Fluorescein-derived fl uorescent probe for cellular hydrogen sulfi de imaging

注册 English

Fluorescein-derived fl uorescent probe for cellular hydrogen sulfi de imaging

Hui-Ying Liu , Miao Zhao , Qing-Long Qiao , Hai-Jing Lang , Jing-Zhe Xu , Zhao-Chao Xu

Citation: Hui-Ying Liu, Miao Zhao, Qing-Long Qiao, Hai-Jing Lang, Jing-Zhe Xu, Zhao-Chao Xu. Fluorescein-derived fl uorescent probe for cellular hydrogen sulfi de imaging[J]. Chinese Chemical Letters, 2014, 25(7): 1060-1064. doi: 10.1016/j.cclet.2014.05.010 shu

shu

Fluorescein-derived fl uorescent probe for cellular hydrogen sulfi de imaging

通讯作者: Jing-Zhe Xu,
Zhao-Chao Xu,

基金项目:
We thank financial supports from the National Natural Science Foundation of China (No. 21276251) (No. 21276251)

State Key Laboratory of Fine Chemicals of China (No. KF1105). (No. KF1105)

摘要: In this work, a fluorescein-derived fluorescent probe for H₂S based on the thiolysis of dinitrophenyl ether is reported. This probe exhibits turn-on fluorescence imaging of H₂S in living cells and bulk solutions with excellent selectivity. The reaction mechanism was explained by means of absorption, fluorescence and HPLC-MS.

关键词:

English

Fluorescein-derived fl uorescent probe for cellular hydrogen sulfi de imaging

1.
a Department of Chemistry, Yanbian University, Yanji 133002, China;
2.
b Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China

Corresponding author: Jing-Zhe Xu, Zhao-Chao Xu,

Received Date: 24 January 2014
Fund Project:

Abstract: In this work, a fluorescein-derived fluorescent probe for H₂S based on the thiolysis of dinitrophenyl ether is reported. This probe exhibits turn-on fluorescence imaging of H₂S in living cells and bulk solutions with excellent selectivity. The reaction mechanism was explained by means of absorption, fluorescence and HPLC-MS.

Key words:

