N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes for in vivo cell H2S imaging
Yan Shi1,2, Fangjun Huo3, Yongkang Yue1, Caixia Yin1()
1. Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China 2. College of Food Sciences, Shanxi Normal University, Linfen 041004, China 3. Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China
Heterocyclic compound quinoline and its derivatives exist in natural compounds and have a broad spectrum of biological activity. They play an important role in the design of new structural entities for medical applications. Similarly, indoles and their derivatives are found widely in nature. Amino acids, alkaloids and auxin are all derivatives of indoles, as are dyes, and their condensation with aldehydes makes it easy to construct reaction sites for nucleophilic addition agents. In this work, we combine these two groups organically to construct a rapid response site (within 30 s) for H2S, and at the same time, a ratiometric fluorescence response is presented throughout the process of H2S detection. As such, the lower detection limit can reach 55.7 nmol/L for H2S. In addition, cell imaging shows that this probe can be used for the mitochondrial targeted detection of endogenous and exogenous H2S. Finally, this probe application was verified by imaging H2S in nude mice.
. [J]. Frontiers of Chemical Science and Engineering, 2022, 16(1): 64-71.
Yan Shi, Fangjun Huo, Yongkang Yue, Caixia Yin. N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes for in vivo cell H2S imaging. Front. Chem. Sci. Eng., 2022, 16(1): 64-71.
H M McBride, M Neuspiel, S. Wasiak Mitochondria: more than just a powerhouse. Current Biology, 2006, 16(14): R551–R560
2
Y Chen, C Zhu, J Cen, Y Bai, W He, Z Guo. Ratiometric detection of pH fluctuation in mitochondria with a new fluorescein/cyanine hybrid sensor. Chemical Science (Cambridge), 2015, 6(5): 3187–3194 https://doi.org/10.1039/C4SC04021J
3
E J Lesnefsky, S Moghaddas, B Tandler, J Kerner, C L Hoppel. Mitochondrial dysfunction in cardiac disease: ischemia-reperfusion, aging, and heart failure. Journal of Molecular and Cellular Cardiology, 2001, 33(6): 1065–1089 https://doi.org/10.1006/jmcc.2001.1378
4
G W II Dorn, R B Vega, D P Kelly. Mitochondrial biogenesis and dynamics in the developing and diseased heart. Genes & Development, 2015, 29(19): 1981–1991 https://doi.org/10.1101/gad.269894.115
5
J Li, C Yin, F Huo. Chromogenic and fluorogenic chemosensors for hydrogen sulfide: review of detection mechanisms since the year 2009. RSC Advances, 2015, 5(3): 2191–2206 https://doi.org/10.1039/C4RA11870G
6
Y Zhang, Y Chen, H Fang, X Shi, H Yuan, Y Bai, W He, Z Guo. A ratiometric fluorescent probe for imaging enzyme dependent hydrogen sulfide variation in the mitochondria and in living mice. Analyst (London), 2020, 145(15): 5123–5127 https://doi.org/10.1039/D0AN00910E
7
Z Wu, D Liang, X Tang. Visualizing Hydrogen sulfide in mitochondria and lysosome of living cells and in tumors of living mice with positively charged fluorescent chemosensors. Analytical Chemistry, 2016, 88(18): 9213–9218 https://doi.org/10.1021/acs.analchem.6b02459
8
