On the chemical biology of the nitrite/sulfide interaction

Nitric Oxide - Biology and Chemistry

Volumn 46, Issue , 2015, Pages 14-24

  Cortese Krott, Miriam M ^a   Fernandez, Bernadette O ^b   Kelm, Malte ^a   Butler, Anthony R ^c   Feelisch, Martin ^b  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Hypoxia; Nitrite; Nitroxyl; SSNO; Sulfane sulfur; Sulfide

Indexed keywords

NITRITE; PORPHYRIN; S NITROSOTHIOL; SULFIDE; SULFUR; XANTHINE OXIDASE; NITRIC OXIDE;

BIOCHEMISTRY; BLOOD PRESSURE; BLOOD VESSEL TONE; ENZYME ACTIVITY; HUMAN; MOLECULAR INTERACTION; NITROSATION; NONHUMAN; NUCLEOPHILICITY; PH; PRIORITY JOURNAL; REVIEW; ANIMAL; ANTIBODY SPECIFICITY; CHEMISTRY; METABOLISM;

ANIMALS; BIOCHEMISTRY; HUMANS; NITRIC OXIDE; NITRITES; ORGAN SPECIFICITY; SULFIDES;

EID: 84925499113     PISSN: 10898603     EISSN: 10898611     Source Type: Journal    
DOI: 10.1016/j.niox.2014.12.009     Document Type: Review

References (105)

1. L. Li, P. Rose, and P.K. Moore Hydrogen sulfide and cell signaling Ann. Rev. Pharm. Toxicol 51 2011 169 187 In: A.K. Cho, (Ed.)
2. C. Szabo Hydrogen sulphide and its therapeutic potential Nat. Rev. Drug Discov 6 2007 917 935
3. K.R. Olson The therapeutic potential of hydrogen sulfide: separating hype from hope Am. J. Physiol. Regul. Integr. Comp. Physiol 301 2011 R297 R312
4. G. Yang, L. Wu, B. Jiang, W. Yang, J. Qi, and K. Cao H2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine gamma-lyase Science 322 2008 587 590
5. R. Wang Two's company, three's a crowd: can H2S be the third endogenous gaseous transmitter? FASEB J. 16 2002 1792 1798
6. M. Feelisch, and K.R. Olson Embracing sulfide and CO to understand nitric oxide biology Nitric Oxide 35 2013 2 4
7. K. Ono, T. Akaike, T. Sawa, Y. Kumagai, D.A. Wink, and D.J. Tantillo Redox chemistry and chemical biology of HS-, hydropersulfides, and derived species: implications of their possible biological activity and utility Free Radic. Biol. Med 77 2014 82 94
8. J.W. Morse, F.J. Millero, J.C. Cornwell, and D. Rickard The chemistry of the hydrogen sulfide and iron sulfide systems in natural waters Earth Sci. Rev 24 2002 1 42
9. Q. Li, and J.R. Lancaster Jr. Chemical foundations of hydrogen sulfide biology Nitric Oxide 35 2013 21 34
10. K. Abe, and H. Kimura The possible role of hydrogen sulfide as an endogenous neuromodulator J. Neurosci 16 1996 1066 1071
11. M.Y. Ali, C.Y. Ping, Y.Y. Mok, L. Ling, M. Whiteman, and M. Bhatia Regulation of vascular nitric oxide in vitro and in vivo; a new role for endogenous hydrogen sulphide? Br. J. Pharmacol 149 2006 625 634
12. M. Kajimura, R. Fukuda, R.M. Bateman, T. Yamamoto, and M. Suematsu Interactions of multiple gas-transducing systems: hallmarks and uncertainties of CO, NO, and H2S gas biology Antioxid. Redox Signal 13 2010 157 192
13. P.J. Yoon, S.P. Parajuli, D.C. Zuo, P.K. Shahi, H.J. Oh, and H.R. Shin Interplay of hydrogen sulfide and nitric oxide on the pacemaker activity of interstitial cells of cajal from mouse small intestine Chonnam Med J 47 2011 72 79
14. K. Shatalin, E. Shatalina, A. Mironov, and E. Nudler H2S: a universal defense against antibiotics in bacteria Science 334 2011 986 990
