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Laboratoire d'Electrochimie Moleculaire, LEM, Paris

UMR CNRS - Université Paris Diderot - Paris France

Master Frontiers in Chemistry | UFR de Chimie - Université Paris Diderot - Paris 7 CNRS - Institut de chimie Université de Paris Master Chimie Sorbonne Paris Cité UFR de Chimie - Université Paris Diderot - Paris 7 CNRS - Institut de chimie
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Université Paris Diderot
Université de Paris CNRS, Centre National de la Recherche Scientifique

Le LEM - Publications: Abstracts

Publication 880

Chem.-Eur. J., 25 (31), 7534-7546, 2019


Exponential Molecular Amplification by H2O2-mediated Autocatalytic Deprotection of Boronic Ester Probes to Redox Cyclers

Justine Pallu, Charlie Rabin, Geordie Creste, Mathieu Branca, François Mavré, and Benoit Limoges

Laboratoire d'Electrochimie Moléculaire, UMR CNRS 7591, Université Paris Diderot, Sorbonne Paris Cité, 15 Rue Jean-Antoine de Baïf, F-75205, Paris Cedex 13, France

Herein, a new molecular autocatalytic reaction scheme based on a H2O2‐mediated deprotection of a boronate ester probe into a redox cycling compound is described, generating an exponential signal gain in the presence of O2 and a reducing agent or enzyme. For such a purpose, new chemosensing probes built around a naphthoquinone/naphthohydroquinone redox‐active core, masked by a self‐immolative boronic ester protecting group, were designed. With these probes, typical autocatalytic kinetic traces with characteristic lags and exponential phases were obtained by using either UV/Visible or fluorescence optical detection, or by using electrochemical monitoring. Detection of concentrations as low as 0.5 μm H2O2 and 0.5 nm of a naphthoquinone derivative were achieved in a relatively short time (<1 h). From kinetic analysis of the two cross‐activated catalytic loops associated with the autocatalysis, the key parameters governing the autocatalytic reaction network were determined, indirectly showing that the analytical performances are currently limited by the slow nonspecific self‐deprotection of boronate probes. Collectively, the present results demonstrate the potential of this new exponential molecular amplification strategy, which, owing to its generic nature and modularity, is quite promising for coupling to a wide range of bioassays involving H2O2 or redox cycling compounds, or for use as a new building block in the development of more complex chemical reaction networks.

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