A Rationally Designed Reversible ‘Turn-Off’ Sensor for Glutathione
Open Access
- 6 September 2017
- journal article
- research article
- Published by MDPI AG in Biosensors
- Vol. 7 (3), 36
- https://doi.org/10.3390/bios7030036
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.Keywords
Funding Information
- Australian Research Council (CE140100 003)
This publication has 48 references indexed in Scilit:
- Gas chromatographic–mass spectrometric analysis of the tripeptide glutathione in the electron-capture negative-ion chemical ionization modeAmino Acids, 2015
- Glutathione during embryonic developmentBiochimica et Biophysica Acta (BBA) - General Subjects, 2014
- Glutathione and modulation of cell apoptosisBiochimica et Biophysica Acta (BBA) - Molecular Cell Research, 2012
- Methods for the Determination of Plasma or Tissue Glutathione LevelsPublished by Springer Science and Business Media LLC ,2012
- Electrochemical determination of glutathione: a reviewThe Analyst, 2012
- Cell signalling and the glutathione redox systemBiochemical Pharmacology, 2002
- Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione coupleFree Radical Biology & Medicine, 2001
- Glutathione: an overview of biosynthesis and modulationChemico-Biological Interactions, 1998
- Compartmentation of Glutathione: Implications for the Study of Toxicity and DiseaseToxicology and Applied Pharmacology, 1996
- GLUTATHIONEAnnual Review of Biochemistry, 1983