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Biosensors 2017, 7(3), 36; doi:10.3390/bios7030036

A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione

1
ARC Centre of Excellence for Nanoscale BioPhotonics, Institute of Photonics and Advanced Sensing, Department of Chemistry, School of Physical Sciences, The University of Adelaide, Adelaide SA 5005, Australia
2
Discipline of Physiology, Faculty of Health Sciences, The University of Adelaide, Adelaide SA 5005, Australia
*
Authors to whom correspondence should be addressed.
Received: 11 August 2017 / Revised: 24 August 2017 / Accepted: 4 September 2017 / Published: 6 September 2017
(This article belongs to the Special Issue Nanomaterials Based Optical Biosensors)
View Full-Text   |   Download PDF [3009 KB, uploaded 6 September 2017]   |  

Abstract

γ-Glutamyl-cysteinyl-glycine (GSH) plays a critical role in maintaining redox homeostasis in biological systems and a decrease in its cellular levels is associated with diseases. Existing fluorescence-based chemosensors for GSH acts as irreversible reaction-based probes that exhibit a maximum fluorescence (‘turn-on’) once the reaction is complete, regardless of the actual concentration of GSH. A reversible, reaction-based ‘turn-off’ probe (1) is reported here to sense the decreasing levels of GSH, a situation known to occur at the onset of various diseases. The more fluorescent merocyanine (MC) isomer of 1 exists in aqueous solution and this reacts with GSH to induce formation of the ring-closed spiropyran (SP) isomer, with a measurable decrease in absorbance and fluorescence (‘turn-off’). Sensor 1 has good aqueous solubility and shows an excellent selectivity for GSH over other biologically relevant metal ions and aminothiol analytes. The sensor permeates HEK 293 cells and an increase in fluorescence is observed on adding buthionine sulfoximine, an inhibitor of GSH synthesis. View Full-Text
Keywords: reversible sensor; photoswitch; spiropyran; fluorescent sensor; reduced glutathione; intracellular sensing; turn-off sensor reversible sensor; photoswitch; spiropyran; fluorescent sensor; reduced glutathione; intracellular sensing; turn-off sensor
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Heng, S.; Zhang, X.; Pei, J.; Abell, A.D. A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione. Biosensors 2017, 7, 36.

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