1. [1] H. Kimura, Hydrogen sulfide: its production, release and functions, Amino Acids 41 (2011) 113-121.[1] H. Kimura, Hydrogen sulfide: its production, release and functions, Amino Acids 41 (2011) 113-121.
2. [2] L. Li, P. Rose, P.K. Moore, Hydrogen sulfide and cell signaling, Annu. Rev. Pharmacol. Toxicol. 51 (2011) 169-187.[2] L. Li, P. Rose, P.K. Moore, Hydrogen sulfide and cell signaling, Annu. Rev. Pharmacol. Toxicol. 51 (2011) 169-187.
3. [3] R.A. Dombkowski, M.J. Russell, K.R. Olson, Hydrogen sulfide as an endogenous regulator of vascular smooth muscle tone in trout, Am. J. Physiol. Regul. Integr. Comp. Physiol. 286 (2004) R678-R685.[3] R.A. Dombkowski, M.J. Russell, K.R. Olson, Hydrogen sulfide as an endogenous regulator of vascular smooth muscle tone in trout, Am. J. Physiol. Regul. Integr. Comp. Physiol. 286 (2004) R678-R685.
4. [4] Y. Kaneko, Y. Kimura, H. Kimura, I. Niki, _L-Cysteine inhibits insulin release from the pancreatic β-cell: possible involvement of metabolic production of hydrogen sulfide, a novel gasotransmitter, Diabetes 55 (2006) 1391-1397.[4] Y. Kaneko, Y. Kimura, H. Kimura, I. Niki, _L-Cysteine inhibits insulin release from the pancreatic β-cell: possible involvement of metabolic production of hydrogen sulfide, a novel gasotransmitter, Diabetes 55 (2006) 1391-1397.
5. [5] R.C.O. Zanardo, V. Brancaleone, E. Distrutti, et al., Hydrogen sulfide is an endogenous modulator of leukocyte-mediated inflammation, FASEB J. 20 (2006) 2118-2120.[5] R.C.O. Zanardo, V. Brancaleone, E. Distrutti, et al., Hydrogen sulfide is an endogenous modulator of leukocyte-mediated inflammation, FASEB J. 20 (2006) 2118-2120.
6. [6] K. Eto, T. Asada, K. Arima, T. Makifuchi, H. Kimura, Brain hydrogen sulfide is severely decreased in Alzheimer's disease, Biochem. Biophys. Res. Commun. 293 (2002) 1485-1488.[6] K. Eto, T. Asada, K. Arima, T. Makifuchi, H. Kimura, Brain hydrogen sulfide is severely decreased in Alzheimer's disease, Biochem. Biophys. Res. Commun. 293 (2002) 1485-1488.
7. [7] P. Kamoun, M.C. Belardinelli, A. Chabli, K. Lallouchi, B. Chadefaux-Vekemans, Endogenous hydrogen sulfide overproduction in Down syndrome, Am. J. Med. Genet. A 116A (2003) 310-311.[7] P. Kamoun, M.C. Belardinelli, A. Chabli, K. Lallouchi, B. Chadefaux-Vekemans, Endogenous hydrogen sulfide overproduction in Down syndrome, Am. J. Med. Genet. A 116A (2003) 310-311.
8. [8] W. Yang, G. Yang, X. Jia, L. Wu, R. Wang, Activation of KATP channels by H₂S in rat insulin-secreting cells and the underlying mechanisms, J. Physiol. 569 (2005) 519-531.[8] W. Yang, G. Yang, X. Jia, L. Wu, R. Wang, Activation of KATP channels by H₂S in rat insulin-secreting cells and the underlying mechanisms, J. Physiol. 569 (2005) 519-531.
9. [9] S. Fiorucci, E. Antonelli, A. Mencarelli, et al., The third gas: H₂S regulates perfusion pressure in both the isolated and perfused normal rat liver and in cirrhosis, Hepatology 42 (2005) 539-548.[9] S. Fiorucci, E. Antonelli, A. Mencarelli, et al., The third gas: H₂S regulates perfusion pressure in both the isolated and perfused normal rat liver and in cirrhosis, Hepatology 42 (2005) 539-548.
10. [10] C. Szabo, Hydrogen sulphide and its therapeutic potential, Nat. Rev. Drug Discov. 6 (2007) 917-935.[10] C. Szabo, Hydrogen sulphide and its therapeutic potential, Nat. Rev. Drug Discov. 6 (2007) 917-935.