X Zhang, H Tan, Y Yan, Y Hang, F Yu, X Qu, J Hua. Targetable N-annulated perylene-based colorimetric and ratiometric near-infrared fluorescent probes for the selective detection of hydrogen sulfide in mitochondria, lysosomes, and serum. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2017, 5(11): 2172–2180 https://doi.org/10.1039/C7TB00210F
9
W Chen, C Liu, B Peng, Y Zhao, A Pacheco, M Xian. New fluorescent probes for sulfane sulfurs and the application in bioimaging. Chemical Science (Cambridge), 2013, 4(7): 2892–2896 https://doi.org/10.1039/c3sc50754h
10
G Yang, L Wu, B H Jiang, W Yang, J Qi, K Cao, Q Meng, A K Mustafa, W Mu, S Zhang, S H Snyder, R Wang. H2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine γ-lyase. Science, 2008, 322(5901): 587–590 https://doi.org/10.1126/science.1162667
11
H Li, Q Yao, J Fan, N Jiang, J Wang, J Xia, X Peng. A fluorescent probe for H2S in vivo with fast response and high sensitivity. Chemical Communications, 2015, 51(90): 16225–16228 https://doi.org/10.1039/C5CC06612C
12
N Gupta, S I Reja, V Bhalla, M Gupta, G Kaur, M Kumar. A bodipy based dual functional probe for the detection of hydrogen sulfide and H2S induced apoptosis in cellular systems. Chemical Communications, 2015, 51(54): 10875–10878 https://doi.org/10.1039/C5CC02984H
13
C Yin, F Huo, M Xu, C L Barnes, T E A Glass. NIR, special recognition on HS−/CN− colorimetric and fluorescent imaging material for endogenous H2S based on nucleophilic addition. Sensors and Actuators. B, Chemical, 2017, 252: 592–599 https://doi.org/10.1016/j.snb.2017.06.044
14
M D Hammers, M J Taormina, M M Cerda, L A Montoya, D T Seidenkranz, R Parthasarathy, M D Pluth. A bright fluorescent probe for H2S enables analyte-responsive, 3D imaging in live zebrafish using light sheet fluorescence microscopy. Journal of the American Chemical Society, 2015, 137(32): 10216–10223 https://doi.org/10.1021/jacs.5b04196
15
J Gao, Y He, Y Chen, D Song, Y Zhang, F Qi, Z Guo, W He. Reversible FRET fluorescent probe for ratiometric tracking of endogenous Fe3+ in ferroptosis. Inorganic Chemistry, 2020, 59(15): 10920–10927 https://doi.org/10.1021/acs.inorgchem.0c01412
16
L Zhou, L Xie, C Liu, Y Xiao. New trends of molecular probes based on the fluorophore 4-amino-1,8-naphthalimide. Chinese Chemical Letters, 2019, 30(10): 1799–1808 https://doi.org/10.1016/j.cclet.2019.07.051
17
Y Chen, W Zhang, Y Cai, R Kwok, Y Hu, J Lam, X Gu, Z He, Z Zhao, X Zheng, B Chen, C Gui, B Z Tang. AIEgens for dark through-bond energy transfer: design, synthesis, theoretical study and application in ratiometric Hg2+ sensing. Chemical Science (Cambridge), 2017, 8(3): 2047–2055 https://doi.org/10.1039/C6SC04206F
18
Y Yan, X Zhang, X Zhang, N Li, H Man, L Chen, Y Xiao. Ratiometric sensing lysosomal pH in inflammatory macrophages by a BODIPY-rhodamine dyad with restrained FRET. Chinese Chemical Letters, 2020, 31(5): 1091–1094 https://doi.org/10.1016/j.cclet.2019.10.025
19
Y Chen, Y Bai, Z Han, W He, Z Guo. Photoluminescence imaging of Zn2+ in living systems. Chemical Society Reviews, 2015, 14(14): 4517–4546 https://doi.org/10.1039/C5CS00005J
20
A R Lippert, R J Newand, C J Chang. Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells. Journal of the American Chemical Society, 2011, 133(26): 10078–10080 https://doi.org/10.1021/ja203661j
21
