Therapeutic applications of organosulfur compounds as novel hydrogen sulfide donors and/or mediators

Expert Review of Clinical Pharmacology

Volumn 4, Issue 1, 2011, Pages 123-133

  Gu, Xianfeng ^a   Zhu, Yi Zhun ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

hydrogen sulfide; hydrogen sulfide donor; hydrogen sulfide mediator

Indexed keywords

ACETYLSALICYLIC ACID; ALLIIN; ANTIHYPERTENSIVE AGENT; CYSTATHIONINE BETA SYNTHASE; CYSTEINE; CYSTEINE DERIVATIVE; DIALLYL DISULFIDE; DIALLYL TRISULFIDE; DICLOFENAC; ENZYME INHIBITOR; GLYCINE; GYY 4137; HYDROGEN SULFIDE; NONSTEROID ANTIINFLAMMATORY AGENT; ORGANOSULFUR DERIVATIVE; REAGENT; S ALLY CYSTEINE; S ASPIRIN; S DICLOFENAC; S PROPARGYL CYSTEINE; S PROPYL CYSTEINE; S SULINDAC; S VALPROATE; SULINDAC; UNCLASSIFIED DRUG; ZYZ 802;

ALZHEIMER DISEASE; ANTIHYPERTENSIVE ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; GARLIC; HEART PROTECTION; HUMAN; ISCHEMIC HEART DISEASE; NONHUMAN; REVIEW; VEGETABLE;

ALLIUM; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CYSTATHIONINE BETA-SYNTHASE; CYSTATHIONINE GAMMA-LYASE; CYSTEINE; HUMANS; HYDROGEN SULFIDE; INFLAMMATION; SULFUR COMPOUNDS;

EID: 78650438090     PISSN: 17512433     EISSN: None     Source Type: Journal    
DOI: 10.1586/ecp.10.129     Document Type: Review

References (77)

