A colorimetric and ratiometric fluorescent probe with a large stokes shift for detection of hydrogen sulfide

Dyes and Pigments

Volumn 123, Issue , 2015, Pages 78-84

  Xiang, Kaiqiang ^a   Liu, Yunchang ^a   Li, Changjiang ^b   Tian, Baozhu ^a   Tong, Tianzhong ^a   Zhang, Jinlong ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b HUANGSHAN UNIVERSITY   (China)

Author keywords

Fluorescence probe; Hydrogen sulfide; Isophorone; Ratiometric detection; Selectivity; Stokes shift

Indexed keywords

BIOLOGY; CATALYST SELECTIVITY; COLORIMETRY; FLUORESCENCE; FLUOROPHORES; PROBES; SULFUR COMPOUNDS; SULFUR DETERMINATION;

ENVIRONMENTAL TOXINS; FLUORESCENCE PROBES; ISOPHORONES; PATHOLOGICAL PROCESS; QUANTITATIVE DETECTION; RATIOMETRIC DETECTION; SIGNALING MOLECULES; STOKES SHIFT;

HYDROGEN SULFIDE;

EID: 84938854648     PISSN: 01437208     EISSN: 18733743     Source Type: Journal    
DOI: 10.1016/j.dyepig.2015.06.037     Document Type: Article

References (59)

