Ratiometric Detection of Glutathione Based on Disulfide Linkage Rupture Between a FRET Coumarin Donor and a Rhodamine Acceptor

Overview

Journal Chembiochem

Specialty Biochemistry

Date 2021 May 13

PMID 33983667

Citations 8

Authors

Yibin Zhang

Shuai Xia

Shulin Wan

Tessa E Steenwinkel

Tara Vohs

Rudy L Luck

Thomas Werner

Haiying Liu

Affiliations

Soon will be listed here.

Abstract

Abnormal levels of glutathione, a cellular antioxidant, can lead to a variety of diseases. We have constructed a near-infrared ratiometric fluorescent probe to detect glutathione concentrations in biological samples. The probe consists of a coumarin donor, which is connected through a disulfide-tethered linker to a rhodamine acceptor. Under the excitation of the coumarin donor at 405 nm, the probe shows weak visible fluorescence of the coumarin donor at 470 nm and strong near-infrared fluorescence of the rhodamine acceptor at 652 nm due to efficient Forster resonance energy transfer (FRET) from the donor to the acceptor. Glutathione breaks the disulfide bond through reduction, which results in a dramatic increase in coumarin fluorescence and a corresponding decrease in rhodamine fluorescence. The probe possesses excellent cell permeability, biocompatibility, and good ratiometric fluorescence responses to glutathione and cysteine with a self-calibration capability. The probe was utilized to ratiometrically visualize glutathione concentration alterations in HeLa cells and Drosophila melanogaster larvae.

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References

Chen X, Zhou Y, Peng X, Yoon J . Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev. 2010; 39(6):2120-35. DOI: 10.1039/b925092a. View

Niu L, Chen Y, Zheng H, Wu L, Tung C, Yang Q . Design strategies of fluorescent probes for selective detection among biothiols. Chem Soc Rev. 2015; 44(17):6143-60. DOI: 10.1039/c5cs00152h. View

Xia S, Wang J, Bi J, Wang X, Fang M, Phillips T . Fluorescent Probes Based on π-Conjugation Modulation between Hemicyanine and Coumarin Moieties for Ratiometric Detection of pH Changes in Live Cells with Visible and Near-infrared Channels. Sens Actuators B Chem. 2018; 265:699-708. PMC: 6178979. DOI: 10.1016/j.snb.2018.02.168. View

Jiang Q, Zhang C, Wang H, Peng T, Zhang L, Wang Y . Mitochondria-Targeting Immunogenic Cell Death Inducer Improves the Adoptive T-Cell Therapy Against Solid Tumor. Front Oncol. 2019; 9:1196. PMC: 6861368. DOI: 10.3389/fonc.2019.01196. View

Xia S, Zhang Y, Fang M, Mikesell L, Steenwinkel T, Wan S . A FRET-Based Near-Infrared Fluorescent Probe for Ratiometric Detection of Cysteine in Mitochondria. Chembiochem. 2019; 20(15):1986-1994. PMC: 6676905. DOI: 10.1002/cbic.201900071. View

Wang Y, Zhu M, Jiang E, Hua R, Na R, Li Q . A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells. Sci Rep. 2017; 7(1):4377. PMC: 5491497. DOI: 10.1038/s41598-017-03901-8. View

Giustarini D, Dalle-Donne I, Milzani A, Rossi R . Detection of glutathione in whole blood after stabilization with N-ethylmaleimide. Anal Biochem. 2011; 415(1):81-3. DOI: 10.1016/j.ab.2011.04.013. View

Yue Y, Huo F, Cheng F, Zhu X, Mafireyi T, Strongin R . Functional synthetic probes for selective targeting and multi-analyte detection and imaging. Chem Soc Rev. 2019; 48(15):4155-4177. DOI: 10.1039/c8cs01006d. View

Abdillah A, Sonawane P, Kim D, Mametov D, Shimodaira S, Park Y . Discussions of Fluorescence in Selenium Chemistry: Recently Reported Probes, Particles, and a Clearer Biological Knowledge. Molecules. 2021; 26(3). PMC: 7866183. DOI: 10.3390/molecules26030692. View

10.

Wang L, Wang J, Xia S, Wang X, Yu Y, Zhou H . A FRET-based near-infrared ratiometric fluorescent probe for detection of mitochondria biothiol. Talanta. 2020; 219:121296. DOI: 10.1016/j.talanta.2020.121296. View

11.

Zhang Y, Xia S, Fang M, Mazi W, Zeng Y, Johnston T . New near-infrared rhodamine dyes with large Stokes shifts for sensitive sensing of intracellular pH changes and fluctuations. Chem Commun (Camb). 2018; 54(55):7625-7628. PMC: 6058674. DOI: 10.1039/c8cc03520b. View

12.

Niu G, Zhang P, Liu W, Wang M, Zhang H, Wu J . Near-Infrared Probe Based on Rhodamine Derivative for Highly Sensitive and Selective Lysosomal pH Tracking. Anal Chem. 2017; 89(3):1922-1929. DOI: 10.1021/acs.analchem.6b04417. View

13.

Hanwell M, Curtis D, Lonie D, Vandermeersch T, Zurek E, Hutchison G . Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J Cheminform. 2012; 4(1):17. PMC: 3542060. DOI: 10.1186/1758-2946-4-17. View

14.

Xia S, Fang M, Wang J, Bi J, Mazi W, Zhang Y . Near-infrared fluorescent probes with BODIPY donors and rhodamine and merocyanine acceptors for ratiometric determination of lysosomal pH variance. Sens Actuators B Chem. 2019; 294:1-13. PMC: 6730546. DOI: 10.1016/j.snb.2019.05.005. View

15.

Gao P, Pan W, Li N, Tang B . Fluorescent probes for organelle-targeted bioactive species imaging. Chem Sci. 2019; 10(24):6035-6071. PMC: 6585876. DOI: 10.1039/c9sc01652j. View

16.

Martinez-Cuezva A, Lopez-Leonardo C, Bautista D, Alajarin M, Berna J . Stereocontrolled Synthesis of β-Lactams within [2]Rotaxanes: Showcasing the Chemical Consequences of the Mechanical Bond. J Am Chem Soc. 2016; 138(28):8726-9. DOI: 10.1021/jacs.6b05581. View

17.

Mulay S, Kim Y, Choi M, Lee D, Choi J, Lee Y . Enhanced Doubly Activated Dual Emission Fluorescent Probes for Selective Imaging of Glutathione or Cysteine in Living Systems. Anal Chem. 2018; 90(4):2648-2654. DOI: 10.1021/acs.analchem.7b04375. View

18.

Wang J, Xia S, Bi J, Zhang Y, Fang M, Luck R . Near-infrared fluorescent probes based on TBET and FRET rhodamine acceptors with different p values for sensitive ratiometric visualization of pH changes in live cells. J Mater Chem B. 2019; 7(2):198-209. PMC: 6668629. DOI: 10.1039/C8TB01524D. View

19.

Liu C, Wu T, Liu C, Lin S . Live-cell imaging of biothiols via thiol/disulfide exchange to trigger the photoinduced electron transfer of gold-nanodot sensor. Anal Chim Acta. 2014; 849:57-63. DOI: 10.1016/j.aca.2014.08.022. View

20.

Yuan L, Lin W, Zheng K, Zhu S . FRET-based small-molecule fluorescent probes: rational design and bioimaging applications. Acc Chem Res. 2013; 46(7):1462-73. DOI: 10.1021/ar300273v. View