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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

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Front. Chem. Sci. Eng.    2022, Vol. 16 Issue (1) : 4-33    https://doi.org/10.1007/s11705-021-2041-2
REVIEW ARTICLE
Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules in live cells and in vivo
Yongqing Zhou, Xin Wang, Wei Zhang(), Bo Tang, Ping Li()
College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Molecular and Nano Probes (Ministry of Education), Institutes of Biomedical Sciences, Shandong Normal University, Jinan 250014, China
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Abstract

The interrelationships and synergistic regulations of bioactive molecules play pivotal roles in physiological and pathological processes involved in the initiation and development of some diseases, such as cancer and neurodegenerative and cardiovascular diseases. Therefore, the simultaneous, accurate and timely detection of two bioactive molecules is crucial to explore their roles and pathological mechanisms in related diseases. Fluorescence imaging associated with small molecular probes has been widely used in the imaging of bioactive molecules in living cells and in vivo due to its excellent performances, including high sensitivity and selectivity, noninvasive properties, real-time and high spatial temporal resolution. Single organic molecule fluorescent probes have been successively developed to simultaneously monitor two biomolecules to uncover their synergistic relationships in living systems. Hence, in this review, we focus on summarizing the design strategies, classifications, and bioimaging applications of dual-response fluorescent probes over the past decade. Furthermore, future research directions in this field are proposed.
Keywords bioactive molecules      fluorescent probes      in living cells and in vivo      review     
Corresponding Author(s): Wei Zhang,Ping Li   
Just Accepted Date: 11 March 2021   Online First Date: 28 April 2021    Issue Date: 27 December 2021
 Cite this article:   
Yongqing Zhou,Xin Wang,Wei Zhang, et al. Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules in live cells and in vivo[J]. Front. Chem. Sci. Eng., 2022, 16(1): 4-33.
 URL:  
https://academic.hep.com.cn/fcse/EN/10.1007/s11705-021-2041-2
https://academic.hep.com.cn/fcse/EN/Y2022/V16/I1/4
Fig.1  Scheme 1 Design strategies of dual-response fluorescent probes for simultaneously monitoring two reactive molecules.
Classification Chemical structure Bioactive molecule Wavelength/nm Detection limit/(mol·L–1) Application Ref.
Two metal ions Al3+ and Cu2+ Al3+: 390/440
Cu2+: 480/520		 Al3+: 7.32 × 10–8
Cu2+: 1.47 × 10–8		 In HeLa cells [22]
Al3+ and Zn2+ Al3+: 500/550
Zn2+: 370/457		 Al3+: 1.2 × 10–5
Zn2+: 3.6 × 10–5		 In mice [23]
Al3+ and Zn2+ Al3+: 330/376
Zn2+: 435/550		 Al3+: 3.79 × 10–6
Zn2+: 1.363 × 10–7		 In C6 cells [24]
Al3+ and Zn2+ Al3+: 384/446
Zn2+: 406/500		 Al3+: 5.37 × 10–8
Zn2+: 7.9 × 10–8		 In HeLa cells and mice [26]
Al3+ and Zn2+ Al3+: 390/504
Zn2+: 390/575		 Al3+: 8.3 × 10–8
Zn2+: 1.24 × 10–7		 In HeLa cells [27]
Hg2+ and Zn2+ Hg2+: 364/580
Zn2+: 364/468		 Hg2+: 2.16 × 10–6
Zn2+: 2.21 × 10–6		 In human prostate cancer cell [28]
Hg2+ and Mg2+ Hg2+: 500/589
Mg2+: 360/523		 Hg2+: 8.0 × 10–8
Mg2+: 1.0 × 10–5		 In HeLa cells [30]
Tab.1  The classifications, chemical structures and applications of fluorescent probes for simultaneously detecting two metal ions
Fig.2  The chemical structures and corresponding sensing mechanisms of H2L and HL-t-Bu in the presence of two metal ions.
Classification Chemical structure Bioactive molecule Wavelength/nm Detection limit/(mol·L–1) Application Ref.
Two ROS ·OH and HClO ·OH: 410/496
HClO: 490/520		 – In RAW264.7 cells and zebrafish [37]
H2O2 and HClO H2O2: 450/550
ClO–: 400/452		 H2O2: 6.46 × 10–8
ClO–: 2.82 × 10–8		 In cells and liver tissue [38]
H2O2 and HClO H2O2: 376/409, 376/640
HClO: 440/520, 440/640		 H2O2: 1.5 × 10–8
HClO: 1.3 × 10–8		 In MCF-7 cells [39]
1O2 and HClO 1O2: 420/475
ClO–: 480/526		 1O2: 3.5 × 10–7
ClO–: 5.3 × 10–8		 In HepG2 cells and in mice [41]
Tab.2  The classifications, chemical structures and applications of fluorescent probes for simultaneously detecting two ROS
Fig.3  (a) Chemical structure and recognition mechanism of FHZ; (b) and (c) confocal microscopy fluorescence imaging of FHZ in RAW264.7 cells under different time and stimulation conditions. Reprinted with permission from Ref. [37], copyright 2016 American Chemical Society.
