N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes for in vivo cell H2S imaging

Yan Shi, Fangjun Huo, Yongkang Yue, Caixia Yin

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Front. Chem. Sci. Eng. ›› 2022, Vol. 16 ›› Issue (1) : 64-71. DOI: 10.1007/s11705-021-2048-8
RESEARCH ARTICLE

N-Positive ion activated rapid addition and mitochondrial targeting ratiometric fluorescent probes for in vivo cell H2S imaging

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Abstract

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.

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Keywords

heterocyclic compound / hydrogen sulfide / ratiometric / mitochondrial targeted

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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 https://doi.org/10.1007/s11705-021-2048-8

References

[1]
McBride H M, Neuspiel M, Wasiak S. Mitochondria: more than just a powerhouse. Current Biology, 2006, 16(14): R551–R560
[2]
Chen Y, Zhu C, Cen J, Bai Y, He W, Guo Z. Ratiometric detection of pH fluctuation in mitochondria with a new fluorescein/cyanine hybrid sensor. Chemical Science (Cambridge), 2015, 6(5): 3187–3194
CrossRef Google scholar
[3]
Lesnefsky E J, Moghaddas S, Tandler B, Kerner J, Hoppel C L. Mitochondrial dysfunction in cardiac disease: ischemia-reperfusion, aging, and heart failure. Journal of Molecular and Cellular Cardiology, 2001, 33(6): 1065–1089
CrossRef Google scholar
[4]
Dorn G W II, Vega R B, Kelly D P. Mitochondrial biogenesis and dynamics in the developing and diseased heart. Genes & Development, 2015, 29(19): 1981–1991
CrossRef Google scholar
[5]
Li J, Yin C, Huo F. Chromogenic and fluorogenic chemosensors for hydrogen sulfide: review of detection mechanisms since the year 2009. RSC Advances, 2015, 5(3): 2191–2206
CrossRef Google scholar
[6]
Zhang Y, Chen Y, Fang H, Shi X, Yuan H, Bai Y, He W, Guo Z. 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
CrossRef Google scholar
[7]
Wu Z, Liang D, Tang X. 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
CrossRef Google scholar
[8]
Zhang X, Tan H, Yan Y, Hang Y, Yu F, Qu X, Hua J. 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
CrossRef Google scholar
[9]
Chen W, Liu C, Peng B, Zhao Y, Pacheco A, Xian M. New fluorescent probes for sulfane sulfurs and the application in bioimaging. Chemical Science (Cambridge), 2013, 4(7): 2892–2896
CrossRef Google scholar
[10]
Yang G, Wu L, Jiang B H, Yang W, Qi J, Cao K, Meng Q, Mustafa A K, Mu W, Zhang S, Snyder S H, Wang R. H2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine γ-lyase. Science, 2008, 322(5901): 587–590
CrossRef Google scholar
[11]
Li H, Yao Q, Fan J, Jiang N, Wang J, Xia J, Peng X. A fluorescent probe for H2S in vivo with fast response and high sensitivity. Chemical Communications, 2015, 51(90): 16225–16228
CrossRef Google scholar
[12]
Gupta N, Reja S I, Bhalla V, Gupta M, Kaur G, Kumar M. 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
CrossRef Google scholar
[13]
Yin C, Huo F, Xu M, Barnes C L, Glass T E A. 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
CrossRef Google scholar
[14]
Hammers M D, Taormina M J, Cerda M M, Montoya L A, Seidenkranz D T, Parthasarathy R, Pluth M D. 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
CrossRef Google scholar
[15]
Gao J, He Y, Chen Y, Song D, Zhang Y, Qi F, Guo Z, He W. Reversible FRET fluorescent probe for ratiometric tracking of endogenous Fe3+ in ferroptosis. Inorganic Chemistry, 2020, 59(15): 10920–10927
CrossRef Google scholar
[16]