1. F.B. Yu, P. Li, P. Song, B.S. Wang, J.Z. Zhao, and K.L. Han An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells Chem Commun 48 2012 2852 2854
2. F. Zhang, A.W. Zhu, Y.P. Luo, Y. Tian, J.H. Yang, and Y. Qin CuO nanosheets for sensitive and selective determination of H2S with high recovery ability J Phys Chem C 114 2010 19214 19219
3. Y.Y. Guo, T. Zeng, G.Q. Shi, Y.Q. Cai, and R.L. Xie Highly selective naphthalimide-based fluorescent probe for direct hydrogen sulfide detection in the environment RSC Adv 4 2014 33626 33628
4. K. Yao, D. Caruntu, Z.M. Zeng, J.J. Chen, C.J. O'Connor, and W.L. Zhou Parts per billion-level H2S detection at room temperature based on self-assembled In2O3 nanoparticles J Phys Chem C 113 2009 14812 14817
5. C.R. Liu, W. Chen, W. Shi, B. Peng, Y. Zhao, H.M. Ma, and et al. Rational design and bioimaging applications of highly selective fluorescence probes for hydrogen polysulfides J Am Chem Soc 136 2014 7257 7260
6. C.Y. Liu, H.F. Wu, B.J. Han, B.C. Zhu, and X.L. Zhang A highly selective fluorescent chemodosimeter for imaging hydrogen sulfide in living cells Dyes Pigments 110 2014 214 218
7. B.D. Paul, and S.H. Snyder H2S signalling through protein sulfhydration and beyond Nat Rev Mol Cell Biol 13 2012 499 507
8. J.M. Fukuto, S.J. Carrington, D.J. Tantillo, J.G. Harrison, L.J. Ignarro, B.A. Freeman, and et al. Small molecule signaling agents: the integrated chemistry and biochemistry of nitrogen oxides, oxides of carbon, dioxygen, hydrogen sulfide, and their derived species Chem Res Toxicol 25 2012 769 793
9. A. Papapetropoulos, A. Pyriochou, Z. Altaany, G.D. Yang, A. Marazioti, Z.M. Zhou, and et al. Hydrogen sulfide is an endogenous stimulator of angiogenesis Proc Natl Acad Sci U S A 106 2009 21972 21977
10. G.D. Yang, L.Y. Wu, B. Jiang, W. Yang, J.S. Qi, K. Cao, and et al. H2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine γ-lyase Science 322 2008 587 590
11. G.D. Yang, L.Y. Wu, and R. Wang Pro-apoptotic effect of endogenous H2S on human aorta smooth muscle cells FASEB J 20 2006 553 555
12. L. Li, M. Bhatia, and P.K. Moore Hydrogen sulphide - a novel mediator of inflammation? Curr Opin Pharmacol 6 2006 125 129
13. K. Eto, M. Ogasawara, K. Umemura, Y. Nagai, and H. Kimura Hydrogen sulfide is produced in response to neuronal excitation J Neurosci 22 9 2002 3386 3391
14. K. Etoa, T. Asadab, K. Arimab, T. Makifuchic, and H. Kimura Brain hydrogen sulfide is severely decreased in Alzheimer's disease Biochem Biophys Res Commun 293 2002 1485 1488
15. P. Kamoun, M.-C. Belardinelli, A. Chabli, K. Lallouchi, and B. Chadefaux-Vekemans Endogenous hydrogen sulfide overproduction in Down syndrome Am J Med Genet A 116 2003 310 311
16. S. Fiorucci1, E. Antonelli1, A. Mencarelli, S. Orlandi, B. Renga, G. Rizzo, and 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
17. S.K. Bae, C.H. Heo, D.J. Choi, D. Sen, E.-H. Joe, B.R. Cho, and et al. A ratiometric two-photon fluorescent probe reveals reduction in mitochondrial H2S production in Parkinson's disease gene knockout astrocytes J Am Chem Soc 135 2013 9915 9923
18. F.B. Yu, X.Y. Han, and L.X. Chen Fluorescent probes for hydrogen sulfide detection and bioimaging Chem Commun 50 2014 12234 12249
19. J. Yin, Y. Kwon, D. Kim, D. Lee, G. Kim, Y. Hu, and et al. Cyanine-based fluorescent probe for highly selective detection of glutathione in cell cultures and live mouse tissues J Am Chem Soc 136 14 2014 5351 5358
20. M. Gao, R. Wang, F.B. Yu, J.M. You, and L.X. Chen A near-infrared fluorescent probe for the detection of hydrogen polysulfides biosynthetic pathways in living cells and in vivo Analyst 140 2015 3766 3772
21. A.R. Lippert, E.J. New, and C.J. Chang Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells J Am Chem Soc 133 2011 10078 10080
22. H.J. Peng, Y.F. Cheng, C.F. Dai, A.L.B. King, L. Predmore, D.J. Lefer, and et al. A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood Angew Chem Int Ed 50 2011 9672 9675
23. L.A. Montoya, and M.D. Pluth Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells Chem Commun 48 2012 4767 4769
24. S. Chen, Z.-J. Chen, W. Ren, and H.-W. Ai Reaction-based genetically encoded fluorescent hydrogen sulfide sensors J Am Chem Soc 134 2012 9589 9592
25. R. Wang, F.B. Yu, L.X. Chen, H. Chen, L.J. Wang, and W.W. Zhang A highly selective turn-on near-infrared fluorescent probe for hydrogen sulfide detection and imaging in living cells Chem Commun 48 2012 11757 11759
26. L. Zhang, W.Q. Meng, L. Lu, Y.S. Xue, C. Li, F. Zou, and et al. Selective detection of endogenous H2S in living cells and the mouse hippocampus using a ratiometric fluorescent probe Sci Rep 4 2014 5870 5879
27. B.S. Wang, P. Li, F.B. Yu, P. Song, X.F. Sun, S.Q. Yang, and et al. A reversible fluorescence probe based on Se-BODIPY for the redox cycle between HClO oxidative stress and H2S repair in living cells Chem Commun 49 2013 1014 1016
28. Z.R. Lou, P. Li, Q. Pan, and K.L. Han A reversible fluorescent probe for detecting hypochloric acid in living cells and animals: utilizing a novel strategy for effectively modulating the fluorescence of selenide and selenoxide Chem Commun 49 2013 2445 2447
29. Y. Qian, J. Karpus, O. Kabil, S.Y. Zhang, H.L. Zhu, R. Banerjee, and et al. Selective fluorescent probes for live-cell monitoring of sulphide Nat Commun 2 2011 495 501
30. X. Li, J. Cheng, Y.L. Gong, B. Yang, and Y.Z. Hu Mapping hydrogen sulfide in rats with a novel azo-based fluorescent probe Biosens Bioelectron 65 2015 302 306