Classification Chemical structure Bioactive molecule Wavelength/nm Detection limit/(mol·L–1) Application Ref.
Two RSS
Cys and GSH Cys: 450/545
GSH: 580/620		 – In living cells and in mice [47]
Cys and GSH Cys: 480/529
GSH: 480/550		 – In HeLa cell [48]
Cys and GSH Cys: 360/420
GSH: 450/512		 GSH: 5.0 × 10–8 In COS-7 cells [49]
Cys and GSH Cys: 365/420
GSH: 495/537, 495/643		 Cys: 1.7 × 10–7
GSH: 4.6 × 10–7		 In HepG2 cells [50]
H2S and GSH H2S: 515/564
GSH: 430/517		 H2S: 4.2 × 10–8
GSH: 8.7 × 10–8		 In MCF-7 cells [51]
H2S and GSH H2S: 510/587
GSH: 430/501		 H2S: 2.855 × 10–5
GSH: 7.55 × 10–6		 In RAW cells [52]
H2S and H2Sn H2S: 360/452
H2Sn: 515/542		 H2S: 1.5 × 10–7
H2Sn: 2.4 × 10–8		 In HeLa cells [4]
H2S and H2Sn H2S: 410/519, 410/606
H2Sn: 410/468, 410/606		 H2S: 3.4 × 10–8
H2Sn: 2.1 × 10–8		 In RAW264.7 cells [53]
HSO3– and biothiols Cys: 497/590
HSO3–: 350/445, 350/590		 Cys: 8.18 × 10–6
HSO3–: 7.22 × 10–6		 In HeLa cells [54]
SO2 and biothiols SO2: 390/495
Biothiols: 556/665		 SO2: 6.0 × 10–8
Biothiols: 2.02 × 10–7		 In HeLa cells [55]
Cys and Hcy Cys: 400/480
Hcy: 452/542		 Cys: 1.99 × 10–6
Hcy: 6.1 × 10–7		 In living cells [56]
GSH and H2Sn GSH: 430/540
H2Sn: 366/465		 GSH: 5.6 × 10–8
H2Sn: 4.0 × 10–8		 In RAW264.7 cells [57]
Cys and SO2 Cys: 460/550, 460/664
HSO3–: 470/560		 Cys: 3.0 × 10–8
HSO3–:1.1 × 10–8		 In MCF-7 cells [58]
Cys and bisulfite Cys: 570/640
HSO3–: 450/540, 450/640		 Cys: 2.0 × 10–8
HSO3–: 3.0 × 10–9		 In MCF-7 cells, zebrafish and mice [59]
HS– and HSO3– HS–: 500/581
HSO3–: 460/515		 HS–: 1.2 × 10–7
HSO3–: 2.0 × 10–8		 In HepG2 cells and LO-2 cells [60]
Tab.3  The classifications, chemical structures and applications of fluorescent probes for simultaneously detecting two RSS
Fig.4  The chemical structures and recognition mechanisms of OP and POP.
Fig.5  The chemical structure of FRET-based DDP-1 that facilitates the detection of H2Sn and H2S.
Fig.6  (A) The proposed sensing mechanism of ACC-SePh for monitoring H2Sn and GSH; (B) fluorescence imaging of GSH and H2Sn in living RAW264.7 cells; (C) fluorescence imaging of endogenously produced H2Sn in living RAW264.7 cells. Reprinted with permission from Ref. [57], copyright 2017 American Chemical Society.
Classification Chemical structure Bioactive molecule Wavelength/nm Detection limit/(mol·L–1) Application Ref.
One ROS and one RSS HClO and SO2 ClO–: 395/425, 544/585
HSO3–: 395/482		 ClO–: 1.66 × 10–8
HSO3–: 2.5 × 10–7		 In MCF-7, EC1, HeLa cells [63]
HClO and SO2 ClO–: 410/500, 410/625
SO2: 330/410, 440/625		 ClO–: 1.25 × 10–8
SO2: 3.5 × 10–9		 In HeLa cells and zebrafish [64]
HClO and SO2 ClO–: 425/525, 425/600
HSO3–: 350/425, 460/600		 ClO–: 1.52 × 10–8
HSO3–: 8.0 × 10–9		 In HeLa cells and zebrafish [65]
One RSS and one ROS H2S and H2O2 H2S: 325/413, 475/627
H2O2: 325/486		 H2S: 5.8 × 10–8
H2O2: 4.4 × 10–8		 In HeLa cells and zebrafish [66]
H2S and H2O2 H2S: 450/550
H2O2: 400/460		 H2S: 5.23 × 10–4
H2O2: 1.21 × 10–4		 In HeLa cells [67]
H2S and H2O2 H2S: 488/520
H2O2: 400/460		 – In HEK293 cells [68]
One ROS and one RSS HClO and H2S ClO–: 545/580
H2S: 360/445		 ClO–: 1.98 × 10–8
H2S: 1.92 × 10–7		 In RAW264.7 cells and mice [69]
HClO and H2S ClO–: 550/580
H2S: 380/448		 ClO–: 7.3 × 10–8
H2S: 3.5 × 10–7		 In HeLa cells [70]
HClO and H2S ClO–: 440/520, 440/640
H2S: 400/450		 ClO–: 1.7 × 10–8
H2S: 2.6 × 10–8		 In MCF-7 cells [71]
Tab.4  The classifications, chemical structures and applications of fluorescent probes for simultaneously detecting one ROS and one RSS
Fig.7  Chemical structure and sensing mechanism proposed of NPCIA for the simultaneous detection of HClO and SO2.
