Chemical aspects of hydrogen sulfide measurements in physiological samples

Biochimica et Biophysica Acta - General Subjects

Volumn 1840, Issue 2, 2014, Pages 876-891

  Nagy, Péter ^a   Pálinkás, Zoltán ^a   Nagy, Attila ^a   Budai, Barna ^a   Tóth, Imre ^b   Vasas, Anita ^a  

^a NATIONAL INSTITUTE OF ONCOLOGY   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Blood sulfide pool; Coordination chemistry; Hydrogen sulfide; Protonation equilibria; Redox chemistry; Tissue sulfide measurement

Indexed keywords

AZIDE; BROMOBIMANE; COPPER ION; DISULFIDE; FLUORESCENT DYE; HEMOPROTEIN; HYDROGEN SULFIDE; IRON; METHYLENE BLUE; NITRO DERIVATIVE; PERSULFIDE DERIVATIVE; POLYSULFIDE; SULFIDE; SULFUR; UNCLASSIFIED DRUG;

BIOLOGICAL ACTIVITY; BIOSYNTHESIS; BLOOD LEVEL; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; GAS CHROMATOGRAPHY; HUMAN; ION SELECTIVE ELECTRODE; MOLECULAR INTERACTION; MOLECULAR PROBE; NONHUMAN; NUCLEOPHILICITY; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON TRANSPORT; REVIEW; SYSTEMS BIOLOGY; THERMODYNAMICS; TISSUE LEVEL; CEREBROSPINAL FLUID; CHEMICAL ANALYSIS; CHRONIC OBSTRUCTIVE LUNG DISEASE; CONCENTRATION (PARAMETERS); FLUORESCENCE; GINGIVA; MASS SPECTROMETRY; PLASMA; SERUM; SHOCK; SYNOVIAL FLUID; TONGUE; UMBILICAL VEIN ENDOTHELIAL CELL; URINE;

3-MERCAPTOPYRUVATE SULFURTRANSFERASE; 3MST; 4-(2-HYDROXYETHYL)-1-PIPERAZINEETHANE-SULFONIC ACID; 5,5-DITHIOBIS-(2-NITROBENZOIC ACID); BLOOD SULFIDE POOL; CBS; CCO; COORDINATION CHEMISTRY; CSE; CYS; CYSTATHIONINE BETA-SYNTHASE; CYSTATHIONINE GAMMA-LYASE; CYTOCHROME C OXIDASE; D,L-DITHIOTREITOL; DIETHYLENETRIAMINE-PENTAACETIC-ACID; DTNB; DTPA; DTT; GAS CHROMATOGRAPHY; GC; GLUTATHIONE; GSH; HEPES; HSOH; HYDROGEN SULFIDE; L-CYSTEINE; MB; MBB; METHYLENE BLUE METHOD; MONOBROMOBIMANE METHOD; PBS; PERSULFIDE; PHOSPHATE BUFFERED SALINE; PROTONATION EQUILIBRIA; REACTIVE OXYGEN SPECIES; REDOX CHEMISTRY; ROS; RSOH; RSSH; SDB; SULFENIC ACID; SULFENIC ACID DERIVATIVE; SULFIDE DIBIMANE; TISSUE SULFIDE MEASUREMENT; TRIS; TRIS(HYDROXYMETHYL)AMINOMETHANE;

ANIMALS; CELL PHYSIOLOGICAL PHENOMENA; FLUORESCENT DYES; HUMANS; HYDROGEN SULFIDE;

EID: 84890121826     PISSN: 03044165     EISSN: 18728006     Source Type: Journal    
DOI: 10.1016/j.bbagen.2013.05.037     Document Type: Review

References (160)

1. M.H. Stipanuk, and P.W. Beck Characterization of the enzymic capacity for cysteine desulfhydration in liver and kidney of the rat Biochem. J. 206 1982 267 277
2. K. Abe, and H. Kimura The possible role of hydrogen sulfide as an endogenous neuromodulator J. Neurosci. 16 1996 1066 1071 (Pubitemid 26140863)
3. H. Kimura Hydrogen sulfide: from brain to gut Antioxid. Redox Signal. 12 2010 1111 1123
4. D.J. Lefer A new gaseous signaling molecule emerges: cardioprotective role of hydrogen sulfide Proc. Natl. Acad. Sci. U. S. A. 104 2007 17907 17908 (Pubitemid 350210795)
5. B.L. Predmore, D.J. Lefer, and G. Gojon Hydrogen sulfide in biochemistry and medicine Antioxid. Redox Signal. 17 2012 119 140
6. C. Szabo Hydrogen sulphide and its therapeutic potential Nat. Rev. Drug Discov. 6 2007 917 935 (Pubitemid 350042399)
7. M.S. Vandiver, and S.H. Snyder Hydrogen sulfide: a gasotransmitter of clinical relevance J. Mol. Med. 90 2012 255 263
8. R. Wang Physiological implications of hydrogen sulfide: a whiff exploration that blossomed Physiol. Rev. 92 2012 791 896
9. M. Whiteman, S. Le Trionnaire, M. Chopra, B. Fox, and J. Whatmore Emerging role of hydrogen sulfide in health and disease: critical appraisal of biomarkers and pharmacological tools Clin. Sci. 121 2011 459 488
10. 2S biogenesis Biochim. Biophys. Acta, Proteins Proteomics 1814 2011 1518 1527
11. N. Shibuya, M. Tanaka, M. Yoshida, Y. Ogasawara, T. Togawa, K. Ishii, and H. Kimura 3-Mercaptopyruvate sulfurtransferase produces hydrogen sulfide and bound sulfane sulfur in the brain Antioxid. Redox Signal. 11 2009 703 714
