Highly selective fluorescent and colorimetric probe for live-cell monitoring of sulphide based on bioorthogonal reaction

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Huo, Fang Jun ^a   Kang, Jin ^a   Yin, Caixia ^a   Chao, Jianbin ^a   Zhang, Yongbin ^a  

^a SHANXI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84924678262     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep08969     Document Type: Article

References (53)

1. Sletten, E.M. & Bertozzi, C. R. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew. Chem. Int. Ed. 48, 6974-6978 (2011).
2. Le Droumaguet, C. et al. Fluorogenic click reaction. Chem. Soc. Rev. 39, 1233-1239 (2010).
3. Best, M. D. Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules. Biochem. 48, 6571-6584 (2009).
4. Jewett, J. C. & Bertozzi, C. R. Cu-free click cycloaddition reactions in chemical biology. Chem. Soc. Rev. 39, 1272-1279 (2010).
5. Best, M. D. Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules. Biochem. 48, 6571-6584 (2009).
6. Sivakumar, K. et al. Fluorogenic 1, 3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes. Org. Lett. 6, 4603-4606 (2004).
7. Xie, F. et al. A fluorogenic 'click' reaction of azidoanthracene derivatives. Tetrahedron 64, 2906-2914 (2008).
8. Wang, C. et al. Tuning the optical properties of BODIPY dye through Cu (I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Sci. China Chem. 55, 125-130 (2012).
9. Sawa, M. et al. Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivoProc. Natl. Acad. Sci. U.S.A. 103, 12371-12376 (2006).
10. Zhou, Z. & Fahrni, C. J. A. Fluorogenic Probe for the Copper (I)-Catalyzed Azide - Alkyne Ligation Reaction:Modulation of the Fluorescence Emission via 3(n,π∗)21(π,π∗) Inversion. J. Am. Chem. Soc. 126, 8862-8863 (2004).
11. Key, J. A. & Cairo, C. W. Identification of fluorogenic and quenched benzoxadiazole reactive chromophores. Dyes Pigm. 88, 95-102 (2010).
12. Qi, J. et al. Developing Visible Fluorogenic 'Click-On' Dyes for Cellular Imaging. Bioconjugate Chem. 22, 1758-1762 (2011).
13. Weissleder, R. & Ntziachristos, V. Shedding light onto live molecular targets. Nat. Med. 9, 123-128 (2003).
14. Li, J. et al. Rapid Synthesis, Screening, and Identification of Xanthone- and Xanthene-Based Fluorophores Using Click Chemistry. Org. Lett. 11, 3008-3011 (2009).
15. Shieh, P. et al. Fluorogenic Azidofluoresceins for Biological Imaging. J. Am. Chem. Soc. 134, 17428-17431 (2012).
16. Qian, Y. et al. Selective fluorescent probes for live-cell monitoring of sulphide. Nat. Commun. 2, 1506-1512 (2011).
17. Chen, W. et al. New fluorescent probes for sulfane sulfurs and the application in bioimaging. Chem. Sci. 4, 2892-2896 (2013).
18. Papapetropoulos, A. et al. Hydrogen sulfide is an endogenous stimulator of angiogenesis. Proc. Natl. Acad. Sci. U.S.A. 106, 21972-21977 (2009).
19. 2S as a Physiologic Vasorelaxant: Hypertension in Mice with Deletion of Cystathionine γ-Lyase. Science 322, 587-590 (2008).
20. Yang, G. et al. Pro-apoptotic effect of endogenous H2S on human aorta smooth muscle cells. FASEB J. 20, 553-555 (2006).
21. Li, L. et al. Hydrogen sulfide is a novel mediator of lipopolysaccharide-induced inflammation in the mouse. FASEB J. 19, 1196-1198 (2005).
22. Abe, K. & Kimura, H. The possible role of hydrogen sulfide as an endogenous neuromodulator. J. Neurosci. 16, 1066-1071 (1996).
23. Eto, K. et al. Brain hydrogen sulfide is severely decreased in alzheimer's disease. Biochem. Biophys. Res. Commun. 293, 1485-1488 (2002).
24. Kamoun, P. et al. Endogenous hydrogen sulfide overproduction in Down syndrome. Am. J. Med. Genet. 116A, 310-311 (2003).
25. 2S in rat insulin-secreting cells and the underlying mechanisms. J. Physiol. 569, 519-531 (2005).
26. 2S regulates perfusion pressure in both the isolated and perfused normal rat liver and in cirrhosis. J. Hepatol. 42, 539-548 (2005).
