Recent advances in fluorescent probes for the detection of hydrogen sulfide

Current Organic Chemistry

Volumn 17, Issue 6, 2013, Pages 641-653

  Peng, Hanjing ^a   Chen, Weixuan ^a   Burroughs, Sarah ^a   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Cell imaging; Detection methods; Fluorescent probes; Fluorescent sensors; Gasotransmitters; Hydrogen sulfide

Indexed keywords

CARBON MONOXIDE; CARDIOVASCULAR SYSTEM; CHROMATOGRAPHIC ANALYSIS; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; NITRIC OXIDE; PROBES; RESPIRATORY SYSTEM; SULFUR DETERMINATION;

'CURRENT; CELL IMAGING; CENTRAL NERVOUS SYSTEMS; DETECTION METHODS; ENDOCRINE SYSTEMS; FLUORESCENT PROBES; FLUORESCENT SENSORS; GASOTRANSMITTER; GASTROINTESTINAL SYSTEMS; MOLECULAR MECHANISM;

HYDROGEN SULFIDE;

EID: 84877732936     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317060007     Document Type: Review

References (96)

1. Morse, J. W.; Millero, F. J.; Cornwell, J. C.; Rickard, D., The chemistry of the hydrogen sulfide and iron sulfide systems in natural waters. Earth-Sci. Rev. 1987, 24, 1-42.
2. Evans, C. L., The toxicity of hydrogen sulphide and other sulphides. Exp. Physiol. 1967, 52, 231-248.
3. ASTDR Toxicological profile for hydrogen sulfide. Available from: URL http://www.atsdr.cdc.gov/toxprofiles/tp.asp?id=389&tid=67.
4. Judy Strickland; Audrey Cummings; Joseph A. Spinnato III; John J. Liccione; Gary L. Foureman, Toxicological review of hydrogen sulfide. In Agency, U. S. E. P., Ed. Washington, DC, 2003.
5. Reiffenstein, R. J.; Hulbert, W. C.; Roth, S. H., Toxicology of hydrogensulfide. Annu. Rev. Pharmacol. Toxicol. 1992, 32, 109-134.
6. 2S by cystathionine beta-synthase via the condensation of cysteine and homocysteine. J. Biol. Chem. 2004, 279, (50), 52082-52086.
7. Ishii, I.; Akahoshi, N.; Yu, X. N.; Kobayashi, Y.; Namekata, K.; Komaki, G.; Kimura, H., Murine cystathionine gamma-lyase: complete cDNA and genomic sequences, promoter activity, tissue distribution and developmental expression. Biochem. J. 2004, 381, 113-123.
8. Shibuya, N.; Mikami, Y.; Kimura, Y.; Nagahara, N.; Kimura, H., Vascular endothelium expresses 3-mercaptopyruvate sulfurtransferase and produces hydrogen sulfide. J. Biochem. 2009, 146, (5), 623-6.
9. 2S by 3-mercaptopyruvate sulphurtransferase. J. Biochem. 2011, 149, (4), 357-9.
10. Goodwin, L. R.; Francom, D.; Dieken, F. P.; Taylor, J. D.; Warenycia, M. W.; Reiffenstein, R. J.; Dowling, G., Determination of sulfide in brain tissue by gas dialysis/ion chromatography: postmortem studies and two case reports. J. Anal. Toxicol. 1989, 13, 105-109.
11. Warenycia, M. W.; Goodwin, L. R.; Benishin, C. G.; Reiffenstein, R. J.; Francom, D. M.; Taylor, J. D.; Dieken, F. P., Acute hydrogen sulfide poisoning, demonstration of selelective uptake of sulfide by the brainstem by measurement of brain sulfide levels. Biochem. Pharmacol. 1989, 38, (6), 973-981.
12. Richardson, C. J.; Magee, E. A. M.; Cummings, J. H., A new method for the determination of sulphide in gastrointestinal contents and whole blood by microdistillation and ion chromatography. Clin. Chim. Acta 2000, 293, (1-2), 115-125.
