Recent advances in fluorescent probes for monitoring of hydrogen sulfide

Current Medicinal Chemistry

Volumn 20, Issue 23, 2013, Pages 2929-2937

  Duan, Cun Xian ^a   Liu, Yu Guo ^a  

^a SHANDONG CANCER HOSPITAL AND INSTITUTE   (China)

Author keywords

Fluorescent probes; Hydrogen sulfide; Reactive sulfur species

Indexed keywords

AZIDE; COPPER ION; CYCLAM; CYSTATHIONINE BETA SYNTHASE; DITHIOTHREITOL; FLUORESCENT DYE; HYDROGEN SULFIDE; MERCAPTOETHANOL; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; REACTIVE SULFUR SPECIES; ZINC ION;

AQUEOUS SOLUTION; ARTICLE; BIOGENESIS; BIOLOGICAL MONITORING; BIOLOGY; CHEMICAL STRUCTURE; DISULFIDE BOND; ELECTRON; FLUORESCENCE; IN VITRO STUDY; MICHAEL ADDITION; NONHUMAN; NUCLEOPHILICITY; PH; REACTION ANALYSIS; SIGNAL NOISE RATIO;

CHEMISTRY TECHNIQUES, ANALYTICAL; FLUORESCENT DYES; HUMANS; HYDROGEN SULFIDE;

EID: 84880282899     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/09298673113209990005     Document Type: Article

References (69)

