Exponential Molecular Amplification by H2 O2 -Mediated Autocatalytic Deprotection of Boronic Ester Probes to Redox Cyclers

Chemistry : a European Journal
Justine PalluBenoît Limoges

Abstract

Herein, a new molecular autocatalytic reaction scheme based on a H2 O2 -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 H2 O2 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,...Continue Reading

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Citations

Sep 6, 2020·International Journal of Molecular Sciences·Gengqi LiuYumiao Zhang
May 27, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mathieu BrancaFrançois Mavré
Jul 22, 2021·Journal of the American Chemical Society·Seunghyeon KimHadley D Sikes
Oct 15, 2021·Chemical Communications : Chem Comm·Pan HuiFrançois Mavré

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