11. [11] H. Peng, W. Chen, S. Burroughs, B. Wang, Recent advances in fluorescent probes for the detection of hydrogen sulfide, Curr. Org. Chem. 17 (2013) 641-653.[11] H. Peng, W. Chen, S. Burroughs, B. Wang, Recent advances in fluorescent probes for the detection of hydrogen sulfide, Curr. Org. Chem. 17 (2013) 641-653.
12. [12] A.R. Lippert, Designing reaction-based fluorescent probes for selective hydrogen sulfide detection, J. Inorg. Biochem. 133 (2014) 136-142.[12] A.R. Lippert, Designing reaction-based fluorescent probes for selective hydrogen sulfide detection, J. Inorg. Biochem. 133 (2014) 136-142.
13. [13] V.S. Lin, C.J. Chang, Fluorescent probes for sensing and imaging biological hydrogen sulfide, Curr. Opin. Chem. Biol. 16 (2012) 595-601.[13] V.S. Lin, C.J. Chang, Fluorescent probes for sensing and imaging biological hydrogen sulfide, Curr. Opin. Chem. Biol. 16 (2012) 595-601.
14. [14] N. Kumar, V. Bhalla, M. Kumar, Recent developments of fluorescent probes for the detection of gasotransmitters (NO, CO and H2S), Coord. Chem. Rev. 257 (2013) 2335-2347.[14] N. Kumar, V. Bhalla, M. Kumar, Recent developments of fluorescent probes for the detection of gasotransmitters (NO, CO and H2S), Coord. Chem. Rev. 257 (2013) 2335-2347.
15. [15] T. Chen, Y. Zheng, Z. Xu, et al., A red emission fluorescent probe for hydrogen sulfide and its application in living cells imaging, Tetrahedron Lett. 54 (2013) 2980-2982.[15] T. Chen, Y. Zheng, Z. Xu, et al., A red emission fluorescent probe for hydrogen sulfide and its application in living cells imaging, Tetrahedron Lett. 54 (2013) 2980-2982.
16. [16] Y. Zheng, M. Zhao, Q. Qiao, et al., A near-infrared fluorescent probe for hydrogen sulfide in living cells, Dyes Pigments 98 (2013) 367-371.[16] Y. Zheng, M. Zhao, Q. Qiao, et al., A near-infrared fluorescent probe for hydrogen sulfide in living cells, Dyes Pigments 98 (2013) 367-371.
17. [17] Y.H. Li, J.F. Yang, C.H. Liu, J.S. Li, R.H. Yang, Colorimetric and fluorescent detection of biological thiols in aqueous solution, Chin. Chem. Lett. 24 (2013) 96-98.[17] Y.H. Li, J.F. Yang, C.H. Liu, J.S. Li, R.H. Yang, Colorimetric and fluorescent detection of biological thiols in aqueous solution, Chin. Chem. Lett. 24 (2013) 96-98.
18. [18] Q. Liu, L. Xue, D.J. Zhu, G.P. Li, H. Jiang, Highly selective two-photon fluorescent probe for imaging of nitric oxide in living cells, Chin. Chem. Lett. 25 (2014) 19-23.[18] Q. Liu, L. Xue, D.J. Zhu, G.P. Li, H. Jiang, Highly selective two-photon fluorescent probe for imaging of nitric oxide in living cells, Chin. Chem. Lett. 25 (2014) 19-23.
19. [19] S. Wu, Y.J. Wei, Y.B. Wang, et al., Ratiometric and selective two-photon fluorescent probe based on PET-ICT for imaging Zn²⁺ in living cells and tissues, Chin. Chem. Lett. 25 (2014) 93-98.[19] S. Wu, Y.J. Wei, Y.B. Wang, et al., Ratiometric and selective two-photon fluorescent probe based on PET-ICT for imaging Zn²⁺ in living cells and tissues, Chin. Chem. Lett. 25 (2014) 93-98.
20. [20] X.H. Yang, S. Sun, P. Liu, et al., A novel fluorescent detection for PDGF-BB based on dsDNA-templated copper nanoparticles, Chin. Chem. Lett. 25 (2014) 9-14.[20] X.H. Yang, S. Sun, P. Liu, et al., A novel fluorescent detection for PDGF-BB based on dsDNA-templated copper nanoparticles, Chin. Chem. Lett. 25 (2014) 9-14.
21. [21] H. Zheng, X.Q. Zhan, Q.N. Bian, X.J. Zhang, Advances in modifying fluorescein and rhodamine fluorophores as fluorescent chemosensors, Chem. Commun. 49 (2013) 429-447.[21] H. Zheng, X.Q. Zhan, Q.N. Bian, X.J. Zhang, Advances in modifying fluorescein and rhodamine fluorophores as fluorescent chemosensors, Chem. Commun. 49 (2013) 429-447.
