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Volumn 55, Issue , 2013, Pages 1-7

Potential biological chemistry of hydrogen sulfide (H2S) with the nitrogen oxides

Author keywords

Free radicals; Hydrogen sulfide; Nitric oxide; Nitroxyl; Redox chemistry; S nitrosothiol

Indexed keywords

AMMONIA; CALCIUM; FATTY ACID; GLUTATHIONE; HYDROGEN SULFIDE; LIPOPOLYSACCHARIDE; N HYDROXYSULFENAMIDE; NITRITE; NITROGEN OXIDE; NITROPRUSSIDE SODIUM; NITROUS ACID; NITROUS OXIDE; PEROXYNITRITE; S NITROSOTHIOL; SULFENAMIDE DERIVATIVE; THIONITROUSACID; UNCLASSIFIED DRUG;

EID: 84870683393     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2012.11.005     Document Type: Review
Times cited : (80)

References (74)
  • 1
    • 0025883342 scopus 로고
    • Nitric-oxide - Physiology, pathophysiology, and pharmacology
    • S. Moncada, R.M.J. Palmer, and E.A. Higgs Nitric-oxide - physiology, pathophysiology, and pharmacology Pharmacol. Rev. 43 1991 109 142
    • (1991) Pharmacol. Rev. , vol.43 , pp. 109-142
    • Moncada, S.1    Palmer, R.M.J.2    Higgs, E.A.3
  • 2
    • 67849135882 scopus 로고    scopus 로고
    • Actions and interactions of nitric oxide, carbon monoxide and hydrogen sulphide in the cardiovascular system and in inflammation - A tale of three gases!
    • L. Li, A. Hsu, and P.K. Moore Actions and interactions of nitric oxide, carbon monoxide and hydrogen sulphide in the cardiovascular system and in inflammation - a tale of three gases! Pharmacol. Ther 123 2009 386 400
    • (2009) Pharmacol. Ther , vol.123 , pp. 386-400
    • Li, L.1    Hsu, A.2    Moore, P.K.3
  • 3
    • 0028815563 scopus 로고
    • Nitric-oxide - A new paradigm for 2nd-messengers
    • J.F. Kerwin, J.R. Lancaster, and P.L. Feldman Nitric-oxide - a new paradigm for 2nd-messengers J. Med. Chem. 38 1995 4343 4362
    • (1995) J. Med. Chem. , vol.38 , pp. 4343-4362
    • Kerwin, J.F.1    Lancaster, J.R.2    Feldman, P.L.3
  • 5
    • 38849162730 scopus 로고    scopus 로고
    • The nitrate-nitrite-nitric oxide pathway in physiology and therapeutics
    • J.O. Lundberg, E. Weitzberg, and M.T. Gladwin The nitrate-nitrite-nitric oxide pathway in physiology and therapeutics Nat. Rev. Drug Discovery 7 2008 156 167
    • (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 156-167
    • Lundberg, J.O.1    Weitzberg, E.2    Gladwin, M.T.3
  • 6
    • 84859857546 scopus 로고    scopus 로고
    • Small molecule signaling agents: The integrated chemistry and biochemistry of nitrogen oxides, oxides of carbon, dioxygen, hydrogen sulfide, and their derived species
    • J.M. Fukuto, S.J. Carrington, D.J. Tantillo, J.G. Harrison, L.J. Ignarro, B.A. Freeman, A. Chen, and D.A. Wink 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
    • (2012) Chem. Res. Toxicol. , vol.25 , pp. 769-793
    • Fukuto, J.M.1    Carrington, S.J.2    Tantillo, D.J.3    Harrison, J.G.4    Ignarro, L.J.5    Freeman, B.A.6    Chen, A.7    Wink, D.A.8
  • 7
    • 77749271091 scopus 로고    scopus 로고
    • Hydrogen sulfide as a gasotransmitter
    • M.M. Gadalla, and S.H. Snyder Hydrogen sulfide as a gasotransmitter J. Neurochem. 113 2010 14 26
    • (2010) J. Neurochem. , vol.113 , pp. 14-26