1. Brannan, R.G., Reactive Sulfur Species Act as Prooxidants in Liposomal and Skeletal Muscle Model Systems. J. Agric. Food Chem., 2010, 58, 3767-3771.
2. Gruhlke, M.C.H.; Slusarenko, A.J., The biology of reactive sulfur species (RSS). Plant Physiol. Biochem., 2012, 59, 98-107.
3. Jacob, C.; Anwar, A., The chemistry behind redox regulation with a focus on sulphur redox systems. Physiol. Plant., 2008, 133, 469-480.
4. Peng, H.; Cheng, Y.; Dai, C.; King, A.L.; Predmore, B.L.; Lefer, D.J.; Wang, B., A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood. Angew. Chem. Int. Ed. Engl., 2011, 50, 9672-9675.
5. Kimura, H., Hydrogen sulfide as a neuromodulator. Mol. Neuro biol., 2002, 26, 13-19.
6. Reiffenstein, R.; Hulbert, W.C.; Roth, S.H., Toxicology of hydrogen sulfide. Annu. Rev. Pharmacol. Toxicol., 1992, 32, 109-134.
7. Geng, B.; Chang, L.; Pan, C.; Qi, Y.; Zhao, J.; Pang, Y.; Du, J.; Tang, C., Endogenous hydrogen sulfide regulation of myocardial injury induced by isoproterenol. Biochem. Biophys. Res. Commun., 2004, 318, 756-763.
8. Zhao, W.; Zhang, J.; Lu, Y.; Wang, R., The vasorelaxant effect of H2S as a novel endogenous gaseous KATP channel opener. The EMBO journal, 2001, 20, 6008-6016.
9. Burnett, W.; King, E.; Grace, M.; Hall, W., Hydrogen sulfide poisoning: Review of 5 years' experience. Can. Med. Assoc. J., 1977, 117, 1277-1280.
10. Tang, C.; Li, X.; Du, J., Hydrogen sulfide as a new endogenous gaseous transmitter in the cardiovascular system. Current vascular pharmacology, 2006, 4, 17-22.
11. Lefer, D.J., A new gaseous signaling molecule emerges: Cardioprotective role of hydrogen sulfide. Science's STKE, 2007, 104, 17907-17908.
12. Hoidal, C.R.; Hall, A.H.; Robinson, M.D.; Kulig, K.; Rumack, B.H., Hydrogen sulfide poisoning from toxic inhalations of roofing asphalt fumes. Ann. Emergency Med., 1986, 15, 826-830.
13. Snyder, J.W.; Safir, E.F.; Summerville, G.P.; Middleberg, R.A., Occupational fatality and persistent neurological sequelae after mass exposure to hydrogen sulfide. The American journal of emergency medicine, 1995, 13, 199-203.
14. Wang, R., Two's company, three'sa crowd: Can H2S be the third endogenous gaseous transmitter? the FASEB Journal, 2002, 16, 1792-1798.
15. 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, 40-51.
16. Wagner, F.; Asfar, P.; Calzia, E.; Radermacher, P.; Szabó, C., Bench-to-bedside review: Hydrogen sulfide-the third gaseous transmitter: Applications for critical care. Crit Care, 2009, 13, 213-221.
17. Wang, R., The gasotransmitter role of hydrogen sulfide. Antioxid. Redox Signal., 2003, 5, 493-501.
18. Knight, L.D.; Presnell, S.E., Death by sewer gas: Case report of a double fatality and review of the literature. The American journal of forensic medicine and pathology, 2005, 26, 181-185.
19. Wasch, H.H.; Estrin, W.J.; Yip, P.; Bowler, R.; Cone, J.E., Prolongation of the P-300 latency associated with hydrogen sulfide exposure. Arch. Neurol., 1989, 46, 902-904.
20. Gabbay, D.S.; De Roos, F.; Perrone, J., Twenty-foot fall averts fatality from massive hydrogen sulfide exposure. The Journal of emergency medicine, 2001, 20, 141-144.
21. 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. Spectrochim. Acta. A. Mol. Biomol. Spectrosc., 2012, 90, 35-39.
22. Yu, F.; Li, P.; Song, P.; Wang, B.; Zhao, J.; Han, K., An ICT-based strategy to a colorimetric and ratiometric fluorescence probe for hydrogen sulfide in living cells. Chem Commun (Camb), 2012, 48, 2852-2854.
23. Montoya, L.A.; Pluth, M.D., Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells. Chem Commun (Camb), 2012, 48, 4767-4769.
24. Liu, C.; Peng, B.; Li, S.; Park, C.M.; Whorton, A.R.; Xian, M., Reaction based fluorescent probes for hydrogen sulfide. Org Lett, 2012, 14, 2184-2187.
25. Kartha, R.V.; Zhou, J.; Hovde, L.B.; Cheung, B.W.; Schroder, H., Enhanced detection of hydrogen sulfide generated in cell culture using an agar trap method. Anal. Biochem., 2012, 423, 102-108.