15. M. Whiteman, L. Li, I. Kostetski, S.H. Chu, J.L. Siau, and M. Bhatia Evidence for the formation of a novel nitrosothiol from the gaseous mediators nitric oxide and hydrogen sulphide Biochem. Biophys. Res. Commun 343 2006 303 310
16. Q.C. Yong, J.L. Cheong, F. Hua, L.W. Deng, Y.M. Khoo, and H.S. Lee Regulation of heart function by endogenous gaseous mediators-crosstalk between nitric oxide and hydrogen sulfide Antioxid. Redox Signal 14 2011 2081 2091
17. C. Coletta, A. Papapetropoulos, K. Erdelyi, G. Olah, K. Modis, and P. Panopoulos Hydrogen sulfide and nitric oxide are mutually dependent in the regulation of angiogenesis and endothelium-dependent vasorelaxation Proc. Natl. Acad. Sci. U.S.A. 109 2012 9161 9166
18. M.R. Filipovic, J. Miljkovic, T. Nauser, M. Royzen, K. Klos, and T. Shubina Chemical characterization of the smallest S-nitrosothiol, HSNO; cellular cross-talk of H2S and S-nitrosothiols J. Am. Chem. Soc 134 2012 12016 12027
19. M.M. Cortese-Krott, B.O. Fernandez, J.L. Santos, E. Mergia, M. Grman, and P. Nagy Nitrosopersulfide (SSNO-) accounts for sustained NO bioactivity of S-nitrosothiols following reaction with sulfide Redox Biol 2 2014 234 244
20. J.O. Lundberg, M.T. Gladwin, A. Ahluwalia, N. Benjamin, N.S. Bryan, and A. Butler Nitrate and nitrite in biology, nutrition and therapeutics Nat. Chem. Biol 5 2009 865 869
21. N.S. Bryan, B.O. Fernandez, S.M. Bauer, M.F. Garcia-Saura, A.B. Milsom, and T. Rassaf Nitrite is a signaling molecule and regulator of gene expression in mammalian tissues Nat. Chem. Biol 1 2005 290 297
22. E.E. van Faassen, S. Bahrami, M. Feelisch, N. Hogg, M. Kelm, and D.B. Kim-Shapiro Nitrite as regulator of hypoxic signaling in mammalian physiology Med. Res. Rev 29 2009 683 741
23. E.A. Jansson, L. Huang, R. Malkey, M. Govoni, C. Nihlen, and A. Olsson A mammalian functional nitrate reductase that regulates nitrite and nitric oxide homeostasis Nat. Chem. Biol 4 2008 411 417
24. F. Bernheim, and M. Dixon The reduction of nitrates in animal tissues Biochem. J. 22 1928 125 134
25. A.R. Butler, and M. Feelisch Therapeutic uses of inorganic nitrite and nitrate: from the past to the future Circulation 117 2008 2151 2159
26. J.M. Fukuto, S.J. Carrington, D.J. Tantillo, J.G. Harrison, L.J. Ignarro, and B.A. Freeman Small molecule signaling agents: the integrated chemistry and biochemistry of nitrogen oxides, oxides of carbon, dioxygen, hydrogen sulfide, and their derived species Chem. Res. Toxicol 25 2012 769 793
27. G.K. Kolluru, X. Shen, and C.G. Kevil A tale of two gases: NO and H2S, foes or friends for life? Redox Biol 1 2013 313 318
28. B.S. King Potential biological chemistry of hydrogen sulfide (H2S) with the nitrogen oxides Free Radic. Biol. Med 55 2013 1 7
29. M.L. Lo Faro, B. Fox, J.L. Whatmore, P.G. Winyard, and M. Whiteman Hydrogen sulfide and nitric oxide interactions in inflammation Nitric Oxide 41 2014 38 47
30. J. Miljkovic, I. Kenkel, I. Ivanovic-Burmazovic, and M.R. Filipovic Generation of HNO and HSNO from nitrite by heme-iron-catalyzed metabolism with H2S Angew. Chem. Int. Ed Engl 52 2013 12061 12064