1. Abe K, Kimura H. The possible role ofhydrogen sulfide as an endogenous neuromodulator. J. Neurosci. 16(3), 1066-1071 (1996).
2. Lefer DJ. A new gaseous signaling molecule emerges: cardioprotective role of hydrogen sulfide. Proc. Natl Acad. Sci. USA 104(46), 17907-17908 (2007).
3. Wang X, Wang Q, Guo W, Zhu YZ. Hydrogen sulfide attenuates cardiac dysfunction in a rat model of heart failure: a mechanism through cardiac mitochondrial protection. Biosci. Rep. 31(2), 87-98 (2010).
4. 2S as a physiologic vasorelaxant: hypertension in mice with deletion of cystathionine g-lyase. Science 322(5901), 587-590 (2008).
5. Yang G, Wu L, Bryan S, Khaper N, Mani S, Wang R. Cystathionine g-lyase deficiency and overproliferation of smooth muscle cells. Cardiovasc. Res. 86(3), 487-495 (2010).
6. Kimura H, Nagai Y, Umemura K, Kimura Y. Physiological roles of hydrogen sulfide: synaptic modulation, neuroprotection, and smooth muscle relaxation. Antioxid. Redox Signal. 7(5-6), 795-803 (2005).
7. Lee M, Schwab C, Yu S, McGeer E, McGeer PL. Astrocytes produce the antiinflammatory and neuroprotective agent hydrogen sulfide. Neurobiol. Aging 30(10), 1523-1534 (2009).
8. Hu LF, Lu M, Tiong CX, Dawe GS, Hu G, Bian JS. Neuroprotective effects of hydrogen sulfide on Parkinson's disease rat models. Aging Cell 9(2), 135-146 (2010).
9. Medeiros JV, Bezerra VH, Gomes AS et al. Hydrogen sulfide prevents ethanol-induced gastric damage in mice: role of ATPsensitive potassium channels and capsaicinsensitive primary afferent neurons. J. Pharmacol. Exp. Ther. 330(3), 764-770 (2009).
10. 2S and suppressed insulin release in Zucker diabetic rats. Lab. Invest. 89(1), 59-67 (2009).
11. Sivarajah A, Collino M, Yasin M et al. Anti-apoptotic and anti-inflammatory effects of hydrogen sulfide in a rat model of regional myocardial I/R. Shock 31(3), 267-274 (2009).
12. Kery V, Bukovska G, Kraus JP. Transsulfuration depends on heme in addition to pyridoxal 5́-phosphate. Cystathionine b-synthase is a heme protein. J. Biol. Chem. 269(41), 25283-25288 (1994).
13. Erickson PF, Maxwell IH, Su LJ, Baumann M, Glode LM. Sequence of cDNA for rat cystathionine g-lyase and comparison of deduced amino acid sequence with related Escherichia coli enzymes. Biochem. J. 269(2), 335-340 (1990).
14. Meier M, Janosik M, Kery V, Kraus JP, Burkhard P. Structure of human cystathionine b-synthase: a unique pyridoxal 5́-phosphate-dependent heme protein. EMBO J. 20(15), 3910-3916 (2001).
15. Jhee KH, Kruger WD. The role of cystathionine b-synthase in homocysteine metabolism. Antioxid. Redox Signal. 7(5-6), 813-822 (2005).
16. 2S) - the third gas of interest for pharmacologists. Pharmacol. Rep. 59(1), 4-24 (2007).
17. Szabo C. Hydrogen sulphide and its therapeutic potential. Nat. Rev. Drug Discov. 6(11), 917-935 (2007).
18. Kimura H. Hydrogen sulfide: from brain to gut. Antioxid. Redox Signal. 12(9), 1111-1123 (2010).
19. 2S biogenesis via alternative trans-sulfuration reactions. J. Biol. Chem. 284(33), 22457-22466 (2009).
20. Chen CQ, Xin H, Zhu YZ. Hydrogen sulfide: third gaseous transmitter, but with great pharmacological potential. Acta Pharmacol. Sin. 28(11), 1709-1716 (2007).
21. 2S). Cell Biochem. Funct. 28(2), 95-106 (2010).
22. Olson KR, Whitfield NL. Hydrogen sulfide and oxygen sensing in the cardiovascular system. Antioxid. Redox Signal. 12(10), 1219-1234 (2010).
23. Elsey DJ, Fowkes RC, Baxter GF. l-cysteine stimulates hydrogen sulfide synthesis in myocardium associated with attenuation of ischemia-reperfusion injury. J. Cardiovasc. Pharmacol. Ther. 15(1), 53-59 (2010).
24. Fiorucci S. Prevention of nonsteroidal anti-inflammatory drug-induced ulcer: looking to the future. Gastroenterol. Clin. North Am. 38(2), 315-332 (2009).
25. Szabó C, Kiss L, Pankotai E. Cytoprotective and anti-inflammatory effects of hydrogen sulfide in macrophages and in mice. Crit. Care 11(Suppl. 2), P2 (2007).
26. Szabó C, Veres G, Radovits T, Karck M, Szabó G. Infusion of sodium sulfide improves myocardial and endothelial function in a canine model of cardiopulmonary bypass. Crit. Care 11(Suppl. 2), P1 (2007).
27. Li L, Bhatia M, Zhu YZ et al. Hydrogen sulfide is a novel mediator of lipopolysaccharide-induced inflammation in the mouse. FASEB J. 19(9), 1196-1198 (2005).