12. M. Goubern, M. Andriamihaja, T. Nubel, F. Blachier, and F. Bouillaud Sulfide, the first inorganic substrate for human cells FASEB J. 21 2007 1699 1706 (Pubitemid 46855615)
13. T.M. Hildebrandt, and M.K. Grieshaber Three enzymatic activities catalyze the oxidation of sulfide to thiosulfate in mammalian and invertebrate mitochondria FEBS J. 275 2008 3352 3361 (Pubitemid 351813547)
14. J.L. Wallace Physiological and pathophysiological roles of hydrogen sulfide in the gastrointestinal tract Antioxid. Redox Signal. 12 2010 1125 1133
15. R. Wang Hydrogen sulfide: a new EDRF Kidney Int. 76 2009 700 704
16. J.L. Wallace, J.G.P. Ferraz, and M.N. Muscara Hydrogen sulfide: an endogenous mediator of resolution of inflammation and injury Antioxid. Redox Signal. 17 2012 58 67
17. M. Whiteman, and P.G. Winyard Hydrogen sulfide and inflammation: the good, the bad, the ugly and the promising Expert. Rev. Clin. Pharmacol. 4 2011 13 32
18. L. Li, M. Bhatia, and P.K. Moore Hydrogen sulphide - a novel mediator of inflammation? Curr. Opin. Pharmacol. 6 2006 125 129 (Pubitemid 43362124)
19. 2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine gamma-lyase Science 322 2008 587 590
20. K.M. Desai, T. Chang, A. Untereiner, and L. Wu Hydrogen sulfide and the metabolic syndrome Expert. Rev. Clin. Pharmacol. 4 2011 63 73
21. 2S metabolism in mitochondria and its regulatory role in energy production Proc. Natl. Acad. Sci. U. S. A. 109 2012 2943 2948
22. 2S Chem. Res. Toxicol. 25 2012 1609 1615
23. H. Kimura, N. Shibuya, and Y. Kimura Hydrogen sulfide is a signaling molecule and a cytoprotectant Antioxid. Redox Signal. 17 2012 45 57
24. M.N. Hughes, M.N. Centelles, and K.P. Moore Making and working with hydrogen sulfide: The chemistry and generation of hydrogen sulfide in vitro and its measurement in vivo: a review Free Radic. Biol. Med. 47 2009 1346 1353
25. K.R. Olson A practical look at the chemistry and biology of hydrogen sulfide Antioxid. Redox Signal. 17 2012 32 44
26. X.G. Shen, C.B. Pattillo, S. Pardue, S.C. Bir, R. Wang, and C.G. Kevil Measurement of plasma hydrogen sulfide in vivo and in vitro Free Radic. Biol. Med. 50 2011 1021 1031
27. K.R. Olson Is hydrogen sulfide a circulating "gasotransmitter" in vertebrate blood? Biochim. Biophys. Acta, Bioenerg. 1787 2009 856 863
28. X.G. Shen, E.A. Peter, S. Bir, R. Wang, and C.G. Kevil Analytical measurement of discrete hydrogen sulfide pools in biological specimens Free Radic. Biol. Med. 52 2012 2276 2283
29. T. Ubuka Assay methods and biological roles of labile sulfur in animal tissues J. Chromatogr. B Anal. Technol. Biomed. Life Sci. 781 2002 227 249 (Pubitemid 35351670)
30. 2S-derived signaling molecules in rat brain FASEB J. 27 2013 2451 2457
31. 2S to Protein Thiol Oxidation 2013 10.1089/ars.2012.5041 (epub ahead of print)
32. A. Earn Shaw, and N.N. Greenwood Chemistry of the Elements 2nd ed. 1997 645 747
33. M. Nishida, T. Sawa, N. Kitajima, K. Ono, H. Inoue, H. Ihara, H. Motohashi, M. Yamamoto, M. Suematsu, H. Kurose, A. van der Vliet, B.A. Freeman, T. Shibata, K. Uchida, Y. Kumagai, and T. Akaike Hydrogen sulfide anion regulates redox signaling via electrophile sulfhydration Nat. Chem. Biol. 8 2012 714 724
34. 2S-donating sildenafil (ACS6) inhibits superoxide formation and gp91(phox) expression in arterial endothelial cells: role of protein kinases A and G Br. J. Pharmacol. 155 2008 984 994
35. E.R. DeLeon, G.F. Stoy, and K.R. Olson Passive loss of hydrogen sulfide in biological experiments Anal. Biochem. 421 2012 203 207
36. L. Li, M. Whiteman, Y.Y. Guan, K.L. Neo, Y. Cheng, S.W. Lee, Y. Zhao, R. Baskar, C.H. Tan, and P.K. Moore Characterization of a novel, water-soluble hydrogen sulfide-releasing molecule (GYY4137): new insights into the biology of hydrogen sulfide Circulation 117 2008 2351 2360 (Pubitemid 351653553)
