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  3. Tandem Payne/Dakin Reaction: A New Strategy for Hydrogen Peroxide Detection and Molecular Imaging

Tandem Payne/Dakin Reaction: A New Strategy for Hydrogen Peroxide Detection and Molecular Imaging

  • Angew Chem Int Ed Engl. 2018 Aug 6;57(32):10173-10177. doi: 10.1002/anie.201805162.
Sen Ye 1,  Jun Jacob Hu 1,  Dan Yang 1
Affiliations

Affiliation

  • 1 Morningside Laboratory for Chemical Biology and Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China.
PMID: 29932292 DOI: 10.1002/anie.201805162
Abstract

Hydrogen peroxide (H2 O2 ) has been recognized as one of the most significant ROS (Reactive Oxygen Species) in human health and disease. Because of the intrinsic attributes of H2 O2 -such as its low reactivity under physiological pH-it is exceedingly challenging to develop small-molecule fluorescent probes with high selectivity and sensitivity for visualization of H2 O2 in an intricate biological milieu. To address this gap, a rationally designed tandem Payne/Dakin reaction is reported that is specific to molecular recognition of H2 O2 . New H2 O2 probes based on this unique chemical strategy can be easily synthesized by a general coupling reaction, and the practical applicability of those probes has been confirmed by the visualization of endogenously produced H2 O2 in living cells. In particular, starvation-induced H2 O2 production in mouse macrophages has been detected by the novel probe in both confocal imaging and flow cytometry. This tandem Payne/Dakin reaction provides a basis for developing more sophisticated molecular tools to interrogate H2 O2 functions in biological phenomena.

Keywords

autophagy; fluorescent probes; hydrogen peroxide; reactive oxygen species; redox signaling.

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