Fig.8  The chemical structure of the TCAB and sensing mechanism proposed for detecting H2O2 and H2S.
Fig.9  The chemical structure and sensing mechanism proposed for RPC-1 for the discrimination of H2S and HClO.
Fig.10  (A) TPM images of RPC-1 endogenous H2S and HClO in RAW264.7 cells after drug treatment; (B) TPM images of the RPC-1 of rat liver slices. Reprinted with permission from Ref. [69], copyright 2018 American Chemical Society.
Classification Chemical structure Bioactive molecule Wavelength/nm Detection limit/(mol·L–1) Application Ref.
One RSS
and One RNS		 NO and H2S NO: 550/570
H2S: 425/539		 – In L929 cells [76]
NO and GSH NO: 505/528
GSH: 538/558		 NO: 3.1 × 10–8
GSH: 5.6 × 10–8		 In macrophages [77]
Tab.5  The classifications, chemical structures and applications of fluorescent probes for simultaneously detecting one RSS and one RNS
Fig.11  The chemical structure of Naph-RhB and the sensing mechanism proposed for monitoring NO and H2S.
Classification Chemical structure Bioactive molecule Wavelength/nm Detection limit Application Ref.
One ROS/one RNS H2O2 and NO H2O2: 400/460
NO: 550/580		 – In HeLa and RAW264.7 cells [80]
One ROS/one macromolecule H2O2 and ATP H2O2: 710/470
ATP: 710/590		 In living cells and zebrafish [81]
One RSS/one macromolecule H2S and ALP H2S: 360/445
ALP: 510/545		 In HeLa cells [82]
Two macromolecules ATP and NRT ATP: 540/580
NRT: 420/520		 ATP: 0.05 mmol·L–1
NRT: 0.12 mg·mL–1		 In HeLa cells [83]
GCD and PDE GCD: 340/460
PDE: 340/656		 GCD: 1 U In Huh7 cells [84]
One RSS/F- F– and H2S F–: 365/553
HS–: 550/633		 F–: 1.45 × 10–8
HS–: 5.73 × 10–8		 In HeLa cells [85]
Tab.6  The classifications, chemical structures and applications of fluorescent probes for simultaneously detecting two other biomolecules
Fig.12  Chemical structure and proposed detection mechanism of FP-H2O2-NO for discrimination of H2O2 and ATP.
Fig.13  (A) Fluorescence imaging of FP-H2O2-NO in living RAW264.7 cells in the absence or presence of stimuli; (B) Fluorescence imaging of FP-H2O2-NO in living RAW264.7 cells in the absence or presence of stimuli and scavengers. Reprinted with permission from Ref. [80], copyright 2011 American Chemical Society.
Fig.14  Chemical structure and proposed detection mechanism of TFP for discrimination of H2O2 and ATP.