13. Boehning, D.; Snyder, S. H., Novel neural modulators. Annu. Rev. Neurosci. 2003, 26, 105-131.
14. 2S be the third endogenous gaseous transmitter? FASEB J. 2002, 16, (13), 1792-1798.
15. Culotta, E.; Koshland, D. E., NO news is good news. Science 1992, 258, (5090), 1862-1865.
16. Morita, T.; Perrella, M. A.; Lee, M. E.; Kourembanas, S., Smooth-muscle cell-derived carbon-monoxide is a regulator of vascular cGMP. P. Natl. Acad. Sci. U. S. A. 1995, 92, (5), 1475-1479.
17. Nicholls, P.; Kim, J.-K., Sulphide as an inhibitor and electron donor for the cytochrome c oxidase system. Can. J. Biochem. 1982, 60, (6), 613-623.
18. Volkel, S.; Grieshaber, M. K., Mitochondrial sulfide oxidation in Arenicola marina-Evidence for alternative electron pathways. Eur. J. Biochem. 1996, 235, (1-2), 231-237.
19. 2S as a physiologic vasorelaxant: Hypertension in mice with deletion of cystathionine gamma-lyase. Science 2008, 322, (5901), 587-590.
20. 2S-induced vasorelaxation and underlying cellular and molecular mechanisms. Am. J. Physiol.-Heart C. 2002, 283, (2), H474-H480.
21. 2S as a novel endogenous gaseous K-ATP channel opener. EMBO J. 2001, 20, (21), 6008-6016.
22. 2S signals through protein S-sulfhydration. Sci. Signal. 2009, 2, (96), ra72.
23. Finkel, T., From sulfenylation to sulfhydration: What a thiolate needs to tolerate. Sci. Signal. 2012, 5, (215).
24. Mustafa, A. K.; Sikka, G.; Gazi, S. K.; Steppan, J.; Jung, S. M.; Bhunia, A. K.; Barodka, V. M.; Gazi, F. K.; Barrow, R. K.; Wang, R.; Amzel, L. M.; Berkowitz, D. E.; Snyder, S. H., Hydrogen sulfide as endothelium-derived hyperpolarizing factor sulfhydrates potassium channels. Circ. Res. 2011, 109, (11), 1259-1268.
25. 2S-induced activation of KATP channels. Antioxid. Redox Sig. 2010, 12, (10), 1167-1178.
26. Kamoun, P.; Belardinelli, M.-C.; Chabli, A.; Lallouchi, K.; Chadefaux-Vekemans, B., Endogenous hydrogen sulfide overproduction in down syndrom. Am. J. Med. Genet. 2003, 116A, (3), 310-311.
27. Chen, Y.-H.; Yao, W.-Z.; Geng, B.; Ding, Y.-L.; Lu, M.; Zhao, M.-W.; Tang, C.-S., Endogenous hydrogen sulfide in patients with COPD. Chest 2005, 128, 3205-3211.
28. Lefer, D. J., A new gaseous signaling molecule emerges: Cardioprotective role of hydrogen sulfide. P. Natl. Acad. Sci. U. S. A. 2007, 104, (46), 17907-17908.
29. Kimura, H., Hydrogen sulfide as a neuromodulator. Mol. Neurobiol. 2002, 26, (1), 13-19.
30. Zhang, L.; Sio, S. W. S.; Moochhala, S.; Bhatia, M., Role of Hydrogen sulfide in severe burn injury-induced inflammation in mice. Mol. Med. 2010, 16, (9-10), 417-424.
31. Li, L.; Bhatia, M.; Zhu, Y. Z.; Zhu, Y. C.; Ramnath, R. D.; Wang, Z. J.; Anuar, F. B. M.; Whiteman, M.; Salto-Tellez, M.; Moore, P. K., Hydrogen sulfide is a novel mediator of lipopolysaccharide-induced inflammation in the mouse. FASEB J. 2005, 19, (6), 1196-1198.