Zhou L, Xie L, Liu C, Xiao Y. New trends of molecular probes based on the fluorophore 4-amino-1,8-naphthalimide. Chinese Chemical Letters, 2019, 30(10): 1799–1808
CrossRef Google scholar
[17]
Chen Y, Zhang W, Cai Y, Kwok R, Hu Y, Lam J, Gu X, He Z, Zhao Z, Zheng X, Chen B, Gui C, Tang B Z. 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
CrossRef Google scholar
[18]
Yan Y, Zhang X, Zhang X, Li N, Man H, Chen L, Xiao Y. Ratiometric sensing lysosomal pH in inflammatory macrophages by a BODIPY-rhodamine dyad with restrained FRET. Chinese Chemical Letters, 2020, 31(5): 1091–1094
CrossRef Google scholar
[19]
Chen Y, Bai Y, Han Z, He W, Guo Z. Photoluminescence imaging of Zn2+ in living systems. Chemical Society Reviews, 2015, 14(14): 4517–4546
CrossRef Google scholar
[20]
Lippert A R, Newand R J, Chang C J. Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells. Journal of the American Chemical Society, 2011, 133(26): 10078–10080
CrossRef Google scholar
[21]
Chen S, Chen Z, Ren W, Ai H. Reaction-based genetically encoded fluorescent hydrogen sulfide sensors. Journal of the American Chemical Society, 2012, 134(23): 9589–9592
CrossRef Google scholar
[22]
Bae S K, Heo C H, Choi D J, Sen D, Joe E H, Cho B R, Kim H M. 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
CrossRef Google scholar
[23]
Peng H, Cheng Y, Dai C, King A L, Predmore B L, Lefer D J, Wang B. A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood. Angewandte Chemie International Edition, 2011, 50(41): 9672–9675
[24]
Montoya L A, Pluth M D. Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells. Chemical Communications, 2012, 48(39): 4767–4769
CrossRef Google scholar
[25]
Wu Z, Li Z, Yang L, Han J, Han S. Fluorogenic detection of hydrogen sulfide via reductive unmasking of o-azidomethylbenzoyl-coumarin conjugate. Chemical Communications, 2012, 48(81): 10120–10122
CrossRef Google scholar
[26]
Xuan W, Pan R, Cao Y, Liu K, Wang W. A fluorescent probe capable of detecting H2S at submicromolar concentrations in cells. Chemical Communications, 2012, 48(86): 10669–10671
CrossRef Google scholar
[27]
Sun W, Fan J, Hu C, Cao J, Zhang H, Xiong X, Wang J, Cui S, Sun S, Peng X. A two-photonfluorescent probe with near-infrared emission for hydrogen sulfide imaging in biosystems. Chemical Communications, 2013, 49(37): 3890–3892
CrossRef Google scholar
[28]
Zhang L, Zhu H, Zhao C, Gu X. A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production. Chinese Chemical Letters, 2017, 28(2): 218–221
CrossRef Google scholar
[29]
Chen W, Pacheco A, Takano Y, Day J J, Hanaoka K, Xian M. 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]
Zhao B, Yang Y, Wu Y, Yang B, Chai J, Hu X, Liu B. 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
CrossRef Google scholar
[31]
Zhou T, Yang Y, Zhou K, Jin M, Han M, Li W, Yin C. 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
CrossRef Google scholar
[32]
Yu F, Li P, Song P, Wang B, Zhao J, Han K. An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells. Chemical Communications, 2012, 48(23): 2852–2854
CrossRef Google scholar
[33]
Wan Q, Song Y, Li Z, Gao X, Ma H. In vivo monitoring of hydrogen sulfide using a cresyl violet-based ratiometric fluorescence probe. Chemical Communications, 2013, 49(5): 502–504
CrossRef Google scholar
[34]
Yu C, Li X, Zeng F, Zheng F, Wu S. Carbon-dot-based ratiometric fluorescent sensor for detecting hydrogen sulfide in aqueous media and inside live cells. Chemical Communications, 2013, 49(4): 403–405
CrossRef Google scholar
[35]
Zheng H, Niu L, Chen Y, Wu L, Tung C, Yang Q. Cascade reaction-based fluorescent probe for detection of H2S with the assistance of CTAB micelles. Chinese Chemical Letters, 2016, 27(12): 1793–1796
