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
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.
. [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.
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
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
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
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
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