Dual-Site Fluorescent Probe to Monitor Intracellular Nitroxyl and GSH-GSSG Oscillations.

Nitroxyl (HNO), the one-electron-reduction product of NO has recently been revealed to have potentially beneficial pharmacological properties in cardiovascular health as a result of interactions with specific thiols such as glutathione (GSH). To disentangle the complicated inter-relationship between HNO and GSH in the signal transduction and oxidative pathways, we designed and synthesized a dual-site fluorescent probe NCF to indicate cellular HNO and GSH-GSSG balance. The sensitive and selective detection of HNO was achieved by incorporating an organophosphine group to naphthaldehyde-TCF. Then the resulted fluorescent product is able to monitor the conversion of GSH and GSSG reversibly. Additionally, outstanding biocompatibility make it capable of monitoring intracellular HNO and consequently GSH-GSSG oscillationsin living cells. We anticipate that NCF will be a unique molecular tool to investigate the interplaying roles of HNO and GSH.