Citation: Zheng Hai-Rong, Niu Li-Ya, Chen Yu-Zhe, Wu Li-Zhu, Tung Chen-Ho, Yang Qing-Zheng. Cascade reaction-based fluorescent probe for detection of H₂S with the assistance of CTAB micelles[J]. Chinese Chemical Letters, ;2016, 27(12): 1793-1796. doi: 10.1016/j.cclet.2016.04.023 shu

Cascade reaction-based fluorescent probe for detection of H₂S with the assistance of CTAB micelles

a.
Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
College of Chemistry, Beijing Normal University, Beijing 100875, China
c.
University of the Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Niu Li-Ya, niuly@mail.ipc.ac.cn
Received Date: 29 March 2016
Revised Date: 25 April 2016
Accepted Date: 28 April 2016
Available Online: 18 December 2016

Figures(6)

We report a turn-on fluorescent probe for H₂S through a cascade reaction using a new trap group 4-(bromomethyl)benzoate, based on excited-state intramolecular proton transfer (ESIPT) sensing mechanism. The probe showed good selectivity and high sensitivity towards H₂S and it was capable of detecting and imaging H₂S in living HeLa cells, indicating its potential biological applications.
- Hydrogen sulfide,
- Fluorescent probe,
- Cascade reaction,
- ESIPT,
- Micelles
1. [1]
  C. Szabó. Hydrogen sulphide and its therapeutic potential[J]. Nat. Rev. Drug. Discov., 2007,6:917-935. doi: 10.1038/nrd2425
2. [2]
  M. Ishigami, K. Hiraki, K. Umemura. A source of hydrogen sulfide and a mechanism of its release in the brain,[J]. Antioxid. Redox Signal., 2009,11:205-214. doi: 10.1089/ars.2008.2132
3. [3]
  G.A. Benavides, G.L. Squadrito, R.W. Mills. Hydrogen sulfide mediates the vasoactivity of garlic[J]. Proc. Natl. Acad. Sci. U.S.A., 2007,104:17977-17982. doi: 10.1073/pnas.0705710104
4. [4]
  S. Singh, D. Padovani, R.A. Leslie, T. Chiku, R. Banerjee. Relative contributions of cystathionine b-synthase and g-cystathionase to H₂S biogenesis via alternative trans-sulfuration reactions[J]. J. Biol. Chem., 2009,284:22457-22466. doi: 10.1074/jbc.M109.010868
5. [5]
  S. Singh, R. Banerjee. PLP-dependent H₂S biogenesis[J]. Biochim. Biophys. Acta, 2011,1814:1518-1527. doi: 10.1016/j.bbapap.2011.02.004
6. [6]
  K. Eto, T. Asada, K. Arima, T. Makifuchi, H. Kimura. Brain hydrogen sulfide is severely decreased in Alzheimer's disease[J]. Biochem. Biophys. Res. Commun., 2002,293:1485-1488. doi: 10.1016/S0006-291X(02)00422-9
7. [7]
  P. Kamoun, M.-C. Belardinelli, A. Chabli, K. Lallouchi, B. Chadefaux-Vekemans. Endogenous hydrogen sulfide overproduction in Down syndrome[J]. Am. J. Med. Genet. A, 2003,116:310-311.
8. [8]
  W. Yang, G.D. Yang, X.M. Jia, L.Y. Wu, R. Wang. Activation of KATP channels by H₂S in rat insulin-secreting cells and the underlying mechanisms[J]. J. Physiol. (Lond.), 2005,569:519-531. doi: 10.1113/jphysiol.2005.097642
9. [9]
  S. Fiorucci, E. Antonelli, A. Mencarelli. The third gas:H₂S regulates perfusion pressure in both the isolated and perfused normal rat liver and in cirrhosis[J]. Hepatology, 2005,42:539-548. doi: 10.1002/(ISSN)1527-3350
10. [10]
  L.M. Siegel. A direct microdetermination for sulfide[J]. Anal. Biochem., 1965,11:126-122. doi: 10.1016/0003-2697(65)90051-5
11. [11]
