A selective phosphine-based fluorescent probe for nitroxyl in living cells.

A novel fluorescein-based fluorescent probe for nitroxyl (HNO) based on the reductive Staudinger ligation of HNO with an aromatic phosphine was prepared. This probe reacts with HNO derived from Angeli's salt and 4-bromo Piloty's acid under physiological conditions without interference by other biological redox species. Confocal microscopy demonstrates this probe detects HNO by fluorescence in HeLa cells and mass spectrometric analysis of cell lysates confirms this probe detects HNO following the proposed mechanism.