32. Martelli, A.; Testai, L.; Breschi, M. C.; Blandizzi, C.; Virdis, A.; Teddei, S.; Calderone, V., Hydrogen sulfide: novel oppotunity for drug discovery. Med. Res. Rev. 2011.
33. Vandiver, M. S.; Snyder, S. H., Hydrogen sulfide: a gasotransmitter of clinical relevance. J. Mol. Med. 2012, 90, (3), 255-263.
34. Wallace, J. L., Hydrogen sulfide-releasing anti-inflammatory drugs. Trends Pharmacol. Sci. 2007, 28, (10), 501-505.
35. Benavides, G. A.; Squadrito, G. L.; Mills, R. W.; Patel, H. D.; Isbell, T. S.; Patel, R. P.; Darley-Usmar, V. M.; Doeller, J. E.; Kraus, D. W., Hydrogen sulfide mediates the vasoactivity of garlic. P. Natl. Acad. Sci. U. S. A. 2007, 104, (46), 17977-17982.
36. Munchberg, U.; Anwar, A.; Mecklenburg, S.; Jacob, C., Polysulfides as biologically active ingredients of garlic. Org. Biomol. Chem. 2007, 5, (10), 1505-1518.
37. Li, L.; Whiteman, M.; Guan, Y. Y.; Neo, K. L.; Cheng, Y.; Lee, S. W.; Zhao, Y.; Baskar, R.; Tan, C. H.; Moore, P. K., Characterization of a novel, watersoluble hydrogen sulfide-Releasing molecule (GYY4137): New insights into the biology of hydrogen sulfide. Circulation 2008, 117, (18), 2351-2360.
38. 2S-donors. Bioorg. Med. Chem. 2012, 20, (8), 2675-2678.
39. Hyspler, R.; Ticha, A.; Indrova, M.; Zadak, Z.; Hysplerova, L.; Gasparic, J.; Churacek, J., A simple, optimized method for the determination of sulphide in whole blood by GC-MS as a marker of bowel fermentation processes. J. Chromatogr. B 2002, 770, (1-2), 255-259.
40. 2S in patients with coronary heart disease. J. First. Mil. Med. Univ. 2005, 25, 951-954.
41. Savage, J. C.; Gould, D. H., Determination of sulfide in brain tissue and rumen fluid by ion-interaction reversed-phase high-performance liquid chromatography. J. Chromatogr. Biomed. 1990, 526, 540-545.
42. Furne, J.; Saeed, A.; Levitt, M. D., Whole tissue hydrogen sulfide concentrations are orders of magnitude lower than presently accepted values. Am. J. Physiol-Reg. I. 2008, 295, (5), R1479-R1485.
43. 2S/sulfide concentration in vertebrate blood and its potential significance in ischemic preconditioning and vascular signaling. Am. J. Physiol-Reg. I. 2008, 294, (6), R1930-R1937.
44. Grasshoff, K.; Ehrhardt, M.; Kremling, K., Methods of seawater analysis. 3 ed.; Wiley-VCH: New York, 1999.
45. Hill, P. G.; Smith, R. M., Determination of sulphur compounds in beer using headspace solid-phase microextraction and gas chromatographic analysis with pulsed flame photometric detection. J. Chromatogr. A 2000, 872, (1-2), 203-213.
46. Berube, P. R.; Parkinson, P. D.; Hall, E. R., Measurement of reduced sulphur compounds contained in aqueous matrices by direct injection into a gas chromatograph with a flame photometric detector. J. Chromatogr. A 1999, 830, (2), 485-489.
47. Radfordknoery, J.; Cutter, G. A., Determination of carbonyl sulfide and hydrogen sulfide species in natural waters using specialized collection procedures and gas chromatography with flame photometric detection. Anal. Chem. 1993, 65, (8), 976-982.
48. Cutter, G. A.; Oatts, T. J., Determination of dissolved sulfide and sedimentary sulfur speciation using gas chromatography-photoionization detection. Anal. Chem. 1987, 59, 717-721.
