A BODIPY fluorescence probe modulated by selenoxide spirocyclization reaction for peroxynitrite detection and imaging in living cells

We present the synthesis, spectroscopic properties, and live-cell application of a new BODIPY (boron dipyrromethene) fluorescence probe BOD-Se based on selenoxide spirocyclization reaction for peroxynitrite detection. The probe employs BODIPY dye as fluorophore, and is integrated with a chemical peroxynitrite responsive organoselenium functional group. By using reactive diaryl selenide and modulating by intramolecular charge-transfer (ICT) process, the probe is employed for evaluating intracellular peroxynitrite level changes. Different intracellular peroxynitrite levels can be detected with BOD-Se by confocal microscopy experiments using mouse macrophage cell line RAW264.7.

► A new fluorescence probe BOD-Se was synthesized. ► The probe could detect peroxynitrite based on selenoxide spirocyclization reaction. ► The detection mechanism was modulated via intramolecular charge transfer (ICT) process. ► Confocal microscopy imaging confirm the probe can evaluate intracellular ONOO− level changes.