1 H Sies, D P Jones. Reactive oxygen species (ROS) as pleiotropic physiological signaling agents. Nature Reviews. Molecular Cell Biology, 2020, 21(7): 363–383
https://doi.org/10.1038/s41580-020-0230-3
2 H Sies, C Berndt, D P Jones. Oxidative stress. Annual Review of Biochemistry, 2017, 86(1): 715–748
https://doi.org/10.1146/annurev-biochem-061516-045037
3 L L Wu, C Huang, B P Emery, A C Sedgwick, S D Bull, X P He, H Tian, J Y Yoon, J L Sessler, T D James. Forster resonance energy transfer (FRET)-based small-molecule sensors and imaging agents. Chemical Society Reviews, 2020, 49(15): 5110–5139
https://doi.org/10.1039/C9CS00318E
4 W Chen, A Pacheco, Y K Takano, J J Day, K Hanaoka, M Xian. A single fluorescent probe to visualize hydrogen sulfide and hydrogen polysulfides with different fluorescence signals. Angewandte Chemie International Edition, 2016, 55(34): 9993–9996
https://doi.org/10.1002/anie.201604892
5 X Q Chen, F Wang, J Y Hyun, T W Wei, J Qiang, X T Ren, I J Shin, J Y Yoon. Recent progress in the development of fluorescent, luminescent and colorimetric probes for detection of reactive oxygen and nitrogen species. Chemical Society Reviews, 2016, 45(10): 2976–3016
https://doi.org/10.1039/C6CS00192K
6 Z Xu, L Xu. Fluorescent probes for the selective detection of chemical species inside mitochondria. Chemical Communications, 2016, 52(6): 1094–1119
https://doi.org/10.1039/C5CC09248E
7 Z Q Mao, M T Ye, W Hu, X X Ye, Y Y Wang, H J Zhang, C Y Li, Z H Liu. Design of a ratiometric two-photon probe for imaging of hypochlorous acid (HClO) in wounded tissues. Chemical Science (Cambridge), 2018, 9(28): 6035–6040
https://doi.org/10.1039/C8SC01697F
8 X H Li, X H Gao, W Shi, H M Ma. Design strategies for water-soluble small molecular chromogenic and fluorogenic probes. Chemical Reviews, 2014, 114(1): 590–659
https://doi.org/10.1021/cr300508p
9 I S Harris, G D DeNicola. The complex interplay between antioxidants and ROS in cancer. Trends in Cell Biology, 2020, 30(6): 440–451
https://doi.org/10.1016/j.tcb.2020.03.002
10 X Y Jiao, Y Li, J Y Niu, X L Xie, X Wang, B Tang. Small-molecule fluorescent probes for imaging and detection of reactive oxygen, nitrogen, and sulfur species in biological systems. Analytical Chemistry, 2018, 90(1): 533–555
https://doi.org/10.1021/acs.analchem.7b04234
11 D Wu, A C Sedgwick, T Gunnlaugsson, E U Akkaya, J Y Yoon, T D Jame. Fluorescent chemosensors: the past, presen and future. Chemical Society Reviews, 2017, 46(23): 7105–7123
https://doi.org/10.1039/C7CS00240H
12 P Gao, W Pan, N Li, B Tang. Fluorescent probes for organelle-targeted bioactive species imaging. Chemical Science (Cambridge), 2019, 10(24): 6035–6071
https://doi.org/10.1039/C9SC01652J
13 T Ueno, T Nagano. Fluorescence probes for sensing and imaging. Nature Methods, 2011, 8(8): 642–645
https://doi.org/10.1038/nmeth.1663
14 J L Zhu, Z Xu, Y Y Yang, L Xu. Small-molecule fluorescent probes for specific detection and imaging of chemical species inside lysosomes. Chemical Communications, 2019, 55(47): 6629–6671
https://doi.org/10.1039/C9CC03299A
15 L Yuan, W Y Lin, K B Zhang, S S Zhu. FRET-based small-molecule fluorescent probes: rational design and bioimaging applications. Accounts of Chemical Research, 2013, 46(7): 1462–1473
https://doi.org/10.1021/ar300273v
16 L W He, B L Dong, Y Liu, W Y Lin. Fluorescent chemosensors manipulated by dual/triple interplaying sensing mechanisms. Chemical Society Reviews, 2016, 45(23): 6449–6461
https://doi.org/10.1039/C6CS00413J
17 R R Crichton, J L Pierre. Old iron, young copper: from Mars to Venus. Biometals, 2011, 14(2): 99–112
https://doi.org/10.1023/A:1016710810701
18 X Wang, P Li, W Zhang, B Tang. Recent advances in fluorescence imaging of bioactive molecules in neurons and in vivo. Chinese Journal of Analytical Chemistry, 2019, 47(10): 1537–1548
https://doi.org/10.1016/S1872-2040(19)61191-6
19 M H Lee, J S Kim, J L Sessler. Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules. Chemical Society Reviews, 2015, 44(13): 4185–4191
https://doi.org/10.1039/C4CS00280F
20 L M Miller, Q Wang, T P Telivala, R J Smith, A Lanzirotti, J Miklossy. Synchrotron-based infrared and X-ray imaging shows focalized accumulation of Cu and Zn co-localized with β-amyloid deposits in Alzheimer’s disease. Journal of Structural Biology, 2006, 155(1): 30–37