49. Mylon, S. E.; Benoit, G., Subnanomolar detection of acid-labile sulfides by the classical methylene blue method coupled to HPLC. Environ. Sci. Technol. 2001, 35, (22), 4544-4548.
50. Searcy, D. G.; Peterson, M. A., Hydrogen sulfide consumption measured at low steady state concentrations using a sulfidostat. Anal. Biochem. 2004, 324, (2), 269-275.
51. Menon, S. K.; Sathyapalan, A.; Agrawal, Y. K., Ion selective electrodes in pharmaceutical analysis-A review. Rev. Anal. Chem. 1997, 16, (4), 333-353.
52. Schiavon, G.; Zotti, G.; Toniolo, R.; Bontempelli, G., Electrochemical detection of trace hydrogen-sulfide in gaseous samples by porous silver electrodes supported on ion-exchange membranes (solid polymer electrolytes). Anal. Chem. 1995, 67, (2), 318-323.
53. Light, T. S.; Swartz, J. L., Analytical evaluation of the silver sulfide membrane electrode. Anal. Chem. 1968, 825-836.
54. Hseu, T.-M.; Rechnitz, G. A., Analytical study of a sulfide ion-selective membrane electrode in alkaline solution. Anal. Chem. 1968, 40, (7), 1054-1060.
55. Canterford, D. R., Direct determination of sulfide by rapid direct current polarography. Anal. Chem. 1973, 45, (14), 2414-2417.
56. Doeller, J. E.; Isbell, T. S.; Benavides, G.; Koenitzer, J.; Patel, H.; Patel, R. P.; Lancaster, J. R.; Darley-Usmar, V. M.; Kraus, D. W., Polarographic measurement of hydrogen sulfide production and consumption by mammalian tissues. Anal. Biochem. 2005, 341, (1), 40-51.
57. Lei, W.; Dasgupta, P. K., Determination of sulfide and mercaptans in caustic scrubbing liquor. Anal. Chim. Acta. 1989, 226, 165-170.
58. Almy, L. H., A method for the estimation of hydrogen sulfide in proteinaceous food products. J. Am. Chem. Soc. 1925, 47, (5), 1381-1390.
59. Cline, J. D., Spectrophotometric determination of hydrogen sulfide in natural waters. Limnol. Oceanogr. 1969, 14, 454-458.
60. Lima, G. F.; Brondi, A. M.; Paiva, A.; Tarley, C. R. T.; de Oliveira, A. F.; Wisniewski, C.; Luccas, P. O., Direct introduction of water sample in multisegmented flow-injection analysis for sulfide determination. Anal. Sci. 2011, 27, (3), 309-313.
61. Fernandez-Suarez, M.; Ting, A. Y., Fluorescent probes for super-resolution imaging in living cells. Nat. Rev. Mol. Cell Bio. 2008, 9, (12), 929-943.
62. Crivat, G.; Taraska, J. W., Imaging proteins inside cells with fluorescent tags. Trends Biotechnol. 2012, 30, (1), 8-16.
63. Qian, Y.; Karpus, J.; Kabil, O.; Zhu, H.-L.; Banerjee, R.; Zhao, J.; He, C., Selective fluorescent probes for live-cell monitoring of sulfide. Nature Comm. 2011, 2, 495.
64. Parker, G. J.; Law, T. L.; Lenoch, F. J.; Bolger, R. E., Development of high throughput screening assays using fluorescence polarization: Nuclear receptor-ligand-binding and kinase/phosphatase assays. J. Biomol. Screen. 2000, 5, (2), 77-88.
65. Hanson, G. T.; Hanson, B. J., Fluorescent probes for cellular assays. Comb. Chem. High T. Scr. 2008, 11, (7), 505-513.
66. Falconer, M.; Smith, F.; Surah-Narwal, S.; Congrave, G.; Liu, Z.; Hayter, P.; Ciaramella, G.; Keighley, W.; Haddock, P.; Waldron, G.; Sewing, A., Highthroughput screening for ion channel modulators. J. Biomol. Screen. 2002, 7, (5), 460-465.