37. D.D. Perrin Ionization Constants of Inorganic Acids and Bases in Aqueous Solution second edition 1982
38. J.C. Mathai, A. Missner, P. Kugler, S.M. Saparov, M.L. Zeidel, J.K. Lee, and P. Pohl No facilitator required for membrane transport of hydrogen sulfide Proc. Natl. Acad. Sci. U. S. A. 106 2009 16633 16638
39. 2 Environ. Sci. Technol. 6 1972 529 537
40. G.W. Luther III, A.J. Findlay, D.J. Macdonald, S.M. Owings, T.E. Hanson, R.A. Beinart, and P.R. Girguis Thermodynamics and kinetics of sulfide oxidation by oxygen: a look at inorganically controlled reactions and biologically mediated processes in the environment Front. Microbiol. 2 2011 62
41. 2S in seawater as a function of temperature, pH, and ionic-strength Environ. Sci. Technol. 21 1987 439 443
42. S. Carballal, M. Trujillo, E. Cuevasanta, S. Bartesaghi, M.N. Moller, L.K. Folkes, M.A. Garcia-Bereguiain, C. Gutierrez-Merino, P. Wardman, A. Denicola, R. Radi, and B. Alvarez Reactivity of hydrogen sulfide with peroxynitrite and other oxidants of biological interest Free Radic. Biol. Med. 50 2011 196 205
43. 2S: reaction with peroxynitrite and formation of a new nitric oxide donor, sulfinyl nitrite Biochem. J. 441 2012 609 621
44. D.W. Tapley, G.R. Buettner, and J.M. Shick Free radicals and chemiluminescence as products of the spontaneous oxidation of sulfide in seawater, and their biological implications Biol. Bull. 196 1999 52 56 (Pubitemid 29105399)
45. Z.F. Fu, X.M. Liu, B. Geng, L.P. Fang, and C.S. Tang Hydrogen sulfide protects rat lung from ischemia-reperfusion injury Life Sci. 82 2008 1196 1202
46. S. Jha, J.W. Calvert, M.R. Duranski, A. Ramachandran, and D.J. Lefer Hydrogen sulfide attenuates hepatic ischemia-reperfusion injury: role of antioxidant and antiapoptotic signaling Am. J. Physiol. Heart Circ. Physiol. 295 2008 H801 H806
47. Y. Kimura, and H. Kimura Hydrogen sulfide protects neurons from oxidative stress FASEB J. 18 2004 1165 1167 (Pubitemid 39561558)
48. M. Whiteman, N.S. Cheung, Y.Z. Zhu, S.H. Chu, J.L. Siau, B.S. Wong, J.S. Armstrong, and P.K. Moore Hydrogen sulphide: a novel inhibitor of hypochlorous acid-mediated oxidative damage in the brain? Biochem. Biophys. Res. Commun. 326 2005 794 798 (Pubitemid 39655989)
49. D. Yonezawa, F. Sekiguchi, M. Miyamoto, E. Taniguchi, M. Honjo, T. Masuko, H. Nishikawa, and A. Kawabata A protective role of hydrogen sulfide against oxidative stress in rat gastric mucosal epithelium Toxicology 241 2007 11 18 (Pubitemid 47599777)
50. H. Laggner, M.K. Muellner, S. Schreier, B. Sturm, M. Hermann, M. Exner, B.M.K. Gmeiner, and S. Kapiotis Hydrogen sulphide: a novel physiological inhibitor of LDL atherogenic modification by HOCl Free Radic. Res. 41 2007 741 747 (Pubitemid 46995255)
51. M. Whiteman, J.S. Armstrong, S.H. Chu, S. Jia-Ling, B.S. Wong, N.S. Cheung, B. Halliwell, and P.K. Moore The novel neuromodulator hydrogen sulfide: an endogenous peroxynitrite 'scavenger'? J. Neurochem. 90 2004 765 768 (Pubitemid 38989409)
52. P. Nagy, and C.C. Winterbourn Rapid reaction of hydrogen sulfide with the neutrophil oxidant hypochlorous acid to generate polysulfides Chem. Res. Toxicol. 23 2010 1541 1543
53. M.R. Hoffmann Kinetics and mechanism of oxidation of hydrogen-sulfide by hydrogen-peroxide in acidic solution Environ. Sci. Technol. 11 1977 61 66
54. G. Rabai, M. Orban, and I.R. Epstein Systematic design of chemical oscillators. 77. A model for the pH-regulated oscillatory reaction between hydrogen-peroxide and sulfide ion J. Phys. Chem. A 96 1992 5414 5419
55. 2S-induced sulfhydration of the phosphatase PTP1B and its role in the endoplasmic reticulum stress response Sci. Signal. 4 2011