https://doi.org/10.1016/j.jsb.2005.09.004
21 N Nakao, E V Frodl, H Widner, E Carlson, F A Eggerding, C J Epstein, P Brundin. Overexpressing Cu/Zn superoxide dismutase enhances survival of transplanted neurons in a rat model of Parkinson’s disease. Nature Medicine, 1995, 1(3): 226–231
https://doi.org/10.1038/nm0395-226
22 L J Hou, J Feng, Y B Wang, C A Dong, S M Shuang, Y Wang. Single fluorescein-based probe for selective colorimetric and fluorometric dual sensing of Al3+ and Cu2+. Sensors and Actuators. B, Chemical, 2017, 247: 451–460
https://doi.org/10.1016/j.snb.2017.03.027
23 A Roy, U Shee, A Mukherjee, S K Mandal, P Roy. Rhodamine-based dual chemosensor for Al3+ and Zn2+ ions with distinctly separated excitation and emission wavelengths. ACS Omega, 2019, 4(4): 6864–6875
https://doi.org/10.1021/acsomega.9b00475
24 A Hazra, A Roy, A Mukherjee, G P Maiti, P Roy. Remarkable difference in Al3+ and Zn2+ sensing properties of quinoline based isomers. Dalton Transactions (Cambridge, England), 2018, 47(39): 13972–13989
https://doi.org/10.1039/C8DT02856G
25 W Sun, M Li, J L Fan, X J Peng. Activity-based sensing and theranostic probes based on photoinduced electron transfer. Accounts of Chemical Research, 2019, 52(10): 2818–2831
https://doi.org/10.1021/acs.accounts.9b00340
26 G Zhao, G Wei, Z Q Yan, B Y Guo, S Y Guang, R L Wu, H Y Xu. A multiple fluorescein-based turn-on fluorophore (FHCS) identified for simultaneous determination and living imaging of toxic Al3+ and Zn2+ by improved stokes shift. Analytica Chimica Acta, 2020, 1095: 185–196
https://doi.org/10.1016/j.aca.2019.10.025
27 H Y Liu, T Q Liu, J Li, Y M Zhang, J H Li, J Song, J L Qu, W Y Wong. A simple Schiff base as dual-responsive fluorescent sensor for bioimaging recognition of Zn2+ and Al3+ in living cells. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2018, 6(34): 5435–5442
https://doi.org/10.1039/C8TB01743C
28 S Erdemir, M Yuksekogu, S Karakurt, O Kocyigit. Dual-channel fluorescent probe based on bisphenol A-rhodamine for Zn2+ and Hg2+ through different signaling and its bioimaging studies. Sensors and Actuators B Chemiscal, 2017, 241: 230–238
29 L L Wu, A C Sedgwick, X L Sun, S D Bull, X P He, T D James. Reaction-based fluorescent probes for the detection and imaging of reactive oxygen, nitrogen, and sulfur species. Accounts of Chemical Research, 2019, 52(9): 2582–2597
https://doi.org/10.1021/acs.accounts.9b00302
30 Y Zhao, B Z Zheng, J Du, D Xiao, L Yang. A fluorescent “turn-on” probe for the dual-channel detection of Hg(II) and Mg(II) and its application of imaging in living cells. Talanta, 2011, 85(4): 2194–2201
https://doi.org/10.1016/j.talanta.2011.07.070
31 D Andina, J C Leroux, P Luciani. Ratiometric fluorescent probes for the detection of reactive oxygen species. Chemistry (Weinheim an der Bergstrasse, Germany), 2017, 23(55): 13547–13573
https://doi.org/10.1002/chem.201702458
32 J D Schoenfeld, Z A Sibenaller, K A Mapuskar, B A Wagner, K L Cramer-Morales, M Furqan, S Sandhu, T L Carlisle, M C Smith, T Abu Hejleh, et al. O2.– and H2O2-mediated disruption of Fe metabolism causes the differential susceptibility of NSCLC and GBM cancer cells to pharmacological ascorbate. Cancer Cell, 2017, 31(4): 487–500
https://doi.org/10.1016/j.ccell.2017.02.018
33 Z R Lou, P Li, K L Han. Redox-responsive fluorescent probes with different design strategies. Accounts of Chemical Research, 2015, 48(5): 1358–1368
https://doi.org/10.1021/acs.accounts.5b00009
34 B Hassannia, P Vandenabeele, T Vanden Berghe. Targeting ferroptosis to iron out cancer. Cancer Cell, 2019, 35(6): 830–849
https://doi.org/10.1016/j.ccell.2019.04.002
35 E T Chouchani, V R Pell, E Gaude, D Aksentijević, S Y Sundier, E L Robb, A Logan, S M Nadtochiy, E N J Ord, A C Smith, et al. Ischaemic accumulation of succinate controls reperfusion injury through mitochondrial ROS. Nature, 2014, 515(7527): 431–435
https://doi.org/10.1038/nature13909
36 F He, L Zuo. Redox roles of reactive oxygen species in cardiovascular disease. International Journal of Molecular Sciences, 2015, 16(11): 27770–27780
https://doi.org/10.3390/ijms161126059
