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

Division of Immunology, Immunity to Infection and Respiratory Medicine

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	1430-4
Number of pages	5
Journal	Bioconjugate Chemistry
Volume	27
Issue number	6
DOIs	https://doi.org/10.1021/acs.bioconjchem.6b00245
Publication status	Published - 15 Jun 2016

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Journal Article

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10.1021/acs.bioconjchem.6b00245

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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.",

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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",

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

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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 - 2016/6/15

Y1 - 2016/6/15

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.

KW - Journal Article

U2 - 10.1021/acs.bioconjchem.6b00245

DO - 10.1021/acs.bioconjchem.6b00245

M3 - Article

C2 - 27248580

SN - 1043-1802

VL - 27

SP - 1430

EP - 1434

JO - Bioconjugate Chemistry

JF - Bioconjugate Chemistry

IS - 6

ER -

Electrophilic, Activation-Free Fluorogenic Reagent for Labeling Bioactive Amines

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