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

Front. Chem. Sci. Eng. ›› 2022, Vol. 16 ›› Issue (1) : 64 -71.

PDF (3247KB)
Front. Chem. Sci. Eng. ›› 2022, Vol. 16 ›› Issue (1) : 64 -71. DOI: 10.1007/s11705-021-2048-8
RESEARCH ARTICLE
RESEARCH ARTICLE

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

Author information +
History +
PDF (3247KB)

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.

Graphical abstract

Keywords

heterocyclic compound / hydrogen sulfide / ratiometric / mitochondrial targeted

Cite this article

Download citation ▾
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 DOI:10.1007/s11705-021-2048-8

登录浏览全文

4963

注册一个新账户 忘记密码

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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

[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

RIGHTS & PERMISSIONS

Higher Education Press

AI Summary AI Mindmap
PDF (3247KB)

Supplementary files

FCE-20105-OF-SY_suppl_1

6096

Accesses

0

Citation

Detail

Sections
Recommended

AI思维导图

/