Azide-based fluorescent probes: Imaging hydrogen sulfide in living systems

Methods in Enzymology

Volumn 554, Issue , 2015, Pages 63-80

  Lin, Vivian S ^a   Lippert, Alexander R ^b   Chang, Christopher J ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b SOUTHERN METHODIST UNIVERSITY   (United States)

^c HOWARD HUGHES MEDICAL INSTITUTE   (United States)

Author keywords

Azide reduction; Fluorescence; Hydrogen sulfide; Microscopy; Reaction based sensing; Redox biology

Indexed keywords

AMINE; AZIDE; FLUORESCENT DYE; HYDROGEN SULFIDE; VASCULOTROPIN A;

ARTICLE; BIOCOMPATIBILITY; CONFOCAL MICROSCOPE; CONFOCAL MICROSCOPY; CROSS REACTION; DATA ANALYSIS; DATA PROCESSING; FLUORESCENCE; IN VITRO STUDY; PHOTOACTIVATION; PRIORITY JOURNAL; SAFETY; SPECTROFLUOROMETRY; SYNTHESIS; UMBILICAL VEIN ENDOTHELIAL CELL; CELL CULTURE; CHEMISTRY; CULTURE TECHNIQUE; FLUORESCENCE MICROSCOPY; HUMAN; METABOLISM; STAINING;

MAMMALIA;

AZIDES; CELL CULTURE TECHNIQUES; CELLS, CULTURED; FLUORESCENT DYES; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; HYDROGEN SULFIDE; MICROSCOPY, FLUORESCENCE; STAINING AND LABELING; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 84923536991     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/bs.mie.2014.11.011     Document Type: Chapter

References (46)