27. Liu, Y. & Feng, G. A visible light excitable colorimetric and fluorescent ESIPT probe for rapid and selective detection of hydrogen sulfide. Org. Biomol. Chem. 12, 438-445 (2014).
28. Peng, H. et al. A Fluorescent Probe for Fast and Quantitative Detection of Hydrogen Sulfide in Blood. Angew. Chem. Int. Ed. 50, 9672-9675 (2011).
29. Montoya, L. A. & Pluth, M. D. Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells. Chem. Commun. 48, 4767-4769 (2012).
30. Das, S. et al. A small molecule two-photon probe for hydrogen sulfide in live tissues. Chem. Commun. 48, 8395-8397 (2012).
31. Chen, S. et al. Reaction-Based Genetically Encoded Fluorescent Hydrogen Sulfide Sensors. J. Am. Chem. Soc. 134, 9589-9592 (2012).
32. Lippert, A. R. et al. Reaction-Based Fluorescent Probes for Selective Imaging of Hydrogen Sulfide in Living Cells. J. Am. Chem. Soc. 133, 10078-11080 (2011).
33. Yu, F. et al. An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells. Chem. Commun. 48, 2852-2854 (2012).
34. Wan, Q. et al. In vivo monitoring of hydrogen sulfide using a cresyl violet-based ratiometric fluorescence probe. Chem. Commun. 49, 502-504 (2013).
35. Yu, F. et al. An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells. Chem. Commun. 48, 2852-2854 (2012).
36. Sun, K., Liu, X., Wang, Y. &Wu, Z. A polymer-based turn-on fluorescent sensor for specific detection of hydrogen sulfide. RSC Adv. 3, 14543-14548 (2013).
37. Jiang, Y.,Wu, Q.&Chang, X.Aratiometric fluorescent probe for hydrogen sulfide imaging in living cells. Talanta 121, 122-126 (2014).
38. Sun, W. et al. A two-photon fluorescent probe with near-infrared emission for hydrogen sulfide imaging in biosystems. Chem. Commun. 49, 3890-3892 (2013).
39. 2S over Biological Thiols. J. Am. Chem. Soc. 135, 16697-16704 (2013).
40. 2+ Probes. J. Org. Chem. 78, 5328-5338 (2013).
41. Xuan, W. et al. Fluorescent Probes for the Detection of Hydrogen Sulfide in Biological Systems. Angew. Chem. Int. Ed. 51, 2282-2284 (2012).
42. Zhang, L. et al.Acolorimetric and ratiometric fluorescent probe for the imaging of endogenous hydrogen sulphide in living cells and sulphide determination in mouse hippocampus. Org. Biomol. Chem. 12, 5115-5125 (2014).
43. Wolfe, S. K., Andrade, C. & Swinehart, J. H. Kinetic studies of the pentacyanonitrosylferrate(2-) azide and hydroxylamine reactions. Inorg. Chem. 13, 2567-2572 (1974).
44. Yi, L. et al. A highly sensitive fluorescence probe for fast thiol-quantification assay of glutathione reductase. Angew. Chem. Int. Ed. Engl. 48, 4034-4037 (2009).
45. Que, E. L., Domaille, D. W. & Chang, C. J. Metals in neurobiology: probing their chemistry and biology with molecular imaging. Chem. Rev. 108, 1517-1549 (2008).
46. Chen, S., Chen, Z.-J., Ren, W. & Ai, H.-W. Reaction-Based Genetically Encoded Fluorescent Hydrogen Sulfide Sensors. J. Am. Chem. Soc. 134, 9589 (2012).
47. Cao, X., Lin, W., Zheng, K. &He, L. A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether. Chem. Commun. 48, 10529-10531 (2012).
48. Yang, X. F., Wang, L., Xu, H. M. & Zhao, M. L. A fluorescein-based fluorogenic and chromogenic chemodosimeter for the sensitive detection of sulfide anion in aqueous solution. Anal. Chim. Acta 631, 91-95 (2009).
49. Fu, L. et al. A ratiometric "two-in-one" fluorescent chemodosimeter for fluoride and hydrogen sulfide. Sens. Actuators B 193, 701-707 (2014).
50. 2+ ensemble based colorimetric probe toward hydrogen sulfide in aqueous media. Tetrahedron Lett. 52, 5000-5003 (2011).
51. Zhang, D.&Jin, W. Highly selective and sensitive colorimetric probe for hydrogen sulfide by a copper (II) complex of azo-dye based on chemosensing ensemble approach. Spectrochimica Acta Part A 90, 35-39 (2012).
52. Qian, Y. et al. A fluorescent probe for rapid detection of hydrogen sulfide in blood plasma and brain tissues in mice. Chem. Sci. 3, 2920-2923 (2012).
53. Wang, X. et al. A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells. Chem. Sci. 4, 2551-2556 (2013).