37 R Zhang, J Zhao, G Han, Z Liu, C Liu, C Zhang, B Liu, C Jiang, R Liu, T Zhao, M Y Han, Z Zhang. Real-time discrimination and versatile profiling of spontaneous ROS in living organisms with a single fluorescent probe. Journal of the American Chemical Society, 2016, 138(11): 3769–3778
https://doi.org/10.1021/jacs.5b12848
38 Y C Du, B W Wang, D Jin, M R Li, Y Li, X L Yan, X Q Zhou, L G Chen. Dual-site fluorescent probe for multi-response detection of ClO– and H2O2 and bio-imaging. Analytica Chimica Acta, 2020, 1103: 174–182
https://doi.org/10.1016/j.aca.2019.12.059
39 J L Han, X J Liu, H Q Xiong, J P Wang, B H Wang, X Z Song, W Wang. Investigation of the relationship between H2O2 and HClO in living cells by a bifunctional, dual-ratiometric responsive fluorescent probe. Analytical Chemistry, 2020, 92(7): 5134–5142
https://doi.org/10.1021/acs.analchem.9b05604
40 S H Park, N Kwon, J H Lee, J Y Yoon, I Shin. Synthetic ratiometric fluorescent probes for detection of ions. Chemical Society Reviews, 2020, 49(1): 143–179
https://doi.org/10.1039/C9CS00243J
41 L L Long, Y Y Han, W G Liu, Q Chen, D D Yin, L L Li, F Yuan, Z X Han, A H Gong, K Wang. Simultaneous discrimination of hypochlorite and single oxygen during sepsis by a dual-functional fluorescent probe. Analytical Chemistry, 2020, 92(8): 6072–6080
https://doi.org/10.1021/acs.analchem.0c00492
42 Y K Yue, F J Huo, F Q Cheng, X J Zhu, T Mafireyi, R M Strongin, C X Yin. Functional synthetic probes for selective targeting and multi-analyte detection and imaging. Chemical Society Reviews, 2019, 48(15): 4155–4177
https://doi.org/10.1039/C8CS01006D
43 X Q Chen, Y Zhou, X J Peng, J Y Yoon. Fluorescent and colorimetric probes for detection of thiols. Chemical Society Reviews, 2010, 39(6): 2120–2135
https://doi.org/10.1039/b925092a
44 V S Lin, W Chen, M Xian, C J Chang. Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems. Chemical Society Reviews, 2015, 44(14): 4596–4618
https://doi.org/10.1039/C4CS00298A
45 F B Yu, X Y Han, L X Che. Fluorescent probes for hydrogen sulfide detection and bioimaging. Chemical Communications, 2014, 50(82): 12234–12249
https://doi.org/10.1039/C4CC03312D
46 Y Q Zhou, P Li, N N Fan, X Wang, X N Liu, L J Wu, W Zhang, W Zhang, C L Ma, B Tang. In situ visualization of peroxisomal peroxynitrite in the livers of mice with acute liver injury induced by carbon tetrachloride using a new two-photon fluorescent probe. Chemical Communications, 2019, 55(47): 6767–6770
https://doi.org/10.1039/C9CC02483B
47 H X Zhang, J Liu, B Hu, L F Wang, Z Yang, X Han, J J Wang, W Bai, W Guo. Dual-channel fluorescence diagnosis of cancer cells/tissues assisted by OATP transporters and cysteine/glutathione. Chemical Science (Cambridge), 2018, 9(12): 3209–3214
https://doi.org/10.1039/C7SC05407F
48 F Lv, X Guo, H Wu, H Li, B Tang, C J Yu, E H Hao, L J Jiao. Direct sulfonylation of BODIPY dyes with sodiumsulfinates through oxidative radical hydrogen substitution at the a-position. Chemical Communications, 2020, 56(99): 15577–15580
https://doi.org/10.1039/D0CC07259A
49 J Liu, Y Q Sun, Y Y Huo, H X Zhang, L F Wang, P Zhang, D Song, Y W Shi, W Guo. Simultaneous fluorescence sensing of Cys and GSH from different emission channels. Journal of the American Chemical Society, 2014, 136(2): 574–577
https://doi.org/10.1021/ja409578w
50 X L Fu, X G Chen, H Li, W Feng, Q H Song. Quinolone-based fluorescent probe for distinguishing detection of Cys and GSH through different fluorescence channels. New Journal of Chemistry, 2020, 44(32): 13781–13787
https://doi.org/10.1039/D0NJ03274C
51 H L Li, W Peng, W P Feng, Y X Wang, G F Chen, S X Wang, S H Li, H F Li, K R Wang, J C Zhang. A novel dual-emission fluorescent probe for simultaneous detection of H2S and GSH. Chemical Communications, 2016, 52(25): 4628–4631
https://doi.org/10.1039/C6CC00973E
52 J Li, C X Yin, Y B Zhang, Y K Yue, J B Chao, F J Huo. High selective distinguishable detection GSH and H2S based on steric configuration of molecular in vivo. Dyes and Pigments, 2020, 172: 107826
https://doi.org/10.1016/j.dyepig.2019.107826
53 X X Zhao, F R He, Y P Dai, F L Ma, Z J Qi. A single fluorescent probe for one- and two-photon imaging hydrogen sulfide and hydrogen polysulfides with different fluorescence signals. Dyes and Pigments, 2020, 172: 107818