56. 2S signals through protein S-sulfhydration Sci. Signal. 2 2009
57. A.K. Mustafa, G. Sikka, S.K. Gazi, J. Steppan, S.M. Jung, A.K. Bhunia, V.M. Barodka, F.K. Gazi, R.K. Barrow, R. Wang, L.M. Amzel, D.E. Berkowitz, and S.H. Snyder Hydrogen sulfide as endothelium-derived hyperpolarizing factor sulfhydrates potassium channels Circ. Res. 109 2011 1259 1268
58. 2S signalling through protein sulfhydration and beyond Nat. Rev. Mol. Cell Biol. 13 2012 499 507
59. N. Sen, B.D. Paul, M.M. Gadalla, A.K. Mustafa, T. Sen, R.S. Xu, S. Kim, and S.H. Snyder Hydrogen sulfide-linked sulfhydration of NF-kappa B mediates its antiapoptotic actions Mol. Cell 45 2012 13 24
60. O. Kabil, and R. Banerjee Redox biochemistry of hydrogen sulfide J. Biol. Chem. 285 2010 21903 21907
61. P. Nagy Kinetics and mechanisms of thiol-disulfide exchange covering direct substitution and thiol oxidation-mediated pathways Antioxid. Redox Signal. 18 2013 1623 1641
62. R.W. Nielsen, C. Tachibana, N.E. Hansen, and J.R. Winther Trisulfides in proteins Antioxid. Redox Signal. 15 2011 67 75
63. P. Nagy, and C.C. Winterbourn Redox chemistry of biological thiols Advances in Molecular Toxicology vol. 4 2010 183 222
64. 2SO: synthesis and IR spectroscopic detection of HSOH Chem. Eur. J. 12 2006 832 844 (Pubitemid 43099288)
65. G. Winnewisser, F. Lewen, S. Thorwirth, M. Behnke, J. Hahn, J. Gauss, and E. Herbst Gas-phase detection of HSOH: synthesis by flash vacuum pyrolysis of di-tert-butyl sulfoxide and rotational-torsional spectrum Chem. Eur. J. 9 2003 5501 5510
66. W. Giggenbach Optical spectra and equilibrium distribution of polysulfide ions in aqueous solution at 20 Inorg. Chem. 11 1972 1201 1207
67. H. Mitsuhashi, S. Yamashita, H. Ikeuchi, T. Kuroiwa, Y. Kaneko, K. Hiromura, K. Ueki, and Y. Nojima Oxidative stress-dependent conversion of hydrogen sulfide to sulfite by activated neutrophils Shock 24 2005 529 534
68. M. Durand, and P. Weinstein Thiosulfate in human urine following minor exposure to hydrogen sulfide: implications for forensic analysis of poisoning Forensic Toxicol. 25 2007 92 95
69. S. Kage, H. Ikeda, N. Ikeda, A. Tsujita, and K. Kudo Fatal hydrogen sulfide poisoning at a dye works Leg. Med. (Tokyo) 6 2004 182 186 (Pubitemid 38844690)
70. D.C. Dorman, F.J.M. Moulin, B.E. McManus, K.C. Mahle, R.A. James, and M.F. Struve Cytochrome oxidase inhibition induced by acute hydrogen sulfide inhalation: correlation with tissue sulfide concentrations in the rat brain, liver, lung, and nasal epithelium Toxicol. Sci. 65 2002 18 25 (Pubitemid 34092686)
71. X.F. Duan, E. Block, Z. Li, T. Connelly, J. Zhang, Z.M. Huang, X.B. Su, Y. Pan, L.F. Wu, Q.Y. Chi, S. Thomas, S.Z. Zhang, M.H. Ma, H. Matsunami, G.Q. Chen, and H.Y. Zhuang Crucial role of copper in detection of metal-coordinating odorants Proc. Natl. Acad. Sci. U. S. A. 109 2012 3492 3497
72. R. Pietri, E. Roman-Morales, and J. Lopez-Garriga Hydrogen sulfide and hemeproteins: knowledge and mysteries Antioxid. Redox Signal. 15 2011 393 404
73. 2S induces a suspended animation-like state in mice Science 308 2005 518 (Pubitemid 40570576)
74. J. Collman, S. Ghosh, A. Dey, and R.A. Decreau Using a functional enzyme model to understand the chemistry behind hydrogen sulfide induced hibernation Proc. Natl. Acad. Sci. U. S. A. 106 2009 22090 22095
75. J.A. Berzofsky, J. Peisach, and B.L. Horecker Sulfheme proteins. IV. The stoichiometry of sulfur incorporation and the isolation of sulfhemin, the prosthetic group of sulfmyoglobin J. Biol. Chem. 247 1972 3783 3791
76. M.J. Chatfield, and G.N. Lamar H-1 nuclear-magnetic-resonance study of the prosthetic group in sulfhemoglobin Arch. Biochem. Biophys. 295 1992 289 296
77. G.K. Kolluru, X. Shen, and C.G. Kevil Detection of hydrogen sulfide in biological samples: current and future Expert. Rev. Clin. Pharmacol. 4 2011 9 12