1. K. Abe, and H. Kimura The possible role of hydrogen sulfide as an endogenous neuromodulator The Journal of Neuroscience 16 1996 1066 1071
2. 2S production in Parkinson's disease gene knockout astrocytes Journal of the American Chemical Society 135 2013 9915 9923
3. 2S over biological thiols Journal of the American Chemical Society 135 2013 16697 16704
4. J. Chan, S.C. Dodani, and C.J. Chang Reaction-based small-molecule fluorescent probes for chemoselective bioimaging Nature Chemistry 4 2012 973 984
5. 2S) metabolism and its regulatory role in energy production Proceedings of the National Academy of Sciences of the United States of America 109 2012 2943 2948
6. K. Grice, C. Cao, G.D. Love, M.E. Böttcher, R.J. Twitchett, and E. Grosjean Photic zone euxinia during the Permian-triassic superanoxic event Science 307 2005 706 709
7. T.L. Guidotti Hydrogen sulfide: Advances in understanding human toxicity International Journal of Toxicology 29 2010 569 581
8. J. Huang, S. Kumar, N. Abbassi-Ghadi, P. Španěl, D. Smith, and G.B. Hanna Selected ion flow tube mass spectrometry analysis of volatile metabolites in urine headspace for the profiling of gastro-esophageal cancer Analytical Chemistry 85 2013 3409 3416
9. T. Ida, T. Sawa, H. Ihara, Y. Tsuchiya, Y. Watanabe, and Y. Kumagai Reactive cysteine persulfides and S-polythiolation regulate oxidative stress and redox signaling Proceedings of the National Academy of Sciences of the United States of America 111 2014 7606 7611 10.1073/pnas.1321232111
10. P. Kamoun, M.C. Belardinelli, A. Chabli, B. Lallouchi, and B. Chadefaux-Vekemans Endogenous hydrogen sulfide overproduction in Down syndrome American Journal of Medical Genetics. Part A 116A 2003 310 311
11. H. Kimura Hydrogen sulfide: From brain to gut Antioxidants & Redox Signaling 12 2010 1111 1123
12. H. Kimura Hydrogen sulfide: Its production and functions Experimental Physiology 96 2011 833 835
13. Y. Kimura, and H. Kimura Hydrogen sulfide protects neurons from oxidative stress The FASEB Journal 18 2004 1165 1167
14. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: Diverse chemical function from a few good reactions Angewandte Chemie International Edition in English 40 2001 2004 2021
15. M. Lee, C. Schwab, S. Yu, E. McGeer, and P.L. McGeer Astrocytes produce the antiinflammatory and neuroprotective agent hydrogen sulfide Neurobiology of Aging 30 2009 1523 1534
16. L. Li, P. Rose, and P.K. Moore Hydrogen sulfide and cell signaling Annual Review of Pharmacology and Toxicology 51 2011 169 187
17. V.S. Lin, and C.J. Chang Fluorescent probes for sensing and imaging biological hydrogen sulfide Current Opinion in Chemical Biology 16 2012 595 601
18. 2S production Proceedings of the National Academy of Sciences of the United States of America 110 2013 7131 7135
19. A.R. Lippert Designing reaction-based fluorescent probes for selective hydrogen sulfide detection Journal of Inorganic Biochemistry 133 2014 136 142
20. A.R. Lippert, E.J. New, and C.J. Chang Reaction-based fluorescent probes for the selective imaging of hydrogen sulfide in living cells Journal of the American Chemical Society 133 2011 10078 10080
21. A.R. Lippert, G.C. Van de Bittner, and C.J. Chang Boronate oxidation as a bioorthogonal reaction approach for studying the chemistry of hydrogen peroxide in living systems Accounts of Chemical Research 44 2011 793 804
22. C. Liu, W. Chen, W. Shi, B. Peng, Y. Zhao, and H. Ma Rational design and bioimaging applications of highly selective fluorescence probes for hydrogen polysulfides Journal of the American Chemical Society 136 2014 7257 7260
23. 2S: Fast response and high selectivity Chemistry: A European Journal 19 2013 4717 4722
24. T. Liu, Z. Xu, D.R. Spring, and J. Cui A lysosome-targetable fluorescent probe for imaging hydrogen sulfide in living cells Organic Letters 15 2013 2310 2313
25. D.L. Miller, and M.B. Roth Hydrogen sulfide increases thermotolerance and lifespan in Caenorhabditis elegans Proceedings of the National Academy of Sciences of the United States of America 104 2007 20618 20622
26. A. Minta, J.P. Kao, and R.Y. Tsien Fluorescent indicators for cytosolic calcium based on rhodamine and fluorescein chromophores The Journal of Biological Chemistry 264 1989 8171 8178
27. K.M. Miranda, and D.A. Wink Persulfides and the cellular thiol landscape Proceedings of the National Academy of Sciences of the United States of America 111 2014 7505 7506
28. K.R. Olson, E.R. DeLeon, and F. Liu Controversies and conundrums in hydrogen sulfide biology Nitric Oxide 41 2014 11 26 10.1016/j.niox.2014.05.012
29. A. Papapetropoulos, A. Pyriochou, Z. Altaany, G. Yang, A. Marazioti, and Z. Zhou Hydrogen sulfide is an endogenous stimulator of angiogenesis Proceedings of the National Academy of Sciences of the United States of America 106 2009 21972 21977
30. A. Papapetropoulos, M. Whiteman, and C. Giuseppe Pharmacological tools for hydrogen sulfide research: A brief, introductory guide for beginners British Journal of Pharmacology 2014 10.1111/bph.12806 early view
31. 2S-rich spark discharge experiment Proceedings of the National Academy of Sciences of the United States of America 108 2011 5526 5531
32. B.D. Paul, J.I. Sbodio, R. Xu, M.S. Vandiver, J.Y. Cha, and A.M. Snowman Cystathionine γ-lyase deficiency mediates neurodegeneration in Huntington's disease Nature 509 2014 96 100
33. H. Peng, Y. Cheng, C. Dai, A.L. King, B.L. Predmore, and D.J. Lefer A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood Angewandte Chemie International Edition in English 50 2011 9672 9675
34. B. Peng, and M. Xian Fluorescent probes for hydrogen sulfide detection Asian Journal of Organic Chemistry 3 2014 914 924
35. J.A. Prescher, and C.R. Bertozzi Chemistry in living systems Nature Chemical Biology 1 2005 13 21
36. N. Shibuya, M. Tanaka, M. Yoshida, Y. Ogasawara, T. Togawa, and K. Ishii 3-Mercaptopyruvate sulfurtransferase produces hydrogen sulfide and bound sulfane sulfur in the brain Antioxidants & Redox Signaling 11 2009 703 714
37. 2S biogenesis via alternative transsulfuration reactions The Journal of Biological Chemistry 284 2009 22457 22466
38. M.H. Stipnauk, and P.W. Beck Characterization of the enzymic capacity for cysteine desulphhydration in liver and kidney of rat The Biochemical Journal 206 1982 267 277
39. C. Szabó, C. Coletta, C. Chao, K. Módis, B. Szczesny, and A. Papapetropoulos Tumor-derived hydrogen sulfide, produced by cystathionine-β-synthase, stimulates bioenergetics, cell proliferation, and angiogenesis in colon cancer Proceedings of the National Academy of Sciences of the United States of America 110 2013 12474 12479
40. M. Vandiver, and S.H. Snyder Hydrogen sulfide: A gasotransmitter of clinical relevance Journal of Molecular Medicine 90 2012 255 263
41. Q. Wan, Y. Song, Z. Li, X. Gao, and H. Ma In vivo monitoring of hydrogen sulfide using cresyl violet-based ratiometric fluorescence probe Chemical Communications 49 2013 502 504
42. 2S and suppressed insulin release in Zucker diabetic rats Laboratory Investigation 89 2009 59 67
43. 2S as a physiologic vasorelaxant: Hypertension in mice with deletion of cystathionine γ-lyase Science 322 2008 587 590
44. F. Yu, X. Han, and L. Chen Fluorescent probes for hydrogen sulfide detection and bioimaging Chemical Communications 50 2014 12234 12249
45. F. Yu, P. Li, P. Song, B. Wang, J. Zhao, and K. Han An ICT-based strategy to colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells Chemical Communications 48 2012 2852 2854
46. 2S-induced vasorelaxation and underlying cellular and molecular mechanisms American Journal of Physiology. Heart and Circulatory Physiology 283 2002 H474 H480