31. L. Grossi Hydrogen sulfide induces nitric oxide release from nitrite Bioorg. Med. Chem. Lett 19 2009 6092 6094
32. K.M. Kaster, A. Grigoriyan, G. Jenneman, and G. Voordouw Effect of nitrate and nitrite on sulfide production by two thermophilic, sulfate-reducing enrichments from an oil field in the North Sea Appl. Microbiol. Biotechnol 75 2007 195 203
33. H.H. Awad, and D.M. Stanbury Autoxidation of NO in aqueous solution Int. J. Chem. Kin 25 1993 375 381
34. S. Shiva, X. Wang, L.A. Ringwood, X. Xu, S. Yuditskaya, and V. Annavajjhala Ceruloplasmin is a NO oxidase and nitrite synthase that determines endocrine NO homeostasis Nat. Chem. Biol 2 2006 486 493
35. S. Moncada, R.M. Palmer, and E.A. Higgs Nitric oxide: physiology, pathophysiology, and pharmacology Pharmacol. Rev 43 1991 109 142
36. X. Liu, M.J. Miller, M.S. Joshi, D.D. Thomas, and J.R. Lancaster Accelerated reaction of nitric oxide with O2 within the hydrophobic interior of biological membranes Proc. Natl. Acad. Sci. U.S.A. 95 1998 2175 2179
37. M.N. Moller, Q. Li, D.A. Vitturi, J.M. Robinson, J.R. Lancaster Jr., and A. Denicola Membrane "lens" effect: focusing the formation of reactive nitrogen oxides from the∗NO/O2 reaction Chem. Res. Toxicol 20 2007 709 714
38. P. Wardman Fluorescent and luminescent probes for measurement of oxidative and nitrosative species in cells and tissues: progress, pitfalls, and prospects Free Radic. Biol. Med 43 2007 995 1022
39. G.Y. Markovits, S.E. Schwartz, and L. Newman Hydrolysis equilibrium of dinitrogen trioxide in dilute acid solution Inorg. Chem 20 1981 445 450
40. R.G. Pearson, H.R. Sobel, and J. Songstad Nucleophilic reactivity constants toward methyl iodide and trans-dichlorodi(pyridine)platinum(II) J. Am. Chem. Soc 90 1968 319 326
41. K.H. Becker, J. Kleffmann, R. Kurtenbach, and P. Wiesen Solubility of nitrous acid (HONO) in sulfuric acid solutions J. Phys. Chem 100 1996 14984 14990
42. C.D. Ritchie Nucleophilic reactivities toward cations Acc. Chem. Res 5 1972 348 354
43. J.I. Toohey Sulphane sulphur in biological systems: a possible regulatory role Biochem. J. 264 1989 625 632
44. J.I. Toohey Sulfur signaling: is the agent sulfide or sulfane? Anal. Biochem 413 2011 1 7
45. J.I. Toohey, and A.J. Cooper Thiosulfoxide (sulfane) sulfur: new chemistry and new regulatory roles in biology Molecules 19 2014 12789 12813
46. J. Zhu, K. Petit, A. Colson, S. DeBolt, and M. Sevilla Reactions of sulfhydryl and sulfide radicals with oxygen, hydrogen sulfide, hydrosulfide, and sulfide: formation of SO2•-, HSSH•-, HSS•2-and HSS• J. Phys. Chem 95 1991 3676 3681
47. G. Schwarzenbach, and A. Fischer Die Acidität der Sulfane und die Zusammensetzung wässeriger Polysulfidlösungen Helv. Chim. Acta 43 1960 1365 1390
48. A. Kamyshny Jr., J. Gun, D. Rizkov, T. Voitsekovski, and O. Lev Equilibrium distribution of polysulfide ions in aqueous solutions at different temperatures by rapid single phase derivatization Environ. Sci. Technol 41 2007 2395 2400