78. P.R. Haddad, and A.L. Heckenberg Trace determination of sulfide by reversed-phase ion-interaction chromatography using pre-column derivatization J. Chromatogr. 447 1988 415 420
79. 35S into the Fe-S cluster of aconitase J. Biol. Chem. 259 1984 3145 3151 (Pubitemid 14159439)
80. S.E. Mylon, and G. Benoit Subnanomolar detection of acid-labile sulfides by the classical methylene blue method coupled to HPLC Environ. Sci. Technol. 35 2001 4544 4548 (Pubitemid 33070066)
81. H. Sakurai, S. Lien, and A.S. Pietro Determination of acid-labile sulfide and zero-valence sulfur in sub-chloroplast particles in the presence of sodium dodecyl-sulfate Anal. Biochem. 119 1982 372 377
82. J.M. Small, and H. Hintelmann Methylene blue derivatization then LC-MS analysis for measurement of trace levels of sulfide in aquatic samples Anal. Bioanal. Chem. 387 2007 2881 2886 (Pubitemid 46479952)
83. J.K. Fogo, and M. Popowsky Spectrophotometric determination of hydrogen sulfide: methylene blue method Anal. Chem. 21 1949 732 734
84. E. Braswell Evidence for trimerization in aqueous solutions of methylene blue J. Phys. Chem. 72 1968 2477 2483
85. Z.M. Zhao, and E.R. Malinowski Window factor analysis of methylene blue in water J. Chemom. 13 1999 83 94
86. J. Cline Spectrophotometric determination of hydrogen sulfide in natural waters Limnol. Oceanogr. 1969 454 458
87. T. Togawa, M. Ogawa, M. Nawata, Y. Ogasawara, K. Kawanabe, and S. Tanabe High-performance liquid-chromatographic determination of bound sulfide and sulfite and thiosulfate at their low-levels in human serum by precolumn fluorescence derivatization with monobromobimane Chem. Pharm. Bull. 40 1992 3000 3004 (Pubitemid 23021868)
88. A. Bengtsson, J. Johnson, P. Hill, J. Mulligan, D. Leviten, M. Insko, E. Mebel, P. Vertz, E. VandenEkart, C. Szabo, T. Deckwerth, and E.A. Wintner Use of mono-bromo-bimane to derivatize sulfide in whole blood: comparison of blood sulfide levels during atmospheric hydrogen sulfide exposure and intravenous sulfide infusion FASEB J. 22 2008
89. E.A. Wintner, T.L. Deckwerth, W. Langston, A. Bengtsson, D. Leviten, P. Hill, M.A. Insko, R. Dumpit, E. VandenEkart, C.F. Toombs, and C. Szabo A monobromobimane-based assay to measure the pharmacokinetic profile of reactive sulphide species in blood Br. J. Pharmacol. 160 2010 941 957
90. T.J. Chang, A. Untereiner, J.H. Liu, and L.Y. Wu Interaction of methylglyoxal and hydrogen sulfide in rat vascular smooth muscle cells Antioxid. Redox Signal. 12 2010 1093 1100
91. A.K. Chaturvedi, D.R. Smith, and D.V. Canfield A fatality caused by accidental production of hydrogen sulfide Forensic Sci. Int. 123 2001 211 214 (Pubitemid 33122042)
92. Y.H. Chen, W.Z. Yao, B. Geng, Y.L. Ding, M. Lu, M.W. Zhao, and C.S. Tang Endogenous hydrogen sulfide in patients with COPD Chest 128 2005 3205 3211 (Pubitemid 41699831)
93. P. Jappinen, and R. Tenhunen Hydrogen-sulfide poisoning - blood sulfide concentration and changes in heme metabolism Br. J. Ind. Med. 47 1990 283 285 (Pubitemid 20150044)
94. S.U. Khan, G.F. Morris, and M. Hidiroglou Rapid estimation of sulfide in rumen and blood with a sulfide-specific ion electrode Microchem. J. 25 1980 388 395
95. H. Lindell, P. Jappinen, and H. Savolainen Determination of sulfide in blood with an ion-selective electrode by pre-concentration of trapped sulfide in sodium-hydroxide solution Analyst 113 1988 839 840
96. B.H. McAnalley, W.T. Lowry, R.D. Oliver, and J.C. Garriott Determination of inorganic sulfide and cyanide in blood using specific ion electrodes - application to the investigation of hydrogen-sulfide and cyanide poisoning J. Anal. Toxicol. 3 1979 111 114 (Pubitemid 9204631)
97. I. Toth, P. Solymosi, and Z. Szabo Application of a sulfide-selective electrode in the absence of a pH-buffer Talanta 35 1988 783 788