22. [22] X. Chen, T. Pradhan, F. Wang, J.S. Kim, J. Yoon, Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives, Chem. Rev. 112 (2011) 1910-1956.[22] X. Chen, T. Pradhan, F. Wang, J.S. Kim, J. Yoon, Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives, Chem. Rev. 112 (2011) 1910-1956.
23. [23] G.M. van Dam, G. Themelis, L.M.A. Crane, et al., Intraoperative tumor-specific fluorescence imaging in ovarian cancer by folate receptor-[alpha] targeting: first in-human results, Nat. Med. 17 (2011) 1315-1319.[23] G.M. van Dam, G. Themelis, L.M.A. Crane, et al., Intraoperative tumor-specific fluorescence imaging in ovarian cancer by folate receptor-[alpha] targeting: first in-human results, Nat. Med. 17 (2011) 1315-1319.
24. [24] V. Dujols, F. Ford, A.W. Czarnik, A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water, J. Am. Chem. Soc. 119 (1997) 7386-7387.[24] V. Dujols, F. Ford, A.W. Czarnik, A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water, J. Am. Chem. Soc. 119 (1997) 7386-7387.
25. [25] Z.X. Han, B.S. Zhu, T.L. Wu, et al., A fluorescent probe for Hg²⁺ sensing in solutions and living cells with a wide working pH range, Chin. Chem. Lett. 25 (2014) 73-76.[25] Z.X. Han, B.S. Zhu, T.L. Wu, et al., A fluorescent probe for Hg²⁺ sensing in solutions and living cells with a wide working pH range, Chin. Chem. Lett. 25 (2014) 73-76.
26. [26] C. Liu, J. Pan, S. Li, et al., Capture and visualization of hydrogen sulfide by a fluorescent probe, Angew. Chem. Int. Ed. 50 (2011) 10327-10329.[26] C. Liu, J. Pan, S. Li, et al., Capture and visualization of hydrogen sulfide by a fluorescent probe, Angew. Chem. Int. Ed. 50 (2011) 10327-10329.
27. [27] J. Zhang, Y.Q. Sun, J. Liu, Y. Shi, W. Guo, A fluorescent probe for the biological signaling molecule H₂S based on a specific H₂S trap group, Chem. Commun. 49 (2013) 11305-11307.[27] J. Zhang, Y.Q. Sun, J. Liu, Y. Shi, W. Guo, A fluorescent probe for the biological signaling molecule H₂S based on a specific H₂S trap group, Chem. Commun. 49 (2013) 11305-11307.
28. [28] C. Wei, Q. Zhu, W. Liu, et al., NBD-based colorimetric and fluorescent turn-on probes for hydrogen sulfide, Org. Biomol. Chem. 12 (2014) 479-485.[28] C. Wei, Q. Zhu, W. Liu, et al., NBD-based colorimetric and fluorescent turn-on probes for hydrogen sulfide, Org. Biomol. Chem. 12 (2014) 479-485.
29. [29] C. Liu, B. Peng, S. Li, et al., Reaction based fluorescent probes for hydrogen sulfide, Org. Lett. 14 (2012) 2184-2187.[29] C. Liu, B. Peng, S. Li, et al., Reaction based fluorescent probes for hydrogen sulfide, Org. Lett. 14 (2012) 2184-2187.
30. [30] T. Liu, Z. Xu, D.R. Spring, J. Cui, A lysosome-targetable fluorescent probe for imaging hydrogen sulfide in living cells, Org. Lett. 15 (2013) 2310-2313.[30] T. Liu, Z. Xu, D.R. Spring, J. Cui, A lysosome-targetable fluorescent probe for imaging hydrogen sulfide in living cells, Org. Lett. 15 (2013) 2310-2313.
31. [31] T. Liu, X. Zhang, Q. Qiao, et al., A two-photon fluorescent probe for imaging hydrogen sulfide in living cells, Dyes Pigments 99 (2013) 537-542.[31] T. Liu, X. Zhang, Q. Qiao, et al., A two-photon fluorescent probe for imaging hydrogen sulfide in living cells, Dyes Pigments 99 (2013) 537-542.

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