49. E. Divers, and T. Haga V. - Reduction of nitrites to hydroxylamine by hydrogen sulphide J. Chem. Soc. Trans 51 1887 48 51
50. L.S. Bagster CCCXLVI. - The reaction between nitrous acid and hydrogen sulphide J. Chem. Soc 1928 2631 2643
51. D.L.H. Williams Nitrosation reactions and the chemistry of nitric oxide 2004 Elsevier Amsterdam
52. M. Goehring, H.W. Kaloumenos, and J. Messner Zur Kenntnis der schwefligen Säure. II. Über Das Amid der Imidodisulfinsäure Z. Anorg. Allg. Chem 264 1951 48 53
53. M. Goehring, and J. Messner Zur Kenntnis der schwefligen Säure. III Das Sulfinimid und seine Isomeren Z. Anorg. Allg. Chem 268 1952 47 56
54. P.W. Schenk Über das Thionylimid SONH Ber. Dtsch. Chem. Ges 75 1942 94 99
55. R.P. Müller, M. Nonella, and J.R. Huber Spectroscopic investigation of HSNO in a low temperature matrix. UV, VIS, and IR-induced isomerisations Chem. Phys 87 1984 351 361
56. M. Nonella, R. Huber, and T.-K. Ha Photolytic preparation and isomerization of HNSO, HOSN, HSNO, and HONS in an Argon matrix. An experimental and theoretical study J. Phys. Chem 91 1987 5203 5209
57. C.-H. Lai, E.Y. Li, and P.-T. Chou Isomerization reactions of RSNO (R=H, C n H2 n+ 1 n ≤ 4) Theor. Chem. Acc 117 2007 145 152
58. F. Seel, R. Kuhn, G. Simon, M. Wagner, B. Krebs, and M. Dartmann PNP-Perthionitrit und PNP-Monothionitrit Z. Naturforsch. B 40 1985 1607 1617
59. F. Seel, and M. Wagner Reaction of sulfides with nitrogen monoxide in aqueous solution Z. Anorg. Allg. Chem 558 1988 189 192
60. S. Singh, J. Wishnok, M. Keshive, W. Deen, and S. Tannenbaum The chemistry of the S-nitrosoglutathione/glutathione system Proc. Natl. Acad. Sci. U.S.A. 93 1996 14428 14433
61. A.P. Dicks, E. Li, A.P. Munro, H.R. Swift, and D.L.H. Williams The reaction of S-nitrosothiols with thiols at high thiol concentration Can. J. Chem 76 1998 789 794
62. T. Komiyama, and K. Fujimori Kinetic studies of the reaction of S-nitroso-L-cysteine with L-cysteine Bioorg. Med. Chem. Lett 7 1997 175 180
63. K.R. Olson A practical look at the chemistry and biology of hydrogen sulfide Antioxid. Redox Signal 17 2012 32 44
64. R. Steudel Mechanism for the formation of elemental sulfur from aqueous sulfide in chemical and microbiological desulfurization processes Ind. Eng. Chem. Res 35 1996 1417 1423
65. A.R. Butler Formation of Meisenheimer-Jackson complexes in a non-polar solvent J. Chem. Soc. Perkin Trans 1 1975 1557 1558
66. M. Schmidt, and R. Wägerle Umsetzung von Schwefel mit Nitrit. Über Säuren des Schwefels, XIII Angew. Chem 70 1958 594 595
67. M. Schmidt, and R.R. Wägerle Über die Reaktion von elementarem Schwefel mit Natriumarsenit (im Vergleich mit Nitrit und Phosphit) Z. Anorg. Allg. Chem 330 1964 48 58
68. F. Seel, G. Simon, J. Schuh, M. Wagner, B. Wolf, and I. Ruppert Untersuchung der Umsetzung von Schwefel mit Natriumnitrit in DMF, DMSO und HMPT Z. Anorg. Allg. Chem 538 1986 177 190
69. F. Seel, and M. Wagner The reaction of polysulfides with nitrogen monoxide in non-acqueous solvents- nitrosodisulfides Z. Naturforsch 40 1985 762
70. S.P. Singh, J.S. Wishnok, M. Keshive, W.M. Deen, and S.R. Tannenbaum The chemistry of the S-nitrosoglutathione/glutathione system Proc. Natl. Acad. Sci. U.S.A. 93 1996 14428 14433
