The development of a novel AND logic based fluorescence probe for the detection of peroxynitrite and GSH

Abstract

We have developed a novel AND logic based fluorescence probe for the simultaneous detection of ONOO^- and GSH (<b>GSH-PF3</b>). The <b>GSH-PF3</b> probe was synthesised over three steps starting from commercially available fluorescein. The probe was constructed by attaching the GSH reactive motif, 2,4-dinitrobenzenesulfonyl, to the previously reported boronate fluorescence based probe, <b>PF3</b>. <b>GSH-PF3</b> produced only a small fluorescence response towards the addition of GSH or ONOO^- separately. However, when the probe was exposed to both analytes, there was a significant (40-fold) fluorescence enhancement. <b>GSH-PF3</b> demonstrated an excellent selectivity towards both GSH and ONOO^-. In cellular imaging experiments the probe was shown to be cell permeable with no 'turn-on' response observed for the addition of either GSH or ONOO^- separately. However, in the presence of both analytes, a clear fluorescence response was observed in live cells. <b>GSH-PF3</b> was further able to monitor the co-existence of metabolically produced ONOO^- and GSH by exogenous stimulation.