  E. Fischer. Formation of methylene blue in response to hydrogen sulfide[J]. Ber. Dtsch. Chem. Ges., 1983,16:2234-2236.
12. [12]
  U. Hannestad, S. Margheri, B. Sö rbo. A sensitive gas chromatographic method for determination of protein associated sulfur[J]. Anal. Biochem., 1989,178:394-398. doi: 10.1016/0003-2697(89)90659-3
13. [13]
  J. Furne, A. Saeed, M.D. Levitt. Whole tissue hydrogen sulfide concentrations are orders of magnitude lower than presently accepted values[J]. Am. J. Physiol. Regul. Integr. Comp. Physiol., 2008,295:1479-1485. doi: 10.1152/ajpregu.90566.2008
14. [14]
  L.Y. Niu, Y.Z. Chen, H.R. Zheng. Design strategies of fluorescent probes for selective detection among biothiols[J]. Chem. Soc. Rev., 2015,44:6143-6160. doi: 10.1039/C5CS00152H
15. [15]
  X. Zhou, S. Lee, Z.C. Xu, J. Yoon. Recent progress on the development of chemosensors for gases[J]. Chem. Rev., 2015,115:7944-8000. doi: 10.1021/cr500567r
16. [16]
  L.Y. Niu, Y.S. Guan, Y.Z. Chen. BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine[J]. J. Am. Chem. Soc., 2012,134:18928-18931. doi: 10.1021/ja309079f
17. [17]
  V.S. Lin, C.J. Chang. Fluorescent probes for sensing and imaging biological hydrogen sulfide[J]. Curr. Opin. Chem. Biol., 2012,16:595-601. doi: 10.1016/j.cbpa.2012.07.014
18. [18]
  C.C. Zhao, X.L. Zhang, K.B. Li. Fö rster resonance energy transfer switchable self-assembled micellar nanoprobe:ratiometric fluorescent trapping of endogenous H₂S generation via fluvastatin-stimulated upregulation[J]. J. Am. Chem. Soc., 2015,137:8490-8498. doi: 10.1021/jacs.5b03248
19. [19]
  X. Wang, J. Sun, W.H. Zhang. A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells[J]. Chem. Sci., 2013,4:2551-2556. doi: 10.1039/c3sc50369k
20. [20]
  Z.S. Wu, Y.L. Feng, B. Geng, J.Y. Liu, X.J. Tang. Fluorogenic sensing of H₂S in blood and living cells via reduction of aromatic dialkylamino N-oxide[J]. RSC Adv., 2014,4:30398-30401. doi: 10.1039/C4RA03677H
21. [21]
  H.J. Peng, Y.F. Cheng, C.F. Dai. A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood[J]. Angew. Chem. Int. Ed., 2011,50:9672-9675. doi: 10.1002/anie.201104236
22. [22]
  S. Chen, Z.J. Chen, W. Ren, H.W. Ai. Reaction-based genetically encoded fluorescent hydrogen sulfide sensors[J]. J. Am. Chem. Soc., 2012,134:9589-9592. doi: 10.1021/ja303261d
23. [23]
  K.J. Wu, G.Q. Li, Y. Li, L.X. Dai, S.L. You. Reaction-based genetically encoded fluorescent hydrogen sulfide sensors[J]. Chem. Commun., 2011,47:493-495. doi: 10.1039/C0CC01769H
24. [24]
  C.R. Liu, J. Pan, S. Li. Capture and visualization of hydrogen sulfide by a fluorescent probe[J]. Angew. Chem. Int. Ed., 2011,50:10327-10329. doi: 10.1002/anie.201104305
25. [25]
  C.R. Liu, B. Peng, S. Li. Reaction based fluorescent probes for hydrogen sulfide[J]. Org. Lett., 2012,14:2184-2187. doi: 10.1021/ol3008183
26. [26]
  K. Sasakura, K. Hanaoka, N. Shibuya. Development of a highly selective fluorescence probe for hydrogen sulfide[J]. J. Am. Chem. Soc., 2011,133:18003-18005. doi: 10.1021/ja207851s
27. [27]
  F.P. Hou, L. Huang, P.X. Xi. A retrievable and highly selective fluorescent probe for monitoring sulfide and imaging in living cells[J]. Inorg. Chem., 2012,51:2454-2460. doi: 10.1021/ic2024082