    • Gadalla, M.M.1    Snyder, S.H.2
  • 10
    • 79961076132 scopus 로고    scopus 로고
    • The therapeutic potential of hydrogen sulfide: Separating hype from hope
    • K.R. Olson The therapeutic potential of hydrogen sulfide: separating hype from hope Am. J. Physiol. Regul. Integr. Comp. Physiol 301 2011 R297 R312
    • (2011) Am. J. Physiol. Regul. Integr. Comp. Physiol , vol.301
    • Olson, K.R.1
  • 11
    • 84860758991 scopus 로고    scopus 로고
    • A practical look at the chemistry and biology of hydrogen sulfide
    • K.R. Olson A practical look at the chemistry and biology of hydrogen sulfide Antioxid. Redox Signaling 17 2012 32 44
    • (2012) Antioxid. Redox Signaling , vol.17 , pp. 32-44
    • Olson, K.R.1
  • 13
    • 77954579286 scopus 로고    scopus 로고
    • Redox biochemistry of hydrogen sulfide
    • O. Kabil, and R. Banerjee Redox biochemistry of hydrogen sulfide J. Biol. Chem. 285 2010 21903 21907
    • (2010) J. Biol. Chem. , vol.285 , pp. 21903-21907
    • Kabil, O.1    Banerjee, R.2
  • 14
    • 18744415136 scopus 로고    scopus 로고
    • The novel binding mode of N-alkyl-N′-hydroxyguanidine to neuronal nitric oxide synthase provides mechanistic insights into NO biosynthesis
    • H.Y. Li, H. Shimizu, M. Flinspach, J. Jamal, W.P. Yang, M. Xian, T.W. Cai, E.Z. Wen, Q.A. Jia, P.G. Wang, and T.L. Poulos The novel binding mode of N-alkyl-N′-hydroxyguanidine to neuronal nitric oxide synthase provides mechanistic insights into NO biosynthesis Biochemistry 41 2002 13868 13875
    • (2002) Biochemistry , vol.41 , pp. 13868-13875
    • Li, H.Y.1    Shimizu, H.2    Flinspach, M.3    Jamal, J.4    Yang, W.P.5    Xian, M.6    Cai, T.W.7    Wen, E.Z.8    Jia, Q.A.9    Wang, P.G.10    Poulos, T.L.11
  • 15
    • 84861850712 scopus 로고    scopus 로고
    • Shared signaling pathways among gasotransmitters
    • R. Wang Shared signaling pathways among gasotransmitters Proc. Natl. Acad. Sci. USA 109 2012 8801 8802
    • (2012) Proc. Natl. Acad. Sci. USA , vol.109 , pp. 8801-8802
    • Wang, R.1
  • 19
    • 79959901325 scopus 로고    scopus 로고
    • Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells
    • 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
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 10078-10080
    • Lippert, A.R.1    New, E.J.2    Chang, C.J.3
  • 20
    • 84859977825 scopus 로고    scopus 로고
    • Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells
    • 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
    • (2012) Chem. Commun. , vol.48 , pp. 4767-4769
    • Montoya, L.A.1    Pluth, M.D.2
  • 21
    • 0029780524 scopus 로고    scopus 로고
    • Mechanism of nitric oxide release from S-nitrosothiols
    • R.J. Singh, N. Hogg, J. Joseph, and B. Kalyanaraman Mechanism of nitric oxide release from S-nitrosothiols J. Biol. Chem. 271 1996 18596 18603
    • (1996) J. Biol. Chem. , vol.271 , pp. 18596-18603
    • Singh, R.J.1    Hogg, N.2    Joseph, J.3    Kalyanaraman, B.4
  • 22
    • 74049084627 scopus 로고    scopus 로고
    • Reaction between nitric oxide, glutathione, and oxygen in the presence and absence of protein: How are S-nitrosothiols formed?