CrossRef Google scholar
[36]
Zhang C, Sun Q, Zhao L, Gong S, Liu Z. 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
CrossRef Google scholar
[37]
Chen Y, Zhu C, Yang Z, Chen J, He Y, Jiao Y, He W, Qiu L, Cen J, Guo Z. A ratiometric fluorescent probe for rapid detection of hydrogen sulfide in mitochondria. Angewandte Chemie International Edition, 2013, 52(6): 1688–1691
[38]
Zhang W, Huo F, Yin C. Photocontrolled single-/dual-site alternative fluorescence probes distinguishing detection of H2S/SO2 in vivo. Organic Letters, 2019, 21(13): 5277–5280
CrossRef Google scholar
[39]
Zhao C, Zhang X, Li K, Zhu S, Guo Z, Zhang L, Wang F, Fei Q, Luo S, Shi P, Tian H, Zhu W H. 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
CrossRef Google scholar
[40]
Xu G, Yan Q, Lv X, Zhu Y, Xin K, Shi B, Wang R, Chen J, Gao W, Shi P, Imaging of colorectal cancers using activatable nanoprobes with second near-infrared window emission. Angewandte Chemie International Edition, 2018, 57(14): 3626–3630
[41]
Wu Q, Yin C, Wen Y, Zhang Y, Huo F. 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
CrossRef Google scholar
[42]
Fang H, Chen Y, Shi X, Bai Y, Chen Z, Han Z, Zhang Y, He W, Guo Z. Tuning lipophilicity for optimizing the H2S sensing performance of coumarin-merocyanine derivatives. New Journal of Chemistry, 2019, 43(37): 14800–14805
CrossRef Google scholar
[43]
Ma T, Huo F, Chao J, Li J, Yin C. 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
CrossRef Google scholar
[44]
Shu W, Zang S, Wang C, Gao M, Jing J, Zhang X. 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
CrossRef Google scholar
[45]
Zhang Y, Chen Y, Bai Y, Xue X, He W, Guo Z. FRET-based fluorescent ratiometric probes for the rapid detection of endogenous hydrogen sulphide in living cells. Analyst (London), 2020, 145(12): 4233–4238
CrossRef Google scholar
[46]
Wen Y, Huo F, Wang J, Yin C. 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
CrossRef Google scholar
[47]
Wang X, Sun J, Zhang W, Ma X, Lv J, Tang B. 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
CrossRef Google scholar
[48]
Wang J, Wen Y, Huo F, Yin C. 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
CrossRef Google scholar

Acknowledgments

We thank the National Natural Science Foundation of China (Grant Nos. 21775096 and 21878180), One hundred people plan of Shanxi Province, Shanxi Province “1331 project” key innovation team construction plan cultivation team (No. 2018-CT-1), 2018 Xiangyuan County Solid Waste Comprehensive Utilization Science and Technology Project (No. 2018XYSDJS-05), Key R&D Program of Shanxi Province (No. 201903D421069), the Shanxi Province Science Foundation (No. 201901D111015), Shanxi Collaborative Innovation Center of High Value-added Utilization of Coal-related Wastes (No. 2015-10-B3), the Shanxi Province Foundation for Selected Returnee (No. 2019), Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (No. 2019L0031), Project of Graduate Innovation of Shanxi Province (No. 2020), Key R&D and transformation plan of Qinghai Province (No. 2020-GX-101) and Scientific Instrument Center of Shanxi University (No. 201512).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at http://dx.doi.org/10.1007/s11705-021-2048-8 and is accessible for authorized users.

Compliance with Ethics Guidelines

Yan Shi, Fangjun Huo, Yongkang Yue and Caixia Yin declare that they have no conflict of interest. All institutional and national guidelines for the care and use of laboratory animals were followed.

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