A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione

doi:10.11944/j.issn.1000-0518.2020.07.200025

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (7): 847-854.DOI: 10.11944/j.issn.1000-0518.2020.07.200025

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A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione

ZHANG Chenglu^*, SUN Yuedong, DING Yanwei, WANG Jing, LIU Xingbing, WANG Nan, SONG Fulu

College of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China

Published:2020-07-01 Online:2020-07-07
Contact: ZHANG Chenglu, professor; Tel:0411-82158329; E-mail:zhangchenglu@lnnu.edu.cn; Research interests:design and synthesis of bioactive molecules and fluorescent probes
Supported by:
Supported by the Science and Technology Project of Liaoning Education Department(No.2009A426)

Abstract

Abstract: In order to recognize small-molecule biothiols selectively, quinolinone was used as a fluorophore. Since thiol molecules can easily break the Se—N bond, a new fluorescent probe (E)-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)-3-(5-((4-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)phenyl)thio)-1,3,4-oxadiazol-2-yl)acrylamide (MNQ) was designed and synthesized by splicing quinolinone (E)-3-(5-mercapto-1,3,4-oxadiazol-2-yl)-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)acrylamide (MQ5) with ebselen 2-(4-bromophenyl)benzo[d][1,2]selenazol-3(2H)-one (SQ6). The structure was characterized by infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR) and high-resolution mass spectrometry (HRMS), and its fluorescence properties were explored by fluorescence spectroscopy. The result shows that MNQ has obvious fluorescence quenching ability for glutathione (GSH). When other amino acids exist, the probe has good anti-interference ability, and can be used as a fluorescence quenching probe for identifying and detecting GSH. The detection limit is 2.99×10^-7 mol/L, and the response time can be as low as 35 s. It has potential application as a fluorescent probe for detecting GSH.

Key words: quinolinone, fluorescence recognition, glutathione, ebselen

ZHANG Chenglu, SUN Yuedong, DING Yanwei, WANG Jing, LIU Xingbing, WANG Nan, SONG Fulu. A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione[J]. Chinese Journal of Applied Chemistry, 2020, 37(7): 847-854.

