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

• Published in: Chemical science (Cambridge) Vol. 9; no. 15; pp. 3672 - 3676
• Main Authors: Sedgwick, Adam C., Han, Hai-Hao, Gardiner, Jordan E., Bull, Steven D., He, Xiao-Peng, James, Tony D.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.04.2018; Royal Society of Chemistry
• Subjects: Bile; Chemistry; Chemistry, Multidisciplinary; Fluorescein; Fluorescent indicators; Physical Sciences; Science & Technology; OXIDATIVE STRESS; METABOLISM; GLUTATHIONE; STRATEGY; IN-VIVO; DISEASE; NITRIC-OXIDE; HYDROGEN-PEROXIDE; CANCER; LIVING CELLS
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/C8SC00733K

We have developed a novel AND logic based fluorescence probe for the simultaneous detection of ONOO − and GSH ( GSH-PF3 ). The GSH-PF3 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, PF3 . GSH-PF3 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. GSH-PF3 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. GSH-PF3 was further able to monitor the co-existence of metabolically produced ONOO − and GSH by exogenous stimulation.