98. D.G. Searcy, and M.A. Peterson Hydrogen sulfide consumption measured at low steady state concentrations using a sulfidostat Anal. Biochem. 324 2004 269 275 (Pubitemid 38019017)
99. J.E. Doeller, T.S. Isbell, G. Benavides, J. Koenitzer, H. Patel, R.P. Patel, J.R. Lancaster, V.M. Darley-Usmar, and D.W. Kraus Polarographic measurement of hydrogen sulfide production and consumption by mammalian tissues Anal. Biochem. 341 2005 40 51 (Pubitemid 40615718)
100. 2S in aquatic environments Anal. Chem. 68 1996 4351 4357
101. K. Funazo, M. Tanaka, K. Morita, M. Kamino, T. Shono, and H.L. Wu Pentafluorobenzyl para-toluenesulfonate as a new derivatizing reagent for gas-chromatographic determination of anions J. Chromatogr. 346 1985 215 225
102. S. Kage, T. Nagata, K. Kimura, and K. Kudo Extractive alkylation and gas chromatographic analysis of sulfide J. Forensic Sci. 33 1988 217 222 (Pubitemid 18038244)
103. K. Kimura, M. Hasegawa, K. Matsubara, C. Maseda, M. Kagawa, S. Takahashi, and K. Tanabe A fatal disaster case-based on exposure to hydrogen-sulfide - an estimation of the hydrogen-sulfide concentration at the scene Forensic Sci. Int. 66 1994 111 116
104. U. Hannestad, S. Margheri, and B. Sorbo A sensitive gas-chromatographic method for determination of protein-associated sulfur Anal. Biochem. 178 1989 394 398 (Pubitemid 19125362)
105. T. Ubuka, T. Abe, R. Kajikawa, and K. Morino Determination of hydrogen sulfide and acid-labile sulfur in animal tissues by gas chromatography and ion chromatography J. Chromatogr. B 757 2001 31 37 (Pubitemid 32424455)
106. J. Furne, A. Saeed, and M.D. Levitt Whole tissue hydrogen sulfide concentrations are orders of magnitude lower than presently accepted values Am. J. Physiol. Regul. Integr. Comp. Physiol. 295 2008 R1479 R1485
107. V. Vitvitsky, O. Kabil, and R. Banerjee High turnover rates for hydrogen sulfide allow for rapid regulation of its tissue concentrations Antioxid. Redox Signal. 17 2012 22 31
108. 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
109. C. Liu, J. Pan, S. Li, Y. Zhao, L.Y. Wu, C.E. Berkman, A.R. Whorton, and M. Xian Capture and visualization of hydrogen sulfide by a fluorescent probe Angew. Chem. Int. Ed. 50 2011 10327 10329
110. H.J. Peng, Y.F. Cheng, C.F. Dai, A.L. King, B.L. Predmore, D.J. Lefer, and B.H. Wang A fluorescent probe for fast and quantitative detection of hydrogen sulfide in blood Angew. Chem. Int. Ed. 50 2011 9672 9675
111. Y. Qian, J. Karpus, O. Kabil, S.Y. Zhang, H.L. Zhu, R. Banerjee, J. Zhao, and C. He Selective fluorescent probes for live-cell monitoring of sulphide Nat. Commun. 2 2011
112. K. Sasakura, K. Hanaoka, N. Shibuya, Y. Mikami, Y. Kimura, T. Komatsu, T. Ueno, T. Terai, H. Kimura, and T. Nagano Development of a highly selective fluorescence probe for hydrogen sulfide J. Am. Chem. Soc. 133 2011 18003 18005
113. W.M. Xuan, C.Q. Sheng, Y.T. Cao, W.H. He, and W. Wang Fluorescent probes for the detection of hydrogen sulfide in biological systems Angew. Chem. Int. Ed. 51 2012 2282 2284
114. F. Kazemi, A.R. Kiasat, and S. Sayyahi Chemoselective reduction of azides with sodium sulfide hydrate under solvent free conditions Phosphorus Sulfur Silicon Relat. Elem. 179 2004 1813 1817 (Pubitemid 39481568)
115. L.J. Pang, D. Wang, J. Zhou, L.H. Zhang, and X.S. Ye Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations Org. Biomol. Chem. 7 2009 4252 4266
116. E.M. Sletten, and C.R. Bertozzi Bioorthogonal chemistry: fishing for selectivity in a sea of functionality Angew. Chem. Int. Ed. 48 2009 6974 6998
117. S.K. Das, C.S. Lim, S.Y. Yang, J.H. Han, and B.R. Cho A small molecule two-photon probe for hydrogen sulfide in live tissues Chem. Commun. 48 2012 8395 8397