26. Chen, S.; Chen, Z.J.; Ren, W.; Ai, H.W., Reaction-Based Genetically Encoded Fluorescent Hydrogen Sulfide Sensors. J. Am. Chem. Soc., 2012, 134, 9589-9592.
27. Culotta, E.; Koshland Jr, D.E., NO news is good news. Science, 1992, 258, 1862-1865.
28. Nathan, C., Nitric oxide as a secretory product of mammalian cells. The FASEB journal: Official publication of the Federation of American Societies for Experimental Biology, 1992, 6, 3051-3064.
29. Ignarro, L.J.; Cirino, G.; Casini, A.; Napoli, C., Nitric oxide as a signaling molecule in the vascular system: An overview. J. Cardiovasc. Pharmacol., 1999, 34, 879-886.
30. Neill, S.J.; Desikan, R.; Clarke, A.; Hurst, R.D.; Hancock, J.T., Hydrogen peroxide and nitric oxide as signalling molecules in plants. J. Exp. Bot., 2002, 53, 1237-1247.
31. Ignarro, L.J., Nitric oxide: A unique endogenous signaling molecule in vascular biology (Nobel lecture). Angew. Chem. Int. Ed., 1999, 38, 1882-1892.
32. Anggård, E., Nitric oxide: Mediator, murderer, and medicine. Lancet, 1994, 343, 1199-1206.
33. Shaul, P.W.; Smart, E.J.; Robinson, L.J.; German, Z.; Yuhanna, I.S.; Ying, Y.; Anderson, R.G.W.; Michel, T., Acylation targets endothelial nitric-oxide synthase to plasmalemmal caveolae. J. Biol. Chem., 1996, 271, 6518-6522.
34. Morita, T.; Perrella, M.A.; Lee, M.E.; Kourembanas, S., Smooth muscle cell-derived carbon monoxide is a regulator of vascular cGMP. Proc. Natl. Acad. Sci. U. S. A., 1995, 92, 1475-1479.
35. Ryter, S.W.; Otterbein, L.E.; Morse, D.; Choi, A.M.K., Heme oxygenase/carbon monoxide signaling pathways: Regulation and functional significance. Mol. Cell. Biochem., 2002, 234, 249-263.
36. Clark, J.E.; Naughton, P.; Shurey, S.; Green, C.J.; Johnson, T.R.; Mann, B.E.; Foresti, R.; Motterlini, R., Cardioprotective actions by a water-soluble carbon monoxide-releasing molecule. Circul. Res., 2003, 93, e2-e8.
37. Bilban, M.; Haschemi, A.; Wegiel, B.; Chin, B.Y.; Wagner, O.; Otterbein, L.E., Heme oxygenase and carbon monoxide initiate homeostatic signaling. J. Mol. Med., 2008, 86, 267-279.
38. Amersi, F.; Shen, X.D.; Anselmo, D.; Melinek, J.; Iyer, S.; Southard, D.J.; Katori, M.; Volk, H.D.; Busuttil, R.W.; Buelow, R., Ex vivo exposure to carbon monoxide prevents hepatic ischemia/reperfusion injury through p38 MAP kinase pathway. Hepatology, 2002, 35, 815-823.
39. Piantadosi, C.A., Carbon monoxide, reactive oxygen signaling, and oxidative stress. Free Radical Biol. Med., 2008, 45, 562-569.
40. Miller, T.W.; Isenberg, J.S.; Roberts, D.D., Molecular regulation of tumor angiogenesis and perfusion via redox signaling. Chem. Rev., 2009, 109, 3099-3124.
41. Dominy, J.E.; Stipanuk, M.H., New roles for cysteine and transsulfuration enzymes: Production of H2S, a neuromodulator and smooth muscle relaxant. Nutr. Rev., 2004, 62, 348-353.
42. Kimura, H., Hydrogen sulfide: From brain to gut. Antioxidants & redox signaling, 2010, 12, 1111-1123.
43. Searcy, D.G.; Lee, S.H., Sulfur reduction by human erythrocytes. J. Exp. Zool., 1998, 282, 310-322.
44. Whiteman, M.; Moore, P.K., Hydrogen sulfide and the vasculature: A novel vasculoprotective entity and regulator of nitric oxide bioavailability? J. Cell. Mol. Med., 2009, 13, 488-507.
45. Predmore, B.L.; Lefer, D.J.; Gojon, G., Hydrogen sulfide in biochemistry and medicine. Antioxid Redox Signal, 2012, 17, 119-140.
46. Baskar, R.; Bian, J., Hydrogen sulfide gas has cell growth regulatory role. Eur. J. Pharmacol., 2011, 656, 5-9.
47. Lefer, D.J., A new gaseous signaling molecule emerges: Cardioprotective role of hydrogen sulfide. PNAS, 2007, 104, 17907-17908.
48. Szabó, G.; Veres, G.; Radovits, T.; Gero, D.; Módis, K.; Miesel-Gröschel, C.; Horkay, F.; Karck, M.; Szabó, C., Cardioprotective effects of hydrogen sulfide. Nitric Oxide, 2011, 25, 201-210.
49. Predmore, B.L.; Lefer, D.J., Development of hydrogen sulfidebased therapeutics for cardiovascular disease. J Cardiovasc Transl Res, 2010, 3, 487-498.