References

[1] Liu Y,Lv X,Liu J,et al. Construction of a Selective Fluorescent Probe for GSH Based on a Chloro-Functionalized Coumarin-enone Dye Platform[J]. Chem-Eur J,2015,21(12):4747-4754.
[2] Zhang S,Ong C N,Shen H M. Critical Roles of Intracellular Thiols and Calcium in Parthenolide-Induced Apoptosis in Human Colorectal Cancer Cells[J]. Cancer Lett,2004,208(2):0-153.
[3] Kristine S J,Rosa E H,Jakob R W. Kinetic and Thermodynamic Aspects of Cellular Thiol Disulfide Redox Regulation[J]. Antioxid Redox Sign,2009,11(5):1047-1058.
[4] Tang B,Yin L,Wang X,et al. A Fast-Response, Highly Sensitive and Specific Organoselenium Fluorescent Probe For Thiols and Its Application in Bioimaging[J]. Chem Commun,2009,35:5293-5295.
[5] Ng C F,Schafer F Q,Buettner G R,et al. The Rate of Cellular Hydrogen Peroxide Removal Shows Dependency on GSH:Mathematical Insight into in Vivo H₂O₂ and GPx Concentrations[J]. Free Radical Res Commun,2007,41(11):1201-1211.
[6] Anna S C,Sandra G F,Hans S,et al. A Standardized Protocol for Comparable Analysis of GSH/GSSG by UHPLC-ESI-MSMS for Human Plasma[J]. J Chromatogr B,2019,1104:67-72.
[7] Song Y L,Li J,Zhou X,et al. Recent Progress on the Development of Glutathione (GSH) Selective Fluorescent and Colorimetric Probes[J]. Coordin Chem Rev,2018,366:29-68.
[8] Hong J A,Kim M J,Eo J,et al. A Turn-On Fluorescent Probe for Live-Cell Imaging of Biothiols[J]. Bull Korean Chem Soc,2018,39(4):425-426.
[9] Jennifer K N,Prithy R,Toshiro M,et al. In Vitro and ex Vivo Uptake of Glutathione(GSH) Across the Intestinal Epithelium and Fate of Oral GSH after in Vivo Supplementation[J]. J Agric Food Chem,2014,62(39):9499-9506.
[10] Ivanov A R,Nazimov I V,Baratova L A. Qualitative and Quantitative Determination of Biologically Active Low-Molecular-Mass Thiols in Human Blood by Reversed-Phase High-Performance Liquid Chromatography with Photometry and Fluorescence Detection[J]. J Chromatogr A,2000,895(1):167-171.
[11] Chen G,Zhang L,Wang J. Miniaturized Capillary Electrophoresis System with a Carbon Nanotube Microelectrode for Rapid Separation and Detection of Thiols[J]. Talanta,2004,64(4):1018-1023.
[12] Narang J,Chauhan N,Jain P,et al. Silver Nanoparticles/Multiwalled Carbon Nanotube/Polyaniline Film for Amperometric Glutathione Biosensor[J]. Int J Biolog Macromol,2012,50(3):672-678.
[13] Yoshida M,Kamiya M,Yamasoba T,et al. A Highly Sensitive, Cell-Membrane-Permeable Fluorescent Probe for Glutathione[J]. Bioorg Med Chem Lett,2014,24(18):4363-4366
[14] Jhong Y,Hsieh W H,Chir J L,et al. A Highly Selective and Turn-on Fluorescence Sensor for Detection of Cyanide[J]. J Fluoresc,2014,24(6):1723-1726.
[15] Liu X,Li T,Wu Q,et al. Carbon Nanodots as a Fluorescence Sensor for Rapid and Sensitive Detection of Cr(Ⅵ) and Their Multifunctional Applications[J]. Talanta,2017,165:216-222.
[16] Zheng S L,Liu J W,Wu Y Y,et al. Small-Molecule Inhibitors of Wnt Signaling Pathway: Towards Novel Anticancer Therapeutics[J]. Future Med Chem,2015,7(18):2485-2505.
[17] Wang H Z,Xiao M J,Zhang J Q,et al. Studies on the Synthesis and Properties of Quinolinone-Based Fluorescent Probe[J]. Acta Sci Nat Univ Sunyatseni,2014,53(2):94-100.
[18] Wu L J,Yang Y,Song R J,et al. An Access to 1,3-Azasiline-Fused Quinolinones via Oxidative Heteroannulation Involving Silyl C(sp³)—H Functionalization[J]. Chem Commun,2018,54(21):1367-1370..
[19] Gao Z,Han B,Chen K,et al. A Novel Single-Fluorophore-Based Ratiometric Fluorescent Probe for Direct Detection of Isocyanates in Air[J]. Chem Commun,2017,53(46):6231-6234.
[20] Pires M M,Chmielewski J. Fluorescence Imaging of Cellular Glutathione Using a Latent Rhodamine[J]. Org Lett,2008,10(5):837-840.
[21] Lee J H,Lim C S,Tian Y S,et al. A Two-Photon Fluorescent Probe for Thiols in Live Cells and Tissues[J]. J Am Chem Soc,2010,132(4):1216-1217.
[22] LIU Yawei. Construction of Carbon Heterobonds and Their Application in the Synthesis of Sulfide and Quinazoline Derivatives[D]. Zhengzhou:Henan University,2018(in Chinese).
刘亚威. 碳杂键的构建及其在硫醚和喹唑啉衍生物合成中的应用[D]. 郑州:河南大学,2018.
[23] WANG Huizhen. Synthesis and Properties of Quinolinone Fluorescent Probes.Mianyang[D]. Mianyang:Southwest University of Science and Technology,2014(in Chinese).
王会镇. 喹啉酮荧光探针的合成及性能研究[D]. 绵阳: 西南科技大学,2014.
[24] YAN Xueming, ZHANG Hongying, ZENG Xiong. Study on Synthesis of Novel Ebselen Analogs[J]. J Univ South China(Sci Technol),2006,20(3):88-90(in Chinese).
颜雪明,张红英,曾雄. 新型Ebselen类似物的合成研究[J]. 南华大学学报(自然科学版),2006,20(3):88-90.
[25] YAN Xueming,LU Zhiqiang,YANG Pengfei. Study on the Synthesis of 2-Phenyl-1,2-Benzoisoselazol-3-(2H)-one[J]. Fine Chem Intermed,2005,35(4):22-27(in Chinese).
颜雪明,卢志强,阳鹏飞. 2-苯基-1,2-苯并异硒唑-3-(2H)-酮的合成研究[J]. 精细化工中间体,2005,35(4):22-27.
[26] Krishna P B,Govindasamy M. Synthesis, Characterization, and Antioxidant Activity of Some Ebselen Analogues[J]. Chem-Eur J,2007,13:4594-4601.
[27] Samanta S,Goswami S,Ramesh A,et al. A New Fluorogenic Probe for Solution and Intra-Cellular Sensing of Trivalent Cations in Model Human Cells[J]. Sens Actuators B,2014,194:120-126.
[28] Mugesh G,Sarma B K. Glutathione Peroxidase(GPx)-like Antioxidant Activity of the Organoselenium Drug Ebselen:Unexpected Complications with Thiol Exchange Reactions[J]. J Am Chem Soc,2005,127(32):11477-11485.

A Quinolinone-Based Fluorescent Probe for Rapid and Highly Selective Detection of Glutathione

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