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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

Frontiers of Chemical Science and Engineering  2022, Vol. 16 Issue (1): 4-33   https://doi.org/10.1007/s11705-021-2041-2
  本期目录
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.

Key wordsbioactive molecules    fluorescent probes    in living cells and in vivo    review
收稿日期: 2020-11-17      出版日期: 2021-12-27
Corresponding Author(s): Wei Zhang,Ping Li   
 引用本文:   
. [J]. Frontiers of Chemical Science and Engineering, 2022, 16(1): 4-33.
Yongqing Zhou, Xin Wang, Wei Zhang, Bo Tang, Ping Li. Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules in live cells and in vivo. Front. Chem. Sci. Eng., 2022, 16(1): 4-33.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-021-2041-2
https://academic.hep.com.cn/fcse/CN/Y2022/V16/I1/4
Fig.1  
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  
Fig.2  
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  
Fig.3  
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  
Fig.4  
Fig.5  
Fig.6  
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  
Fig.7  
Fig.8  
Fig.9  
Fig.10  
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  
Fig.11  
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  
Fig.12  
Fig.13  
Fig.14  
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