50. Papapetropoulos, A.; Pyriochou, A.; Altaany, Z.; Yang, G.; Marazioti, A.; Zhou, Z.; Jeschke, M.G.; Branski, L.K.; Herndon, D.N.; Wang, R., Hydrogen sulfide is an endogenous stimulator of angiogenesis. Proceedings of the National Academy of Sciences, 2009, 106, 21972-21977.
51. Wang, M.J.; Cai, W.J.; Li, N.; Ding, Y.J.; Chen, Y.; Zhu, Y.C., The hydrogen sulfide donor NaHS promotes angiogenesis in a rat model of hind limb ischemia. Antioxid Redox Signal, 2010, 12, 1065-1077.
52. Szabó, C.; Papapetropoulos, A., Hydrogen sulphide and angiogenesis: Mechanisms and applications. Br. J. Pharmacol., 2011, 164, 853-865.
53. Jha, S.; Calvert, J.W.; Duranski, M.R.; Ramachandran, A.; Lefer, D.J., Hydrogen sulfide attenuates hepatic ischemia-reperfusion injury: Role of antioxidant and antiapoptotic signaling. American Journal of Physiology-Heart and Circulatory Physiology, 2008, 295, H801-H806.
54. Wang, R., Hydrogen sulfide: The third gasotransmitter in biology and medicine. Antioxidants & redox signaling, 2010, 12, 1061-1064.
55. Fiorucci, S.; Antonelli, E.; Distrutti, E.; Rizzo, G.; Mencarelli, A.; Orlandi, S.; Zanardo, R.; Renga, B.; Di Sante, M.; Morelli, A., Inhibition of hydrogen sulfide generation contributes to gastric injury caused by anti-inflammatory nonsteroidal drugs. Gastro enterology, 2005, 129, 1210-1224.
56. Chunyu, Z.; Junbao, D.; Dingfang, B.; Hui, Y.; Xiuying, T.; Chaoshu, T., The regulatory effect of hydrogen sulfide on hypoxic pulmonary hypertension in rats. Biochem. Biophys. Res. Commun., 2003, 302, 810-816.
57. Fiorucci, S.; Antonelli, E.; Mencarelli, A.; Orlandi, S.; Renga, B.; Rizzo, G.; Distrutti, E.; Shah, V.; Morelli, A., The third gas: H2S regulates perfusion pressure in both the isolated and perfused normal rat liver and in cirrhosis. Hepatology, 2005, 42, 539-548.
58. Eto, K.; Asada, T.; Arima, K.; Makifuchi, T.; Kimura, H., Brain hydrogen sulfide is severely decreased in Alzheimer's disease. Biochem. Biophys. Res. Commun., 2002, 293, 1485-1488.
59. Xuan, W.; Sheng, C.; Cao, Y.; He, W.; Wang, W., Fluorescent probes for the detection of hydrogen sulfide in biological systems. Angew. Chem. Int. Ed. Engl., 2012, 51, 2282-2284.
60. Sun, W.; Wu, J.; Li, J.; Fang, H.; Du, L.; Li, M., Boronate Can Be the Fluorogenic Switch for the Detection of Hydrogen Peroxide. Curr. Med. Chem., 2012, 19, 3622-3634.
61. Sasakura, K.; Hanaoka, K.; Shibuya, N.; Mikami, Y.; Kimura, Y.; Komatsu, T.; Ueno, T.; Terai, T.; Kimura, H.; Nagano, T., Development of a highly selective fluorescence probe for hydrogen sulfide. J. Am. Chem. Soc., 2011, 133, 18003-18005.
62. Qian, Y.; Karpus, J.; Kabil, O.; Zhang, S.Y.; Zhu, H.L.; Banerjee, R.; Zhao, J.; He, C., Selective fluorescent probes for live-cell monitoring of sulphide. Nature communications, 2011, 2, 495.
63. Liu, C.; 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. Engl., 2011, 50, 10327-10329.
64. 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, 10078-10080.
65. 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 lipopolysaccharideinduced inflammation in the mouse. the FASEB Journal, 2005, 19, 1196-1198.
66. Cody, J.; Mandal, S.; Yang, L.; Fahrni, C.J., Differential tuning of the electron transfer parameters in 1, 3, 5-triarylpyrazolines: A rational design approach for optimizing the contrast ratio of fluorescent probes. J. Am. Chem. Soc., 2008, 130, 13023-13032.
67. Loudet, A.; Burgess, K., BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties. Chem. Rev., 2007, 107, 4891-4932.
68. Galardon, E.; Tomas, A.; Roussel, P.; Artaud, I., New fluorescent zinc complexes: Towards specific sensors for hydrogen sulfide in solution. Dalton Trans, 2009, 9126-9130.
69. Zhang, R.; Sun, Y.; Tsai, H.; Tang, C.; Jin, H.; Du, J., Hydrogen Sulfide Inhibits L-Type Calcium Currents Depending upon the Protein Sulfhydryl State in Rat Cardiomyocytes. PLoS One, 2012, 7, e37073.