistry

JF - Bioconjugate chemistry

ER -

Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines

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Projects

Development of phloem-mobile xenobiotics with enhanced transport properties

ENDOIMAGE - Activatable Fluorescent Probes as Smart Diagnostic Tools for Microendoscopy Imaging

Cite this