118. B.F. Chen, W. Li, C. Lv, M.M. Zhao, H.W. Jin, H.F. Jin, J.B. Du, L.R. Zhang, and X.J. Tang Fluorescent probe for highly selective and sensitive detection of hydrogen sulfide in living cells and cardiac tissues Analyst 138 2013 946 951
119. B.F. Chen, C. Lv, and X.J. Tang Chemoselective reduction-based fluorescence probe for detection of hydrogen sulfide in living cells Anal. Bioanal. Chem. 404 2012 1919 1923
120. 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
121. Z.S. Wu, Z. Li, L. Yang, J.H. Han, and S.F. Han Fluorogenic detection of hydrogen sulfide via reductive unmasking of o-azidomethylbenzoyl-coumarin conjugate Chem. Commun. 48 2012 10120 10122
122. F.B.A. 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
123. 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
124. M.Y. Wu, K. Li, J.T. Hou, Z. Huang, and X.Q. Yu A selective colorimetric and ratiometric fluorescent probe for hydrogen sulfide Org. Biomol. Chem. 10 2012 8342 8347
125. Y. Qian, L. Zhang, S.T. Ding, X. Deng, C. He, X.E. Zheng, H.L. Zhu, and J. Zhao A fluorescent probe for rapid detection of hydrogen sulfide in blood plasma and brain tissues in mice Chem. Sci. 3 2012 2920 2923
126. Z. Xu, L. Xu, J. Zhou, Y.F. Xu, W.P. Zhu, and X.H. Qian A highly selective fluorescent probe for fast detection of hydrogen sulfide in aqueous solution and living cells Chem. Commun. 48 2012 10871 10873
127. 2 + complex of dipicolylamine appended fluorescein Chem. Commun. 2009 7390 7392
128. F.P. Hou, J. Cheng, P.X. Xi, F.J. Chen, L. Huang, G.Q. Xie, Y.J. Shi, H.Y. Liu, D.C. Bai, and Z.Z. Zeng Recognition of copper and hydrogen sulfide in vitro using a fluorescein derivative indicator Dalton Trans. 41 2012 5799 5804
129. F.P. Hou, L. Huang, P.X. Xi, J. Cheng, X.F. Zhao, G.Q. Xie, Y.J. Shi, F.J. Cheng, X.J. Yao, D.C. Bai, and Z.Z. Zeng A retrievable and highly selective fluorescent probe for monitoring sulfide and imaging in living cells Inorg. Chem. 51 2012 2454 2460
130. Y.C. Chen, C.C. Zhu, Z.H. Yang, J.J. Chen, Y.F. He, Y. Jiao, W.J. He, L. Qiu, J.J. Cen, and Z.J. Guo A ratiometric fluorescent probe for rapid detection of hydrogen sulfide in mitochondria Angew. Chem. Int. Ed. 52 2013 1688 1691
131. 4 clusters Proc. Natl. Acad. Sci. U. S. A. 72 1975 231 234
132. M. Ishigami, K. Hiraki, K. Umemura, Y. Ogasawara, K. Ishii, and H. Kimura A source of hydrogen sulfide and a mechanism of its release in the brain Antioxid. Redox Signal. 11 2009 205 214
133. 2S-poisoned animals Arch. Toxicol. 64 1990 650 655
134. P. Nagy, T.P. Lechte, A.B. Das, and C.C. Winterbourn Conjugation of glutathione to oxidized tyrosine residues in peptides and proteins J. Biol. Chem. 287 2012 26068 26076
135. R. Cecil, and J.R. McPhee The sulfur chemistry of proteins Adv. Protein Chem. 14 1959 255 389
136. J.P. Danehy The chemistry of organic sulphur compounds 2 1966
137. J.W. Donovan, and T.M. White Alkaline hydrolysis of the disulfide bonds of ovomucoid and of low molecular weight aliphatic and aromatic disulfides Biochemistry 10 1971 32 38
138. J.F. Schneider, and J. Westley Metabolic interrelations of sulfur in proteins, thiosulfate, and cystine J. Biol. Chem. 244 1969 5735 5744
139. P. Nagy, G.N.L. Jameson, and C.C. Winterbourn Kinetics and mechanisms of the reaction of hypothiocyanous acid with 5-thio-2-nitrobenzoic acid and reduced glutathione Chem. Res. Toxicol. 22 2009 1833 1840
140. P.W. Riddles, R.L. Blakeley, and B. Zerner Ellman's reagent: 5,5′-dithiobis(2-nitrobenzoic acid) - a reexamination Anal. Biochem. 94 1979 75 81 (Pubitemid 9170207)
141. P. Nagy, and M.T. Ashby Reactive sulfur species: kinetics and mechanisms of the oxidation of cysteine by hypohalous acid to give cysteine sulfenic acid J. Am. Chem. Soc. 129 2007 14082 14091 (Pubitemid 350106102)