67. Belardetti, F.; Tringham, E.; Eduljee, C.; Jiang, X. P.; Dong, H. H.; Hendricson, A.; Shimizu, Y.; Janke, D. L.; Parker, D.; Mezeyova, J.; Khawaja, A.; Pajouhesh, H.; Fraser, R. A.; Arneric, S. P.; Snutch, T. P., A fluorescence-based high-throughput screening assay for the identification of T-type calcium channel blockers. Assay Drug Dev. Technol. 2009, 7, (3), 266-280.
68. Xuan, W. M.; Sheng, C. Q.; Cao, Y. T.; He, W. H.; Wang, W., Fluorescent probes for the detection of hydrogen sulfide in biological systems. Angew. Chem. Int. Ed. 2012, 51, (10), 2282-2284.
69. Ye, X. Y.; Rubakhin, S. S.; Sweedler, J. V., Detection of nitric oxide in single cells. Analyst 2008, 133, (4), 423-433.
70. Nagano, T.; Yoshimura, T., Bioimaging of nitric oxide. Chem. Rev. 2002, 102, (4), 1235-1269.
71. Liu, C. R.; Pan, J.; Li, S.; Zhao, Y.; Wu, L. Y.; Berkman, C. E.; Whorton, A. R.; Xian, M., Capture and visualization of hydrogen sulfide by a fluorescent probe. Angew. Chem. Int. Ed. 2011, 50, (44), 10327-10329.
72. Liu, C. R.; Peng, B.; Li, S.; Park, C. M.; Whorton, A. R.; Xian, M., Reaction based fluorescent probes for hydrogen sulfide. Org. Lett. 2012, 14, (8), 2184-2187.
73. Qian, Y.; Zhang, L.; Ding, S.; Deng, X.; He, C.; Zhu, H.-L.; Zhao, J., A fluorescent probe for rapid detection of hydrogen sulfide in blood plasma and brain tissues in mice. Chem. Sci. 2012, DOI: 10.1039/C2SC20537H.
74. Lippert, A. R.; New, E. J.; Chang, C. J., Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells. J. Am. Chem. Soc. 2011, 133, (26), 10078-10080.
75. Peng, H.; Cheng, Y.; Dai, C.; Wang, B., A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood. Angew. Chem. Int. Ed. 2011, 50 (41), 9672-9675.
76. Montoya, L. A.; Pluth, M. D., Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells. Chem. Comm. 2012, 48, (39), 4767-4769.
77. Yu, F.; Li, P.; Song, P.; Wang, B.; Zhaoa, J.; Han, K., An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells. Chem. Comm. 2012, 48, 2852-2854.
78. Chen, S.; Chen, Z.-j.; Ren, W.; Ai, H.-w., Reaction-based genetically encoded fluorescent hydrogen sulfide sensors. J. Am. Chem. Soc. 2012, 134, (23), 9589-9592.
79. 2+ complex of dipicolylamine appended fluorescein. Chem. Comm. 2009, (47), 7390-7392.
80. Zhang, R.; Yu, X. J.; Yin, Y. J.; Ye, Z. Q.; Wang, G. L.; Yuan, J. L., Development of a heterobimetallic Ru(II)-Cu(II) complex for highly selective and sensitive luminescence sensing of sulfide anions. Anal. Chim. Acta 2011, 691, (1-2), 83-88.
81. Lou, X. D.; Mu, H. L.; Gong, R.; Fu, E. Q.; Qin, J. G.; Li, Z., Displacement method to develop highly sensitive and selective dual chemosensor towards sulfide anion. Analyst 2011, 136, (4), 684-687.
82. Sasakura, K.; Hanaoka, K.; Shibuya, N.; Mikami, Y.; Kimura, Y.; Komatsu, T.; Ueno, T.; Terai, T.; Kimura, H.; Naganot, T., Development of a highly selective fluorescence probe for hydrogen sulfide. J. Am. Chem. Soc. 2011, 133, (45), 18003-18005.