31. C.R. Liu, B. Peng, S. Li, C.M. Park, A.R. Whorton, and M. Xia Reaction based fluorescent probes for hydrogen sulfide Org Lett 14 2012 2184 2187
32. J. Liu, Y.Q. Sun, J.Y. Zhang, T. Yang, J.B. Cao, L.S. Zhang, and et al. A ratiometric fluorescent probe for biological signaling molecule H2S: fast response and high selectivity Chem Eur J 19 2013 4717 4722
33. T.Y. Liu, X.F. Zhang, Q.L. Qiao, C.Y. Zou, L. Feng, J.N. Cui, and et al. A two-photon fluorescent probe for imaging hydrogen sulfide in living cells Dyes Pigments 99 2013 537 542
34. X.W. Cao, W.Y. Lin, and L.W. He A near-infrared fluorescence turn-on sensor for sulfide anions Org Lett 13 2011 4716 4719
35. K. Sasakura, K. Hanaoka, N. Shibuya, Y. Mikami, Y. Kimura, T. Komatsu, and et al. Development of a highly selective fluorescence probe for hydrogen sulfide J Am Chem Soc 133 2011 18003 18005
36. M.Q. Wang, K. Li, J.T. Hou, M.Y. Wu, Z. Huang, and X.Q. Yu BINOL-based fluorescent sensor for recognition of Cu(II) and sulfide anion in water J Org Chem 77 2012 8350 8354
37. S.G. Sun, B. Qiao, N. Jiang, J.T. Wang, S. Zhang, and X.J. Peng Naphthylamine-rhodamine-based ratiometric fluorescent probe for the determination of Pd2+ ions Org Lett 16 2014 1132 1135
38. J.Y. Wang, F.L. Song, J.Y. Wang, and X.J. Peng A near-infrared and ratiometric fluorescent chemosensor for palladium Analyst 138 2013 3667 3672
39. Z.Q. Guo, S.W. Nam, S. Park, and J.Y. Yoon A highly selective ratiometric near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging Chem Sci 3 2012 2760 2765
40. X.H. Wang, Z.Q. Guo, S.Q. Zhu, H. Tian, and W.H. Zhu A naked-eye and ratiometric near-infrared probe for palladium via modulating π-conjugated system of cyanines Chem Commun 50 2014 13525 13528
41. X. Wang, J. Sun, W.H. Zhang, X.X. Ma, J.Z. Lv, and B. Tang A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells Chem Sci 4 2013 2551 2556
42. S.Z. Pu, L.L. Ma, G. Liu, H.C. Ding, and B. Chen A multiple switching diarylethene with a phenyl-linked rhodamine B unit and its application as chemosensor for Cu2+ Dyes Pigments 113 2015 70 77
43. P. Hou, S. Chen, H.B. Wang, J.X. Wang, K. Voitchovsky, and X.Z. Song An aqueous red emitting fluorescent fluoride sensing probe exhibiting a large Stokes shift and its application in cell imaging Chem Commun 50 2014 320 322
44. X.M. Wu, X.R. Sun, Z.Q. Guo, J.B. Tang, Y.Q. Shen, T.D. James, and et al. In vivo and in situ tracking cancer chemotherapy by highly photostable NIR fluorescent theranostic prodrug J Am Chem Soc 136 2014 3579 3588
45. P. Liu, X.T. Jing, F.B. Yu, C.J. Lv, and L.X. Chen A near-infrared fluorescent probe for the selective detection of HNO in living cells and in vivo Analyst 140 2015 4576 4583
46. M. Gao, F.B. Yu, H. Chen, and L.X. Chen A near-infrared fluorescent probe for imaging mitochondrial hydrogen polysulfides in living cells and in vivo Anal Chem 87 2015 3631 3638
47. X.T. Jing, F.B. Yu, and L.X. Chen Visualization of nitroxyl (HNO) in vivo via a lysosome-targetable near-infrared fluorescent probe Chem Commun 50 2014 14253 14256
48. B. Liu, W.H. Zhu, Q. Zhang, W.J. Wu, M. Xu, Z.J. Ning, and et al. Conveniently synthesized isophorone dyes for high efficiency dye-sensitized solar cells: tuning photovoltaic performance by structural modification of donor group in donor-π-acceptor system Chem Commun 13 2009 1766 1768
49. Z.J. Ning, Q. Zhang, W.J. Wu, H.C. Pei, B. Liu, and H. Tian Starburst triarylamine based dyes for efficient dye-sensitized solar cells J Org Chem 73 2008 3791 3797
50. O.-P. Kwon, S.-J. Kwon, M. Jazbinsek, F.D.J. Brunner, J.-I. Seo, C. Hunziker, and et al. Organic phenolic configurationally locked polyene single crystals for electro-optic and terahertz wave applications Adv Funct Mater 18 2008 3242 3250
51. O.-P. Kwon, B. Ruiz, A. Choubey, L. Mutter, A. Schneider, M. Jazbinsek, and et al. Organic nonlinear optical crystals based on configurationally locked polyene for melt growth Chem Mater 18 17 2006 4049 4054
52. Z.Q. Guo, W.H. Zhu, and H. Tian Dicyanomethylene-4H-pyran chromophores for OLED emitters, logic gates and optical chemosensors Chem Commun 48 2012 6073 6084
53. Y.-W. Duan, X.-F. Yang, Y.G. Zhong, Y. Guo, Z. Li, and H. Li A ratiometric fluorescent probe for gasotransmitter hydrogen sulfide based on a coumarin-benzopyrylium platform Anal Chim Acta 859 2015 59 65
54. Y. Jiang, Q. Wu, and X.J. Chang A ratiometric fluorescent probe for hydrogen sulfide imaging in living cells Talanta 121 2014 122 126
55. W. Sun, J.L. Fan, C. Hu, J.F. Cao, H. Zhang, X.Q. Xiong, and et al. A two-photon fluorescent probe with near-infrared emission for hydrogen sulfide imaging in biosystems Chem Commun 49 2013 3890 3892
56. G.J. Mao, T.T. Wei, X.X. Wang, S.Y. Huan, D.Q. Lu, J. Zhang, and et al. High-sensitivity naphthalene-based two-photon fluorescent probe suitable for direct bioimaging of H2S in living cells Anal Chem 85 2013 7875 7881
57. Q.Q. Wan, Y.C. Song, Z. Li, X.H. Gao, and H.M. Ma In vivo monitoring of hydrogen sulfide using a cresyl violet-based ratiometric fluorescence probe Chem Commun 49 2013 502 504
58. J. Zhou, Y.Y. Luo, Q. Li, J.N. Shen, R. Wang, Y.F. Xu, and et al. Assembly of indole fluorophore in situ for hydrogen sulfide signaling through substrate triggered intramolecular reduction-cyclization cascade: a sensitive and selective probe in aqueous solution New J Chem 38 2014 2770 2773
59. K. Gorska, A. Manicardi, S. Barluenga, and N. Winssinger DNA-templated release of functional molecules with azide-reduction-triggered immolative linker Chem Commun 47 2011 4364 4366