    • A. Keszler, Y.H. Zhang, and N. Hogg Reaction between nitric oxide, glutathione, and oxygen in the presence and absence of protein: how are S-nitrosothiols formed? Free Radic. Biol. Med. 48 2010 55 64
    • (2010) Free Radic. Biol. Med. , vol.48 , pp. 55-64
    • Keszler, A.1    Zhang, Y.H.2    Hogg, N.3
  • 23
    • 0029160661 scopus 로고
    • Reaction of nitric-oxide with the free sulfhydryl-group of human serum-albumin yields a sulfenic acid and nitrous-oxide
    • E.G. Demaster, B.J. Quast, B. Redfern, and H.T. Nagasawa Reaction of nitric-oxide with the free sulfhydryl-group of human serum-albumin yields a sulfenic acid and nitrous-oxide Biochemistry 34 1995 11494 11499
    • (1995) Biochemistry , vol.34 , pp. 11494-11499
    • Demaster, E.G.1    Quast, B.J.2    Redfern, B.3    Nagasawa, H.T.4
  • 25
    • 1642588213 scopus 로고    scopus 로고
    • S-nitrosohemoglobin: A biochemical perspective
    • Y.H. Zhang, and N. Hogg S-nitrosohemoglobin: a biochemical perspective Free Radic. Biol. Med. 36 2004 947 958
    • (2004) Free Radic. Biol. Med. , vol.36 , pp. 947-958
    • Zhang, Y.H.1    Hogg, N.2
  • 28
    • 33645102456 scopus 로고    scopus 로고
    • Evidence for the formation of a novel nitrosothiol from the gaseous mediators nitric oxide and hydrogen sulphide
    • M. Whiteman, L. Li, I. Kostetski, S.H. Chu, J.L. Siau, M. Bhatia, and P.K. Moore 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
    • (2006) Biochem. Biophys. Res. Commun. , vol.343 , pp. 303-310
    • Whiteman, M.1    Li, L.2    Kostetski, I.3    Chu, S.H.4    Siau, J.L.5    Bhatia, M.6    Moore, P.K.7
  • 29
    • 78149314578 scopus 로고    scopus 로고
    • Hydrogen sulfide interacts with nitric oxide in the heart: Possible involvement of nitroxyl
    • Q.C. Yong, L.F. Hu, S.H. Wang, D.J. Huang, and J.S. Bian Hydrogen sulfide interacts with nitric oxide in the heart: possible involvement of nitroxyl Cardiovasc. Res. 88 2010 482 491
    • (2010) Cardiovasc. Res. , vol.88 , pp. 482-491
    • Yong, Q.C.1    Hu, L.F.2    Wang, S.H.3    Huang, D.J.4    Bian, J.S.5
  • 32
    • 0038643251 scopus 로고    scopus 로고
    • Nitroxyl gets to the heart of the matter
    • M. Feelisch Nitroxyl gets to the heart of the matter Proc. Natl. Acad. Sci. USA 100 2003 4978 4980
    • (2003) Proc. Natl. Acad. Sci. USA , vol.100 , pp. 4978-4980
    • Feelisch, M.1
  • 37
    • 0345306661 scopus 로고    scopus 로고
    • A tetrahydrobiopterin radical forms and then becomes reduced during N-omega-hydroxyarginine oxidation by nitric-oxide synthase
    • C.C. Wei, Z.Q. Wang, C. Hemann, R. Hille, and D.J. Stuehr A tetrahydrobiopterin radical forms and then becomes reduced during N-omega-hydroxyarginine oxidation by nitric-oxide synthase J. Biol. Chem. 278 2003 46668 46673
    • (2003) J. Biol. Chem. , vol.278 , pp. 46668-46673
    • Wei, C.C.1    Wang, Z.Q.2    Hemann, C.3    Hille, R.4    Stuehr, D.J.5
  • 38
    • 77953514816 scopus 로고    scopus 로고
    • Oxidative heme protein-mediated nitroxyl (HNO) generation
    • J.A. Reisz, E. Bechtold, and S.B. King Oxidative heme protein-mediated nitroxyl (HNO) generation Dalton Transact 39 2010 5203 5212
    • (2010) Dalton Transact , vol.39 , pp. 5203-5212
    • Reisz, J.A.1    Bechtold, E.2    King, S.B.3
  • 39
    • 0842310589 scopus 로고    scopus 로고
    • Xanthine oxidase converts nitric oxide to nitroxyl that inactivates the enzyme
    • M. Saleem, and H. Ohshima Xanthine oxidase converts nitric oxide to nitroxyl that inactivates the enzyme Biochem. Biophys. Res. Commun. 315 2004 455 462
    • (2004) Biochem. Biophys. Res. Commun. , vol.315 , pp. 455-462
    • Saleem, M.1    Ohshima, H.2
  • 41
    • 77952561979 scopus 로고    scopus 로고
    • Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex
    • J. Rosenthal, and S.J. Lippard Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex J. Am. Chem. Soc. 132 2010 5536
