Citation: Linfang ZHANG, Wenzhu YIN, Gui YIN. A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells[J]. Chinese Journal of Inorganic Chemistry, ;2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405 shu

A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells

Linfang ZHANG ¹ ,
Wenzhu YIN ² ,
Gui YIN ^{1, 3,,}

1.
School of Chemistry and Chemical Engineering, Yili Normal University, Yining, Xinjiang 835000, China
2.
Institute of Veterinary Immunology & Engineering, National Research Center of Engineering and Technology for Veterinary Biologicals, Jiangsu Academy of Agricultural Sciences, Nanjing 210014, China
3.
State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

Corresponding author: Gui YIN, yingui@nju.edu.cn
Received Date: 12 November 2024
Revised Date: 16 December 2024

Figures(9)

Using 2-dicyanomethylene-3-cyano-4, 5, 5-trimethyl-2, 5-dihydrofuran (TCF) as a near-infrared fluorescent chromophore, we designed and synthesized a TCF-based fluorescent probe TCF-NS by introducing 2, 4-dinitrophenyl ether as the recognized site for H₂S. The probe TCF-NS displayed a rapid-response fluorescent against H₂S with high sensitivity and selection but had no significant fluorescence response to other biothiols. Furthermore, TCF-NS was applied to sense H₂S in living cells successfully with minimized cytotoxicity and a large Stokes shift.
- hydrogen sulfide,
- near-infrared fluorescence probe,
- cell imaging
1. [1]
  WANG L Y, ZHANG C F, TANG H, CAO D R. A novel chromophore reaction-based pyrrolopyrrole aza-BODIPY fluorescent probe for H₂S detection and its application in food spoilage[J]. Food Chem., 2023,427136591. doi: 10.1016/j.foodchem.2023.136591
2. [2]
  GONG S Y, ZHENG Z P, GUAN X G, FENG S, FENG X G, FENG S M, FENG G Q. Near-infrared mitochondria-targetable fluorescent probe for high-contrast bioimaging of H₂S[J]. Anal. Chem., 2021,93(14):5700-5708. doi: 10.1021/acs.analchem.0c04639
3. [3]
  RAJALAKSHMI K, MUTHUSAMY S, LEE H J, KANNAN P, ZHU D W, SONG J W, NAM Y S, HEO D N, KWON I, LUO Z B, XU Y G. Dual-channel fluorescent probe for discriminative detection of H₂S and N₂H₄: Exploring sensing mechanism and real-time applications[J]. J. Hazard. Mater., 2024,465133036. doi: 10.1016/j.jhazmat.2023.133036
4. [4]
  CHEN S T, LIU T, YUAN X M, ZHOU L Y. Construction of an effective near-infrared fluorescence "turn-on" probe for hydrogen sulfide detection and imaging in living inflammatory cell and zebrafish models[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2024,323124863. doi: 10.1016/j.saa.2024.124863
5. [5]
  SHANG H Y, DONG X, ZHANG X F, ZHANG A P, DU J W. Electrocatalytic-induced electrochemical sensor based on the heterojunction Cu-Ni/Ni(OH)₂ for the detection of hydrogen sulfide[J]. ACS Appl. Nano Mater., 2023,6(24):23576-23584. doi: 10.1021/acsanm.3c05075
6. [6]
  ZHANG H L, LI S Y, ZHENG H P, HAN Z Z, LIN B, WANG Y Y, GUO X J, ZHOU T G, ZHANG H B, WU J J, ZHANG H, TANG J L. A visual color response test paper for the detection of hydrogen sulfide gas in the air[J]. Molecules, 2023,28(13)5044. doi: 10.3390/molecules28135044
7. [7]
  XIAO X, SHEN Y Z, ZHOU X, SUN B G, WANG Y, CAO J X. Innovative nanotechnology-driven fluorescence assays for reporting hydrogen sulfide in food-related matrices[J]. Coord. Chem. Rev., 2023,480215012. doi: 10.1016/j.ccr.2023.215012
8. [8]
  BU D D, WANG Y Y, WU N, FENG W, WEI D H, LI Z X, YU M M. A mitochondrial-targeted ratiometric probe for detecting intracellular H₂S with high photostability[J]. Chin. Chem. Lett., 2021,32(5):1799-1802. doi: 10.1016/j.cclet.2020.12.044
9. [9]
  HUANG J J, ZOU X R, LIU X E, RAN H Y, PANG M L, ZHAO L L, WANG P, CHEN J, CHEN M Z, PENG Y B. Construction of a highly specific fluorescence "turn-on" probe for H₂S detection and imaging in drug-induced live cells, zebrafish and mice arthritis models[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2024,323124928. doi: 10.1016/j.saa.2024.124928