83. Cao, X. W.; Lin, W. Y.; He, L. W., A Near-infrared fluorescence turn-on sensor for sulfide anions. Org. Lett. 2011, 13, (17), 4716-4719.
84. Hou, F. P.; Cheng, J.; Xi, P. X.; Chen, F. J.; Huang, L.; Xie, G. Q.; Shi, Y. J.; Liu, H. Y.; Bai, D. C.; Zeng, Z. Z., Recognition of copper and hydrogen sulfide in vitro using a fluorescein derivative indicator. Dalton Trans. 2012, 41, (19), 5799-5804.
85. Hou, F. P.; Huang, L.; Xi, P. X.; Cheng, J.; Zhao, X. F.; Xie, G. Q.; Shi, Y. J.; Cheng, F. J.; Yao, X. J.; Bai, D. C.; Zeng, Z. Z., A retrievable and highly selective fluorescent probe for monitoring sulfide and imaging in living cells. Inorg. Chem. 2012, 51, (4), 2454-2460.
86. Jimenez, D.; Martinez-Manez, R.; Sancenon, F.; Ros-Lis, J. V.; Benito, A.; Soto, J., A new chromo-chemodosimeter selective for sulfide anion. J. Am. Chem. Soc., 2003, 125, (30), 9000-9001.
87. Kosower, E. M.; Barak, P.; Dodiuk, H.; Ben-Shoshan, M.; Kanety, H., Synthesis and properties of 4,6-bridged syn-1,5-diazabicyclo[3, 3, 0] octa-3,6-diene-2,8-diones (m-Bridged 9, 10-dioxabimanes). J. Org. Chem. 1981, 46, (8), 1673-1679.
88. Sakhi, A. K.; Blomhoff, R.; Gundersen, T. E., Simultaneous and trace determination of reduced and oxidized glutathione in minute plasma samples using dual mode fluorescence detection and column switching high performance liquid chromatography. J. Chromatogr. A 2007, 1142, (2), 178-184.
89. Chou, S. T.; Ko, L. E.; Yang, C. S., High performance liquid chromatography with fluorimetric detection for the determination of total homocysteine in human plasma: method and clinical applications. Anal. Chim. Acta 2001, 429, (2), 331-336.
90. Kazemi, F.; Kiasat, A. R.; Sayyahi, S., Chemoselective reduction of azides with sodium sulfide hydrate under solvent free conditions. Phosphorus Sulfur Silicon 2004, 179, (9), 1813-1817.
91. Porter, H. K., The zinin reduction of nitroarenes. Org. Reactions, 2011, pp. 455-481.
92. Zinin, N., Beschreibung einiger neuer organischer Basen, dargestellt durch die Einwirkung des Schwefelwasserstoffes auf Verbindungen der Kohlenwasserstoffe mit Untersalpetersäure. J. Prakt. Chem. 1842, 27, (1), 140-153.
93. Liu, C. C.; Schultz, P. G., Adding new chemistries to the genetic code. Annu. Rev. Biochem. 2010, 79, 413-444.
94. Liu, W. S.; Brock, A.; Chen, S.; Chen, S. B.; Schultz, P. G., Genetic incorporation of unnatural amino acids into proteins in mammalian cells. Nat. Methods 2007, 4, (3), 239-244.
95. Sawa, M.; Hsu, T. L.; Itoh, T.; Sugiyama, M.; Hanson, S. R.; Vogt, P. K.; Wong, C. H., Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo. P. Natl. Acad. Sci. U. S. A. 2006, 103, (33), 12371-12376.
96. Koike, T.; Watanabe, T.; Aoki, S.; Kimura, E.; Shiro, M., A novel biomimetic zinc(II)-fluorophore, dansylamidoethyl-pendant macrocyclic tetraamine 1,4,7,10-tetraazacyclododecane (cyclen). J. Am. Chem. Soc. 1996, 118, (50), 12696-12703.