Abstract
Peroxynitrite (ONOO−), an essential reactive oxygen species, plays a critical role in various cellular processes. However, irregular ONOO− concentration will disturb the normal function of cells. In this work, we present the design and synthesis of a new peroxynitrite probe, BTNB, in which 3-benzyl-2-(6-hydroxylnaphthalene-2-vinyl) benzothiazolium bromide as the signaling fluorophore was integrated with benzyl borate moiety as the responsive group. The faint electron-withdrawing nature of the boronic ester caused a reduction in the intramolecular charge transfer (ICT) character of BTNB, which was greatly enhanced by ONOO− due to the oxidation of aryl boronates to yield a phenolic product. As a result, BTNB exhibited ratiometric responses to ONOO− with high selectivity and sensitivity (LOD = 0.25 μM) in an aqueous solution. Having large stokes shift (163 nm), good mitochondrial targeting ability and low cytotoxicity, the probe BTNB exhibits good performance in dual-channel (yellow and red channel) ratiometric imaging of ONOO− in cells, zebrafish, and Malpighian tubes.
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