142. P. Nagy, K. Lemma, and M.T. Ashby Reactive sulfur species: kinetics and mechanisms of the reaction of cysteine thiosulfinate ester with cysteine to give cysteine sulfenic acid J. Org. Chem. 72 2007 8838 8846 (Pubitemid 350071714)
143. E. Helmerhorst, and G.B. Stokes Generation of an acid-stable and protein-bound persulfide-like residue in alkali-treated or sulfhydryl-treated insulin by a mechanism consonant with the beta-elimination hypothesis of disulfide bond lysis Biochemistry 22 1983 69 75
144. Z.X. Wang, T. Rejtar, Z.S. Zhou, and B.L. Karger Desulfurization of cysteine-containing peptides resulting from sample preparation for protein characterization by mass spectrometry Rapid Commun. Mass Spectrom. 24 2010 267 275
145. D.B. Volkin, and A.M. Klibanov Thermal-destruction processes in proteins involving cystine residues J. Biol. Chem. 262 1987 2945 2950
146. 2S/sulfide concentration in vertebrate blood and its potential significance in ischemic preconditioning and vascular signaling Am. J. Physiol. Regul. Integr. Comp. Physiol. 294 2008 R1930 R1937
147. K.R. Olson, M.J. Healy, Z. Qin, N. Skovgaard, B. Vulesevic, D.W. Duff, N.L. Whitfield, G.D. Yang, R. Wang, and S.F. Perry Hydrogen sulfide as an oxygen sensor in trout gill chemoreceptors Am. J. Physiol. Regul. Integr. Comp. Physiol. 295 2008 R669 R680
148. A. Van de Louw, and P. Haouzi Ferric iron and cobalt (III) compounds to safely decrease hydrogen sulfide in the body? Antioxid. Redox Signal. 2013 10.1089/ars.2012.4513 (epub ahead of print)
149. M.A. Insko, T.L. Deckwerth, P. Hill, C.F. Toombs, and C. Szabo Detection of exhaled hydrogen sulphide gas in rats exposed to intravenous sodium sulphide Br. J. Pharmacol. 157 2009 944 951
150. C.F. Toombs, M.A. Insko, E.A. Wintner, T.L. Deckwerth, H. Usansky, K. Jamil, B. Goldstein, M. Cooreman, and C. Szabo Detection of exhaled hydrogen sulphide gas in healthy human volunteers during intravenous administration of sodium sulphide Br. J. Clin. Pharmacol. 69 2010 626 636
151. K.R. Olson, N.L. Whitfield, S.E. Bearden, J.S. Leger, E. Nilson, Y. Gao, and J.A. Madden Hypoxic pulmonary vasodilation: a paradigm shift with a hydrogen sulfide mechanism Am. J. Physiol. Regul. Integr. Comp. Physiol. 298 2010 R51 R60
152. 2S biogenesis by human cystathionine gamma-lyase leads to the novel sulfur metabolites lanthionine and homolanthionine and is responsive to the grade of hyperhomocysteinemia J. Biol. Chem. 284 2009 11601 11612
153. 2S biogenesis via alternative trans-sulfuration reactions J. Biol. Chem. 284 2009 22457 22466
154. E.R. DeLeon, G.F. Stoy, and K.R. Olson Passive loss of hydrogen sulfide in biological experiments Anal. Biochem. 421 2012 203 207
155. A.S. Nashef, D.T. Osuga, and R.E. Feeney Determination of Hydrogen-Sulfide with 5,5'-Dithiobis-(2-Nitrobenzoic Acid), N-Ethylmaleimide, and Parachloromercuribenzoate Anal. Biochem. 79 1977 394 405 (Pubitemid 8105108)
156. M.D. Levitt, M.S. Abdel-Rehim, and J. Furne Free and acid-labile hydrogen sulfide concentrations in mouse tissues: anomalously high free hydrogen sulfide in aortic tissue Antioxid. Redox Signal. 15 2011 373 378
157. S.E.V. Phillips Structure and refinement of oxymyoglobin at 1.6-A resolution J. Mol. Biol. 142 1980 531 554 (Pubitemid 11193948)
158. S.V. Evans, B.P. Sishta, A.G. Mauk, and G.D. Brayer 3-Dimensional structure of cyanomet-sulfmyoglobin-c Proc. Natl. Acad. Sci. U. S. A. 91 1994 4723 4726
159. A.H. Robbins, and C.D. Stout Structure of activated aconitase - formation of the 4Fe-4S cluster in the crystal Proc. Natl. Acad. Sci. U. S. A. 86 1989 3639 3643
160. T. Clausen, J.T. Kaiser, C. Steegborn, R. Huber, and D. Kessler Crystal structure of the cystine C-S lyase from Synechocystis: stabilization of cysteine persulfide for FeS cluster biosynthesis Proc. Natl. Acad. Sci. U. S. A. 97 2000 3856 3861 (Pubitemid 30226051)