71. A.P. Munro, and D.L.H. Williams Reactivity of sulfur nucleophiles towards S-nitrosothiols J. Chem. Soc. Perkin Trans 2 2000 1794 1797
72. P. Nagy, Z. Palinkas, A. Nagy, B. Budai, I. Toth, and A. Vasas Chemical aspects of hydrogen sulfide measurements in physiological samples Biochim. Biophys. Acta 2014 1840 876 891
73. M. Feelisch, T. Rassaf, S. Mnaimneh, N. Singh, N.S. Bryan, and D. Jourd'Heuil Concomitant S-, N-, and heme-nitros(yl)ation in biological tissues and fluids: implications for the fate of NO in vivo FASEB J. 16 2002 1775 1785
74. J. Rodriguez, R.E. Maloney, T. Rassaf, N.S. Bryan, and M. Feelisch Chemical nature of nitric oxide storage forms in rat vascular tissue Proc. Natl. Acad. Sci. U.S.A. 100 2003 336 341
75. T. Rassaf, M. Preik, P. Kleinbongard, T. Lauer, C. Heiss, and B.E. Strauer Evidence for in vivo transport of bioactive nitric oxide in human plasma J. Clin. Invest 109 2002 1241 1248
76. T. Rassaf, M. Feelisch, and M. Kelm Circulating NO pool: assessment of nitrite and nitroso species in blood and tissues Free Radic. Biol. Med 36 2004 413 422
77. X. 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
78. N.S. Bryan, T. Rassaf, R.E. Maloney, C.M. Rodriguez, F. Saijo, and J.R. Rodriguez Cellular targets and mechanisms of nitros(yl)ation: an insight into their nature and kinetics in vivo Proc. Natl. Acad. Sci. U.S.A. 101 2004 4308 4313
79. 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
80. K. Cosby, K.S. Partovi, J.H. Crawford, R.P. Patel, C.D. Reiter, and S. Martyr Nitrite reduction to nitric oxide by deoxyhemoglobin vasodilates the human circulation Nat. Med 9 2003 1498 1505
81. E. Nagababu, S. Ramasamy, R. Albernethy, and M. Rifkind Active nitric oxide produced in the red cell under hypoxic conditions by deoxyhemoglobin-mediated nitrite reduction J. Biol. Chem 278 2003 46349 46356
82. M. Totzeck, U.B. Hendgen-Cotta, P. Luedike, M. Berenbrink, J.P. Klare, and H.J. Steinhoff Nitrite regulates hypoxic vasodilation via myoglobin-dependent nitric oxide generation Circulation 126 2012 325 334
83. A. Webb, A. Milsom, K. Rathod, W. Chu, S. Qureshi, and M. Lovell Mechanisms underlying erythrocyte and endothelial nitrite reduction to nitric oxide in hypoxia: role for xanthine oxidoreductase and endothelial nitric oxide synthase Circ. Res 103 2008 957 964
84. J.L. Zweier, P. Wang, A. Samouilov, and P. Kuppusamy Enzyme-independent formation of nitric oxide in biological tissues Nat. Med 1 1995 804 809
85. R. Aamand, T. Dalsgaard, F.B. Jensen, U. Simonsen, A. Roepstorff, and A. Fago Generation of nitric oxide from nitrite by carbonic anhydrase: a possible link between metabolic activity and vasodilation Am. J. Physiol. Heart Circ. Physiol 297 2009 H2068 H2074
86. R.P. Patel, N. Hogg, and D.B. Kim-Shapiro The potential role of the red blood cell in nitrite-dependent regulation of blood flow Cardiovasc. Res 89 2011 507 515
87. B.Y. Owusu, R. Stapley, and R.P. Patel Nitric oxide formation versus scavenging: the red blood cell balancing act J. Physiol 590 2012 4993 5000