S Chen, Z Chen, W Ren, H Ai. Reaction-based genetically encoded fluorescent hydrogen sulfide sensors. Journal of the American Chemical Society, 2012, 134(23): 9589–9592 https://doi.org/10.1021/ja303261d
22
S K Bae, C H Heo, D J Choi, D Sen, E H Joe, B R Cho, H M Kim. A ratiometric two-photon fluorescent probe reveals reduction in mitochondrial H2S production in parkinson’s disease gene knockout astrocytes. Journal of the American Chemical Society, 2013, 135(26): 9915–9923 https://doi.org/10.1021/ja404004v
23
H Peng, Y Cheng, C Dai, A L King, B L Predmore, D J Lefer, B Wang. A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood. Angewandte Chemie International Edition, 2011, 50(41): 9672–9675
24
L A Montoya, M D Pluth. Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells. Chemical Communications, 2012, 48(39): 4767–4769 https://doi.org/10.1039/c2cc30730h
25
Z Wu, Z Li, L Yang, J Han, S Han. Fluorogenic detection of hydrogen sulfide via reductive unmasking of o-azidomethylbenzoyl-coumarin conjugate. Chemical Communications, 2012, 48(81): 10120–10122 https://doi.org/10.1039/c2cc34682f
26
W Xuan, R Pan, Y Cao, K Liu, W Wang. A fluorescent probe capable of detecting H2S at submicromolar concentrations in cells. Chemical Communications, 2012, 48(86): 10669–10671 https://doi.org/10.1039/c2cc35602c
27
W Sun, J Fan, C Hu, J Cao, H Zhang, X Xiong, J Wang, S Cui, S Sun, X Peng. A two-photonfluorescent probe with near-infrared emission for hydrogen sulfide imaging in biosystems. Chemical Communications, 2013, 49(37): 3890–3892 https://doi.org/10.1039/c3cc41244j
28
L Zhang, H Zhu, C Zhao, X Gu. A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production. Chinese Chemical Letters, 2017, 28(2): 218–221 https://doi.org/10.1016/j.cclet.2016.07.008
29
W Chen, A Pacheco, Y 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
30
B Zhao, Y Yang, Y Wu, B Yang, J Chai, X Hu, B Liu. To re-evaluate the emission mechanism, AIE activity of 5-azidofluorescein and its reaction with H2S and NO. Sensors and Actuators. B, Chemical, 2018, 256: 79–88 https://doi.org/10.1016/j.snb.2017.10.020
31
T Zhou, Y Yang, K Zhou, M Jin, M Han, W Li, C Yin. Efficiently mitochondrial targeting fluorescent imaging of H2S in vivo based on a conjugate-lengthened cyanine NIR fluorescent probe. Sensors and Actuators. B, Chemical, 2019, 301: 127116 https://doi.org/10.1016/j.snb.2019.127116
32
F Yu, P Li, P Song, B Wang, J Zhao, K Han. An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells. Chemical Communications, 2012, 48(23): 2852–2854 https://doi.org/10.1039/c2cc17658k
33
Q Wan, Y Song, Z Li, X Gao, H Ma. In vivo monitoring of hydrogen sulfide using a cresyl violet-based ratiometric fluorescence probe. Chemical Communications, 2013, 49(5): 502–504 https://doi.org/10.1039/C2CC37725J
34
C Yu, X Li, F Zeng, F Zheng, S Wu. Carbon-dot-based ratiometric fluorescent sensor for detecting hydrogen sulfide in aqueous media and inside live cells. Chemical Communications, 2013, 49(4): 403–405 https://doi.org/10.1039/C2CC37329G
35
H Zheng, L Niu, Y Chen, L Wu, C Tung, Q Yang. Cascade reaction-based fluorescent probe for detection of H2S with the assistance of CTAB micelles. Chinese Chemical Letters, 2016, 27(12): 1793–1796 https://doi.org/10.1016/j.cclet.2016.04.023
36