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 5536
    • Rosenthal, J.1    Lippard, S.J.2
  • 42
    • 79952578095 scopus 로고    scopus 로고
    • Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex
    • Y. Zhou, K. Liu, J.Y. Li, Y.A. Fang, T.C. Zhao, and C. Yao Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex Org. Lett. 13 2011 1290 1293
    • (2011) Org. Lett. , vol.13 , pp. 1290-1293
    • Zhou, Y.1    Liu, K.2    Li, J.Y.3    Fang, Y.A.4    Zhao, T.C.5    Yao, C.6
  • 43
    • 67649506367 scopus 로고    scopus 로고
    • Reductive phosphine-mediated ligation of nitroxyl (HNO)
    • J.A. Reisz, E.B. Klorig, M.W. Wright, and S.B. King Reductive phosphine-mediated ligation of nitroxyl (HNO) Org. Lett. 11 2009 2719 2721
    • (2009) Org. Lett. , vol.11 , pp. 2719-2721
    • Reisz, J.A.1    Klorig, E.B.2    Wright, M.W.3    King, S.B.4
  • 44
    • 79960853659 scopus 로고    scopus 로고
    • Rapid and selective nitroxyl (HNO) trapping by phosphines: Kinetics and new aqueous ligations for HNO detection and quantitation
    • J.A. Reisz, C.N. Zink, and S.B. King Rapid and selective nitroxyl (HNO) trapping by phosphines: kinetics and new aqueous ligations for HNO detection and quantitation J. Am. Chem. Soc. 133 2011 11675 11685
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 11675-11685
    • Reisz, J.A.1    Zink, C.N.2    King, S.B.3
  • 45
    • 37049077061 scopus 로고
    • Recent chemical studies of sodium-nitroprusside relevant to its hypotensive action
    • A.R. Butler, and C. Glidewell Recent chemical studies of sodium-nitroprusside relevant to its hypotensive action Chem. Soc. Rev. 16 1987 361 380
    • (1987) Chem. Soc. Rev. , vol.16 , pp. 361-380
    • Butler, A.R.1    Glidewell, C.2
  • 46
    • 0000524415 scopus 로고
    • The pentacyanonitrosylferrate ion. 5. The course of the reactions of nitroprusside with a range of thiols
    • A.R. Butler, A.M. Calsyharrison, C. Glidewell, and P.E. Sorensen The pentacyanonitrosylferrate ion. 5. The course of the reactions of nitroprusside with a range of thiols Polyhedron 7 1988 1197 1202
    • (1988) Polyhedron , vol.7 , pp. 1197-1202
    • Butler, A.R.1    Calsyharrison, A.M.2    Glidewell, C.3    Sorensen, P.E.4
  • 49
    • 0034286424 scopus 로고    scopus 로고
    • Reactivity of sulfur nucleophiles towards S-nitrosothiols
    • A.P. Munro, and D.L.H. Williams Reactivity of sulfur nucleophiles towards S-nitrosothiols J. Chem. Soc. Perkin Transact 2 2000 1794 1797
    • (2000) J. Chem. Soc. Perkin Transact , vol.2 , pp. 1794-1797
    • Munro, A.P.1    Williams, D.L.H.2
  • 52
    • 77958158351 scopus 로고    scopus 로고
    • Protein modifications involved in neurotransmitter and gasotransmitter signaling
    • N. Sen, and S.H. Snyder Protein modifications involved in neurotransmitter and gasotransmitter signaling Trends Neurosci. 33 2010 493 502
    • (2010) Trends Neurosci. , vol.33 , pp. 493-502
    • Sen, N.1    Snyder, S.H.2
  • 53
    • 79959340042 scopus 로고    scopus 로고
    • Protein sulfenic acid formation: From cellular damage to redox regulation
    • G. Roos, and J. Messens Protein sulfenic acid formation: from cellular damage to redox regulation Free Radic. Biol. Med. 51 2011 314 326
    • (2011) Free Radic. Biol. Med. , vol.51 , pp. 314-326
    • Roos, G.1    Messens, J.2
  • 54
    • 57549095616 scopus 로고    scopus 로고
    • Expanding the functional diversity of proteins through cysteine oxidation
    • K.G. Reddie, and K.S. Carroll Expanding the functional diversity of proteins through cysteine oxidation Curr. Opin. Chem. Biol. 12 2008 746 754
    • (2008) Curr. Opin. Chem. Biol. , vol.12 , pp. 746-754
    • Reddie, K.G.1    Carroll, K.S.2
  • 56
    • 0001666737 scopus 로고
    • Infrared-spectrum and force-field of matrix-isolated cis-thionylimide (HNSO)