28. [28]
  X.W. Cao, W.Y. Lin, K.B. Zheng, L.W. He. A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether[J]. Chem. Commun., 2012,48:10529-10531. doi: 10.1039/c2cc34031c
29. [29]
  T.Y. Liu, Z.C. Xu, D.R. Spring, J.N. Cui. A lysosome-targetable fluorescent probe for imaging hydrogen sulfide in living cells[J]. Org. Lett., 2013,15:2310-2313. doi: 10.1021/ol400973v
30. [30]
  S.D. Liu, L.W. Zhang, P.P. Zhou. HBT-based chemosensors for the detection of fluoride through deprotonation process:experimental and DFT studies[J]. RSC Adv., 2015,5:19983-19988. doi: 10.1039/C4RA13532F
31. [31]
  L.H. Geng, X.F. Yang, Y.G. Zhong, Z. Li, H. Li. "Quinone-phenol" transduction activated excited-state intramolecular proton transfer:a new strategy toward ratiometric fluorescent probe for sulfite in living cells[J]. Dyes Pigm., 2015,120:213-219. doi: 10.1016/j.dyepig.2015.04.016
32. [32]
  S. Sahana, G. Mishra, S. Sivakumar, P.K. Bharadwaj. A 2-(2[Prime or minute]-hydroxyphenyl)benzothiazole (HBT)-quinoline conjugate:a highly specific fluorescent probe for Hg²⁺ based on ESIPT and its application in bioimaging[J]. Dalton Trans., 2015,44:20139-20146. doi: 10.1039/C5DT03719K
33. [33]
  S. Goswami, A. Manna, S. Paul. FRET based ‘red-switch’ for Al³⁺ over ESIPT based ‘green-switch’ for Zn²⁺:dual channel detection with live-cell imaging on a dyad platform[J]. RSC Adv., 2014,4:34572-34576. doi: 10.1039/C4RA05714G
34. [34]
  X.F. Yang, Q. Huang, Y.G. Zhong. A dual emission fluorescent probe enables simultaneous detection of glutathione and cysteine/homocysteine[J]. Chem. Sci., 2014,5:2177-2183. doi: 10.1039/c4sc00308j
35. [35]
  Q.S. Liu, C.L. Zhang, X.Q. Wang. Benzothiazole-pyimidine-based BF₂ complex for selective detection of cysteine[J]. Chem. Asian J., 2016,11:202-206. doi: 10.1002/asia.v11.2
36. [36]
  C.C. Zhao, X.A. Li, F.Y. Wang. Target-triggered NIR emission with a large stokes shift for the detection and imaging of cysteine in living cells[J]. Chem. Asian J., 2014,9:1777-1781. doi: 10.1002/asia.v9.7
37. [37]
  S. Goswami, S. Das, K. Aich. A chemodosimeter for the ratiometric detection of hydrazine based on return of ESIPT and its application in live-cell imaging[J]. Org. Lett., 2013,15:5412-5415. doi: 10.1021/ol4026759
38. [38]
  D.P. Murale, H. Kim, W.S. Choi, D.G. Churchill. Highly selective excited state intramolecular proton transfer (ESIPT)-based superoxide probing[J]. Org. Lett., 2013,15:3946-3949. doi: 10.1021/ol4017222
39. [39]
  S.M. Aly, A. Usman, M. AlZayer. Solvent-dependent excited-state hydrogen transfer and intersystem crossing in 2-(20-Hydroxyphenyl)-Benzothiazole[J]. J. Phys. Chem. B, 2015,119:2596-2603. doi: 10.1021/jp508777h
40. [40]
  A.R. Lippert, E.J. New, C.J. Chang. Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells[J]. J. Am. Chem. Soc., 2011,133:10078-10080. doi: 10.1021/ja203661j
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Cascade reaction-based fluorescent probe for detection of H2S with the assistance of CTAB micelles

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Cascade reaction-based fluorescent probe for detection of H₂S with the assistance of CTAB micelles