C Zhang, Q Sun, L Zhao, S Gong, Z Liu. A BODIPY-based ratiometric probe for sensing and imaging hydrogen polysulfides in living cells. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2019, 223: 117295 https://doi.org/10.1016/j.saa.2019.117295
37
Y Chen, C Zhu, Z Yang, J Chen, Y He, Y Jiao, W He, L Qiu, J Cen, Z Guo. A ratiometric fluorescent probe for rapid detection of hydrogen sulfide in mitochondria. Angewandte Chemie International Edition, 2013, 52(6): 1688–1691
38
W Zhang, F Huo, C Yin. Photocontrolled single-/dual-site alternative fluorescence probes distinguishing detection of H2S/SO2 in vivo. Organic Letters, 2019, 21(13): 5277–5280 https://doi.org/10.1021/acs.orglett.9b01879
39
C Zhao, X Zhang, K Li, S Zhu, Z Guo, L Zhang, F Wang, Q Fei, S Luo, P Shi, H Tian, W H Zhu. Förster resonance energy transfer switchable self-assembled micellar nanoprobe: ratiometric fluorescent trapping of endogenous H2S generation via fluvastatin-stimulated upregulation. Journal of the American Chemical Society, 2015, 137(26): 8490–8498 https://doi.org/10.1021/jacs.5b03248
40
G Xu, Q Yan, X Lv, Y Zhu, K Xin, B Shi, R Wang, J Chen, W Gao, P Shi, et al. Imaging of colorectal cancers using activatable nanoprobes with second near-infrared window emission. Angewandte Chemie International Edition, 2018, 57(14): 3626–3630
41
Q Wu, C Yin, Y Wen, Y Zhang, F Huo. An ICT lighten ratiometric and NIR fluorogenic probe to visualize endogenous/exogenous hydrogen sulphide and imaging in mice. Sensors and Actuators. B, Chemical, 2019, 288: 507–511 https://doi.org/10.1016/j.snb.2019.03.053
42
H Fang, Y Chen, X Shi, Y Bai, Z Chen, Z Han, Y Zhang, W He, Z Guo. Tuning lipophilicity for optimizing the H2S sensing performance of coumarin-merocyanine derivatives. New Journal of Chemistry, 2019, 43(37): 14800–14805 https://doi.org/10.1039/C9NJ03846A
43
T Ma, F Huo, J Chao, J Li, C Yin. A highly sensitive ratiometric fluorescent probe for real-time monitoring sulfur dioxide as the viscosity change in living cells and mice. Sensors and Actuators. B, Chemical, 2020, 320: 128044 https://doi.org/10.1016/j.snb.2020.128044
44
W Shu, S Zang, C Wang, M Gao, J Jing, X Zhang. An endoplasmic reticulum-targeted ratiometric fluorescent probe for the sensing of hydrogen sulfide in living cells and zebrafish. Analytical Chemistry, 2020, 92(14): 9982–9988 https://doi.org/10.1021/acs.analchem.0c01623
45
Y Zhang, Y Chen, Y Bai, X Xue, W He, Z Guo. FRET-based fluorescent ratiometric probes for the rapid detection of endogenous hydrogen sulphide in living cells. Analyst (London), 2020, 145(12): 4233–4238 https://doi.org/10.1039/D0AN00531B
46
Y Wen, F Huo, J Wang, C Yin. Molecular isomerization triggered by H2S to an NIR accessible first direct visualization of Ca2+-dependent production in living HeLa cells. Journal of Materials Chemistry. B, Materials for Biology and Medicine, 2019, 7(43): 6855–6860 https://doi.org/10.1039/C9TB01885A
47
X Wang, J Sun, W Zhang, X Ma, J Lv, B Tang. A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells. Chemical Science (Cambridge), 2013, 4(6): 2551–2556 https://doi.org/10.1039/c3sc50369k
48
J Wang, Y Wen, F Huo, C Yin. A highly sensitive fluorescent probe for hydrogen sulfide based on dicyanoisophorone and its imaging in living cells. Sensors and Actuators. B, Chemical, 2019, 294: 141–147 https://doi.org/10.1016/j.snb.2019.05.038