88. A.R. Butler, and J.H. Ridd Formation of nitric oxide from nitrous acid in ischemic tissue and skin Nitric Oxide 10 2004 20 24
89. A.J. Elliot, D.R. McCracken, G.V. Buxton, and N.D. Wood Estimation of rate constants for near-diffusion-controlled reactions in water at high temperatures J. Chem. Soc. Faraday Trans 86 1990 1539 1547
90. S. Basu, R. Grubina, J. Huang, J. Conradie, Z. Huang, and A. Jeffers Catalytic generation of N2O3 by the concerted nitrite reductase and anhydrase activity of hemoglobin Nat. Chem. Biol 3 2007 785 794
91. J.S. Stamler, O. Jaraki, J. Osborne, D.I. Simon, J. Keaney, and J. Vita Nitric oxide circulates in mammalian plasma primarily as an S-nitroso adduct of serum albumin Proc. Natl. Acad. Sci. U.S.A. 89 1992 7674 7677
92. D.L.H. Williams The chemistry of S-nitrosothiols Acc. Chem. Res 32 1999 869 876
93. K.A. Broniowska, and N. Hogg The chemical biology of S-nitrosothiols Antioxid. Redox Signal 17 2012 969 980
94. L. Liu, A. Hausladen, M. Zeng, L. Que, J. Heitman, and J.S. Stamler A metabolic enzyme for S-nitrosothiol conserved from bacteria to humans Nature 410 2001 490 494
95. S. Oae, K. Shinhama, and Y.H. Kim Direct conversion of arylamines to the halides by deamination with thionitrite or related compounds and anhydrous copper (II) halides Bull. Chem. Soc. Jpn 53 1980 1065 1069
96. D.J. Barnett, J. McAninly, and D.L.H. Williams Transnitrosation between nitrosothiols and thiols J. Chem. Soc. Perkin Trans 2 1994 1131 1133
97. D.J. Barnett, A. Rios, and D.L.H. Williams NO-group transfer (transnitrosation) between S-nitrosothiols and thiols. Part 2 J. Chem. Soc. Perkin Trans 2 1995 1279 1282
98. M. Feelisch, B.O. Fernandez, N.S. Bryan, M.F. Garcia-Saura, S. Bauer, and D.R. Whitlock Tissue processing of nitrite in hypoxia an intricate interplay of nitric oxide-generating and-scavenging systems J. Biol. Chem 283 2008 33927 33934
99. K.R. Olson, and N.L. Whitfield Hydrogen sulfide and oxygen sensing in the cardiovascular system Antioxid. Redox Signal 12 2010 1219 1234
100. K.R. Olson Hydrogen sulfide as an oxygen sensor Clin. Chem. Lab. Med 51 2013 623 632
101. T. Mitsui, and T. Kondo Increased breath nitrous oxide after ingesting nitrate in patients with atrophic gastritis and partial gastrectomy Clin. Chim. Acta 345 2004 129 133
102. J.R. Hickok, S. Sahni, H. Shen, A. Arvind, C. Antoniou, and L.W. Fung Dinitrosyliron complexes are the most abundant nitric oxide-derived cellular adduct: biological parameters of assembly and disappearance Free Radic. Biol. Med 51 2011 1558 1566
103. A.F. Vanin Dinitrosyl iron complexes with thiolate ligands: physico-chemistry, biochemistry and physiology Nitric Oxide 21 2009 1 13
104. C.A. Bosworth, J.C. Toledo Jr., J.W. Zmijewski, Q. Li Jr., and J.R. Lancaster Dinitrosyliron complexes and the mechanism(s) of cellular protein nitrosothiol formation from nitric oxide Proc. Natl. Acad. Sci. U.S.A. 106 2009 4671 4676
105. M. Boese, P.I. Mordvintcev, A.F. Vanin, R. Busse, and A. Mulsch S-nitrosation of serum albumin by dinitrosyl-iron complex J. Biol. Chem 270 1995 29244 29249