    • P.O. Tchir, and R.D. Spratley Infrared-spectrum and force-field of matrix-isolated cis-thionylimide (HNSO) Can. J. Chem. 53 1975 2311 2317
    • (1975) Can. J. Chem. , vol.53 , pp. 2311-2317
    • Tchir, P.O.1    Spratley, R.D.2
  • 57
    • 0001160354 scopus 로고
    • Photolysis of matrix-isolated cis-thionylimide. 1. Identification and infrared-spectra of cis-HOSN, HSNO, and SNO
    • P.O. Tchir, and R.D. Spratley Photolysis of matrix-isolated cis-thionylimide. 1. Identification and infrared-spectra of cis-HOSN, HSNO, and SNO Can. J. Chem. 53 1975 2318 2330
    • (1975) Can. J. Chem. , vol.53 , pp. 2318-2330
    • Tchir, P.O.1    Spratley, R.D.2
  • 58
    • 0001666737 scopus 로고
    • Photolysis of matrix-isolated cis-thionylimide. 2. Identification and infrared-spectra of trans-HNSO and NSO
    • P.O. Tchir, and R.D. Spratley Photolysis of matrix-isolated cis-thionylimide. 2. Identification and infrared-spectra of trans-HNSO and NSO Can. J. Chem. 53 1975 2331 2336
    • (1975) Can. J. Chem. , vol.53 , pp. 2331-2336
    • Tchir, P.O.1    Spratley, R.D.2
  • 60
    • 39749189346 scopus 로고    scopus 로고
    • On the multireference character of S-nitrosothiols: A theoretical study of HSNO
    • Q.K. Timerghazin, A.M. English, and G.H. Peslherbe On the multireference character of S-nitrosothiols: a theoretical study of HSNO Chem. Phys. Lett. 454 2008 24 29
    • (2008) Chem. Phys. Lett. , vol.454 , pp. 24-29
    • Timerghazin, Q.K.1    English, A.M.2    Peslherbe, G.H.3
  • 64
    • 84862215205 scopus 로고    scopus 로고
    • Reaction-based genetically coded fluorescent hydrogen sulfide sensors
    • S. Chen, Z.J. Chen, W. Ren, and H.W. Ai Reaction-based genetically coded fluorescent hydrogen sulfide sensors J. Am. Chem. Soc. 134 2012 9589 9592
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 9589-9592
    • Chen, S.1    Chen, Z.J.2    Ren, W.3    Ai, H.W.4
  • 67
    • 80054072517 scopus 로고    scopus 로고
    • Formation and signaling actions of electrophilic lipids
    • F.J. Schopfer, C. Cipollina, and B.A. Freeman Formation and signaling actions of electrophilic lipids Chem. Rev. 111 2011 5997 6021
    • (2011) Chem. Rev. , vol.111 , pp. 5997-6021
    • Schopfer, F.J.1    Cipollina, C.2    Freeman, B.A.3
  • 71
    • 84858289256 scopus 로고    scopus 로고
    • NOSH-aspirin (NBS-1120), a novel nitric oxide- and hydrogen sulfide-releasing hybrid, is a potent inhibitor of colon cancer cell growth in vitro and in a xenograft mouse model
    • M. Chattopadhyay, R. Kodela, K.R. Olson, and K. Kashfi NOSH-aspirin (NBS-1120), a novel nitric oxide- and hydrogen sulfide-releasing hybrid, is a potent inhibitor of colon cancer cell growth in vitro and in a xenograft mouse model Biochem. Biophys. Res. Commun 419 2012 523 528
    • (2012) Biochem. Biophys. Res. Commun , vol.419 , pp. 523-528
    • Chattopadhyay, M.1    Kodela, R.2    Olson, K.R.3    Kashfi, K.4
  • 72
    • 84858182910 scopus 로고    scopus 로고
    • NOSH-aspirin: A novel nitric oxide-hydrogen sulfide-releasing hybrid: A new class of anti-inflammatory pharmaceuticals
    • R. Kodela, M. Chattopadhyay, and K. Kashfi NOSH-aspirin: a novel nitric oxide-hydrogen sulfide-releasing hybrid: a new class of anti-inflammatory pharmaceuticals ACS Med. Chem. Lett 3 2012 257 262
    • (2012) ACS Med. Chem. Lett , vol.3 , pp. 257-262
    • Kodela, R.1    Chattopadhyay, M.2    Kashfi, K.3
  • 74
    • 84863276285 scopus 로고    scopus 로고
    • Fluorescent probes for the detection of hydrogen sulfide in biological systems
    • 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
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2282-2284
    • Xuan, W.M.1    Sheng, C.Q.2    Cao, Y.T.3    He, W.H.4    Wang, W.5


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