https://doi.org/10.1016/j.dyepig.2019.107818
54 M Y Li, P C Cui, K Li, J H Feng, M M Zou, X Q Yu. Dual-site fluorescent probe for highly selective and sensitive detection of sulfite and biothiols. Chinese Chemical Letters, 2018, 29(6): 992–994
https://doi.org/10.1016/j.cclet.2017.11.011
55 X Y Wu, Y Wang, Y H Liu, X Q Yu. Dual-site lysosome-targeted fluorescent probe for separate detection of endogenous biothiols and SO2 in living Cells. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2018, 6(25): 4232–4238
https://doi.org/10.1039/C8TB01152D
56 Y Li, W M Liu, H Y Zhang, M Q Wang, J S Wu, J C Ge, P F Wang. Dual emission channels for simultaneous sensing Cys and Hcy in living cells. Chemistry, an Asian Journal, 2017, 12(16): 2098–2103
https://doi.org/10.1002/asia.201700583
57 W Q Chen, X X Yue, H Zhang, W X Li, L L Zhang, Q Xiao, C S Huang, J R Sheng, X Z Song. Simultaneous detection of glutathione and hydrogen polysulfides from different emission channels. Analytical Chemistry, 2017, 89(23): 12984–12991
https://doi.org/10.1021/acs.analchem.7b04033
58 X P Yang, W Y Liu, J Tang, P Li, H B Weng, Y Ye, M Xian, B Tang, Y F Zhao. A multi-signal mitochondria-targeted fluorescent probe for real-time visualization of cysteine metabolism in living cells and animals. Chemical Communications, 2018, 54(81): 11387–11390
https://doi.org/10.1039/C8CC05418E
59 F F Zhao, Z Y Zha, J Tang, B B Zhang, X P Yang, X Z Song, Y Ye. A bond energy transfer based difunctional fluorescent sensor for Cys and bisulfite. Talanta, 2020, 214: 120884
https://doi.org/10.1016/j.talanta.2020.120884
60 C X Yin, T Yu, Y B Gan, L Zhou, M L Liu, Y Y Zhang, H T Li, P Yin, S Z Yao. A novel fluorescent probe with dual-sites for simultaneously monitoring metabolisms of cysteine in living cells and zebrafishes. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2020, 241: 118602
https://doi.org/10.1016/j.saa.2020.118602
61 J L Yin, Y Y Ma, G H Li, M Peng, W Y Lin. A versatile small-molecule fluorescence scaffold: carbazole derivatives for bioimaging. Coordination Chemistry Reviews, 2020, 412: 213257
https://doi.org/10.1016/j.ccr.2020.213257
62 H Zhu, J L Fan, J J Du, X J Peng. Fluorescent probes for sensing and imaging within specific cellular organelles. Accounts of Chemical Research, 2016, 49(10): 2115–2126
https://doi.org/10.1021/acs.accounts.6b00292
63 H W Niu, J Tang, X F Zhua, Z P Li, Y R Zhang, Y Ye, Y F Zhao. Three-channel fluorescent probe to image mitochondrial stress. Chemical Communications, 2020, 56(56): 7710–7713
https://doi.org/10.1039/D0CC02668A
64 K Dou, Q Fu, G Chen, F B Yu, Y X Liu, Z P Cao, G L Li, X N Zhao, L Xia, L X Chen, H Wang, J You. A novel dual-ratiometric-response fluorescent probe for SO2/ClO– detection in cells and in vivo and its application in exploring the dichotomous role of SO2 under the ClO– induced oxidative stress. Biomaterials, 2017, 133: 82–93
https://doi.org/10.1016/j.biomaterials.2017.04.024
65 K Dou, C Guang, F B Yu, Z W Sun, G L Li, X N Zhao, L X Chen, J M You. A two-photon ratiometric fluorescent probe for the synergistic detection of mitochondrial SO2/HClO crosstalk in cells and in vivo. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2017, 5(42): 8389–8398
https://doi.org/10.1039/C7TB01900A
66 L Yang, Y Zhang, X J Ren, B H Wang, Z G Yang, X Z Song, W Wang. Fluorescent detection of dynamic H2O2/H2S redox event in living cells and organisms. Analytical Chemistry, 2020, 92(6): 4387–4394
https://doi.org/10.1021/acs.analchem.9b05270
67 N Velusamy, N Thirumalaivasan, K N Bobba, A Podder, S P Wu, S Bhuniya. FRET-based dual channel fluorescent probe for detecting endogenous/exogenous H2O2/H2S formation through multicolor images. Journal of Photochemistry and Photobiology. B, Biology, 2019, 191: 99–106
https://doi.org/10.1016/j.jphotobiol.2018.12.016
68 L Yi, L Wei, R Y Wang, C Y Zhang, J Zhang, T W Tan, X Zhen. A dual-response fluorescent probe reveals the H2O2-induced H2S biogenesis through a cystathionine β-synthase pathway. Chemistry (Weinheim an der Bergstrasse, Germany), 2015, 21(43): 15167–15172
https://doi.org/10.1002/chem.201502832