10. [10]
  CAI W J, XIN T, TU Y Y, SUN L L, LIAO G M, LIU G, FAN C B. A near-infrared turn-on fluorescent probe for the detection of hydrogen sulfide in water samples and food spoilage[J]. Anal. Chim. Acta, 2024,1320342992. doi: 10.1016/j.aca.2024.342992
11. [11]
  YANG Y X, CHEN L, HU X L, ZHONG K L, LI S D, YAN X M, ZHANG J L, TANG L J. Synthesis of a turn-on fluorescent probe for hydrogen sulfide and its application in red wine and living cells[J]. Chin. J. Org. Chem., 2023,43(1):308-312. doi: 10.6023/cjoc202207011
12. [12]
  ZHAO X J, JIANG Y R, LI Y T, YANG B Q, LIU C, LIU Z H. A novel "turn-on" mitochondria-targeting near-infrared fluorescent probe for determination and bioimaging cellular hydrogen sulfide[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2019,212:71-77. doi: 10.1016/j.saa.2018.12.046
13. [13]
  MAO Y Y, LI Y B, WANG H J, SUN Y X, YU S L, NIU H Y, YE T Q, GUO L H, LI L, WANG J B. Near-infrared fluorescent probe based on the regulatory dye pK_a for imaging of H₂S in rice roots and living cells[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2024,321124762. doi: 10.1016/j.saa.2024.124762
14. [14]
  FANG W L, HE S, GUO X F, WANG H. A novel near infrared probe with large Stokes shift for detection of H₂S in living cells[J]. Sens. Actuator B-Chem., 2023,375132961. doi: 10.1016/j.snb.2022.132961
15. [15]
  SONG J T, YUAN Y H, ZHU Y J, WANG Y Z, TIAN M Z, FENG F. Research progress of near-infrared fluorescent probes for hydrogen sulfide[J]. Spectrosc. Spectr. Anal., 2022,42(11):3321-3329.
16. [16]
  ZHONG K L, CHEN L, PAN Y X, YAN X M, HOU S H, TANG Y W, GAO X, LI J R, TANG L J. A colorimetric and near-infrared fluorescent probe for detection of hydrogen sulfide and its real multiple applications[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2019,221117135. doi: 10.1016/j.saa.2019.117135
17. [17]
  LI X H, YAN J L, WU W N, ZHAO X L, WANG Y, FAN Y C, XU Z H. A dual-response fluorescent probe for SO₂ and viscosity and imaging application in lysosomes and zebrafish[J]. Microchem. J., 2022,181107653. doi: 10.1016/j.microc.2022.107653
18. [18]
  LINGHU Y N, LIU M, WANG M, LUO Y, LAN W S, WANG J Y. A near-infrared hepatocyte-targeting probe based on tricyanofuran to detect cysteine in vivo: Design, synthesis and evaluation[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2024,322124802. doi: 10.1016/j.saa.2024.124802
19. [19]
  YAN K C, GARDINER J E, SEDGWICK A C, THET N, HEYLEN R A, JAMES T D, JENKINS A T A, HE X P. A TCF-based fluorescent probe to determine nitroreductase (NTR) activity for a broad spectrum of bacterial species[J]. Chem. Commun., 2023,59(53):8278-8281. doi: 10.1039/D3CC00462G
20. [20]
  LI D P, HAN X J, YAN Z Q, CUI Y, MIAO J Y, ZHAO B X. A farred ratiometric fluorescent probe for SO₂ derivatives based on the ESIPT enhanced FRET platform with improved performance[J]. Dyes Pigments., 2018,151:95-101. doi: 10.1016/j.dyepig.2017.12.056
21. [21]
  WANG R, YU F B, CHEN L X, CHEN H, WANG L J, ZHANG W W. A highly selective turn-on near-infrared fluorescent probe for hydrogen sulfide detection and imaging in living cells[J]. Chem. Commun., 2012,48(96):11757-11759. doi: 10.1039/c2cc36088h
22. [22]
  WANG X Y, MIN J, WANG W J, WANG Y, YIN G, WANG R Y. A novel porphyrin-based near-infrared fluorescent probe for hypochlorite detection and its application in vitro and in vivo[J]. Analyst, 2018,143(11):2641-2647. doi: 10.1039/C8AN00586A
23. [23]
  FOSNACHT K G, PLUTH M D. Activity-based fluorescent probes for hydrogen sulfide and related reactive sulfur species[J]. Chem. Rev., 2024,124(7):4124-4257. doi: 10.1021/acs.chemrev.3c00683
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沈阳化工大学材料科学与工程学院沈阳 110142