69 X Y Jiao, Y S Xiao, Y Li, M W Liang, X L Xie, X Wang, B Tang. Evaluating drug-induced liver injury and its remission via discrimination and imaging of HClO and H2S with a two-photon fluorescent probe. Analytical Chemistry, 2018, 90(12): 7510–7516
https://doi.org/10.1021/acs.analchem.8b01106
70 M G Ren, Z H Li, B B Deng, L Wang, W Y Lin. Single fluorescent probe separately and continuously visualize H2S and HClO in lysosomes with different fluorescence signals. Analytical Chemistry, 2019, 91(4): 2932–2938
https://doi.org/10.1021/acs.analchem.8b05116
71 X X Yue, J P Wang, J L Han, B H Wang, X Z Song. A dual-ratiometric fluorescent probe for individual and continuous detection of H2S and HClO in living cells. Chemical Communications, 2020, 56(19): 2849–2852
https://doi.org/10.1039/C9CC10028H
72 Y Li, X L Xie, X E Yang, M M Li, X Y Jiao, Y H Sun, X Wang, B Tang. Two-photon fluorescent probe for revealing drug-induced hepatotoxicity via mapping fluctuation of peroxynitrite. Chemical Science (Cambridge), 2017, 8(5): 4006–4011
https://doi.org/10.1039/C7SC00303J
73 N N Wang, X Y Yu, K Zhang, C A Mirkin, J S Li. Upconversion nanoprobes for the ratiometric luminescent sensing of nitric oxide. Journal of the American Chemical Society, 2017, 139(36): 12354–12357
https://doi.org/10.1021/jacs.7b06059
74 M Fransen, M Nordgren, B Wang, O Apanasets. Role of peroxisomes in ROS/RNS-metabolism: implications for human disease. Biochimica et Biophysica Acta, 2012, 1822(3): 1363–1373
https://doi.org/10.1016/j.bbadis.2011.12.001
75 N T Moldogazieva, I M Mokhosoev, N B Feldman, S V Lutsenko. ROS and RNS signaling: adaptive redox switches though oxidative/nitrosative protein modifications. Free Radical Research, 2018, 52(5): 507–543
https://doi.org/10.1080/10715762.2018.1457217
76 P S Zhang, J Li, B W Li, J S Xu, F Zeng, J Lv, S Z Wu. A logic gate-based fluorescent sensor for detecting H2S and NO in aqueous media and inside live cells. Chemical Communications, 2015, 51(21): 4414–4416
https://doi.org/10.1039/C4CC09737H
77 X X Chen, L Y Niu, N Shao, Q Z Yang. BODIPY-based fluorescent probe for dual-channel detection of nitric oxide and glutathione: visualization of cross-talk in living cells. Analytical Chemistry, 2019, 91(7): 4301–4306
https://doi.org/10.1021/acs.analchem.9b00169
78 J J Zhang, X Z Chai, X P He, H J Kim, J Y Yoon, H Tian. Fluorogenic probes for disease-relevant enzymes. Chemical Society Reviews, 2019, 48(2): 683–722
https://doi.org/10.1039/C7CS00907K
79 H M Kim, B R Cho. Small-molecule two-photon probes for bioimaging applications. Chemical Reviews, 2015, 115(11): 5014–5055
https://doi.org/10.1021/cr5004425
80 L Yuan, W Y Lin, Y N Xie, B Chen, S S Zhu. Single fluorescent probe responds to H2O2, NO, and H2O2/NO with three different sets of fluorescence signals. Journal of the American Chemical Society, 2012, 134(2): 1305–1315
https://doi.org/10.1021/ja2100577
81 Z Wu, M M Liu, Z C Liu, Y Tian. Real-time imaging and simultaneous quantification of mitochondrial H2O2 and ATP in neurons with a single two-photon fluorescence lifetime-based probe. Journal of the American Chemical Society, 2020, 142(16): 7532–7541
https://doi.org/10.1021/jacs.0c00771
82 P Ou, R Zhang, Z Liu, X Tian, G Han, B Liu, Z Hu, Z Zhang. Gasotransmitter Regulation of Phosphatase Activity in Live Cells Studied by Three-Channel Imaging Correlation. Angewandte Chemie International Edition, 2019, 131(8): 2283–2287
https://doi.org/10.1002/ange.201811391
83 Y Fang, W Shi, Y M Hu, X H Li, H M Ma. A dual-function fluorescent probe for monitoring the degrees of hypoxia in living cells via the imaging of nitroreductase and adenosine triphosphate. Chemical Communications, 2018, 54(43): 5454–5457
https://doi.org/10.1039/C8CC02209G
84 Y H Li, H Wang, J H Li, J Zheng, X H Xu, R H Yang. Simultaneous intracellular β-D-glucosidase and phosphodiesterase I activities measurements based on a triple-signaling fluorescent probe. Analytical Chemistry, 2011, 83(4): 1268–1274
https://doi.org/10.1021/ac102095j
85 L Fu, F F Tian, L Lai, Y Liu, P D Harvey, F L Jiang. A ratiometric “two-in-one” fluorescent chemodosimeter for fluoride and hydrogen sulfide. Sensors and Actuators. B, Chemical, 2014, 193: 701–707
https://doi.org/10.1016/j.snb.2013.12.038
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