28. Zhang H, Zhi L, Moore PK, Bhatia M. Role of hydrogen sulfide in cecal ligation and puncture-induced sepsis in the mouse. Am. J. Physiol. Lung Cell. Mol. Physiol. 290(6), L1193-L1201 (2006).
29. Meng QH, Yang G, Yang W, Jiang B, Wu L, Wang R. Protective effect of hydrogen sulfide on balloon injury-induced neointima hyperplasia in rat carotid arteries. Am. J. Pathol. 170(4), 1406-1414 (2007).
30. Wallace JL. Hydrogen sulfide-releasing anti-inflammatory drugs. Trends Pharmacol. Sci. 28(10), 501-505 (2007).
31. Blachier F, Mariotti F, Huneau JF, Tome D. Effects of amino acid-derived luminal metabolites on the colonic epithelium and physiopathological consequences. Amino Acids 33(4), 547-562 (2007).
32. 2S-releasing enzymes of higher plants - from the field to the test tube and back. Plant Biol. (Stuttg.) 9(5), 582-588 (2007).
33. Kamoun P. Endogenous production of hydrogen sulfide in mammals. Amino Acids 26(3), 243-254 (2004).
34. Jacob C, Anwar A, Burkholz T. Perspective on recent developments on sulfurcontaining agents and hydrogen sulfide signaling. Planta Med. 74(13), 1580-1592 (2008).
35. Munchberg U, Anwar A, Mecklenburg S, Jacob C. Polysulfides as biologically active ingredients of garlic. Org. Biomol. Chem. 5, 1505-1518 (2007).
36. Powolny AA, Singh SV. Multitargeted prevention and therapy of cancer by diallyl trisulfide and related Allium vegetable-derived organosulfur compounds. Cancer Lett. 269(2), 305-314 (2008).
37. Milner JA. Mechanisms by which garlic and allyl sulfur compounds suppress carcinogen bioactivation. Garlic and carcinogenesis. Adv. Exp. Med. Biol. 492, 69-81 (2001).
38. Rahman K. Historical perspective on garlic and cardiovascular disease. J. Nutr. 131(3s), 977S-979S (2001).
39. 2S-mediated vasoactivity. Free Radic. Biol. Med. 41, S19-S20 (2006).
40. Benavides GA, Squadrito GL, Mills RW et al. Hydrogen sulfide mediates the vasoactivity of garlic. Proc. Natl Acad. Sci. USA 104(46), 17977-17982 (2007).
41. Chuah SC, Moore PK, Zhu YZ. S-allylcysteine mediates cardioprotection in an acute myocardial infarction rat model via a hydrogen sulfide-mediated pathway. Am. J. Physiol. Heart Circ. Physiol. 293(5), H2693-H2701 (2007).
42. Amagase H, Petesch BL, Matsuura H, Kasuga S, Itakura Y. Intake of garlic and its bioactive components. J. Nutr. 131(3s), 955S-962S (2001).
43. Amagase H. Clarifying the real bioactive constituents of garlic. J. Nutr. 136(3 Suppl.), 716S-725S (2006).
44. Truong D, Hindmarsh W, O'Brien PJ. The molecular mechanisms of diallyl disulfide and diallyl sulfide induced hepatocyte cytotoxicity. Chem. Biol. Interact. 180(1), 79-88 (2009).
45. Brosnan JT, Brosnan ME. The sulfurcontaining amino acids: an overview. J. Nutr. 136(6 Suppl.), 1636S-1640S (2006).
46. Haruyuki O, Daikichiro N, Hidehiko K, Hideaki Y. Synthesis of l-cysteine and its analogues by intact cells containing cysteine desulfhydrase. Agric. Biol. Chem. 45, 259-263 (1981).
47. Nishikawa-Ogawa M, Wanibuchi H, Morimura K et al. N-acetylcysteine and S-methylcysteine inhibit MeIQx rat hepatocarcinogenesis in the post-initiation stage. Carcinogenesis 27(5), 982-988 (2006).
48. Hsu CC, Huang CN, Hung YC, Yin MC. Five cysteine-containing compounds have antioxidative activity in Balb/cA mice. J. Nutr. 134(1), 149-152 (2004).
49. Atmaca G. Antioxidant effects of sulfur-containing amino acids. Yonsei Med. J. 45(5), 776-788 (2004).
50. Shirin H, Pinto JT, Kawabata Y et al. Antiproliferative effects of S-allylmercaptocysteine on colon cancer cells when tested alone or in combination with sulindac sulfide. Cancer Res. 61(2), 725-731 (2001).
51. Itokawa Y, Inoue K, Sasagawa S, Fujiwara M. Effect of S-methylcysteine sulfoxide, S-allylcysteine sulfoxide and related sulfur-containing amino acids on lipid metabolism of experimental hypercholesterolemic rats. J. Nutr. 103(1), 88-92 (1973).
52. Tcherniuk S, van Lis R, Kozielski F, Skoufias DA. Mutations in the human kinesin Eg5 that confer resistance to monastrol and S-trityl-l-cysteine in tumor derived cell lines. Biochem. Pharmacol. 79(6), 864-872 (2010).
53. Wang Q, Liu HR, Mu Q, Rose P, Zhu YZ. S-propargyl-cysteine protects both adult rat hearts and neonatal cardiomyocytes from ischemia/hypoxia injury: the contribution of the hydrogen sulfide-mediated pathway. J. Cardiovasc. Pharmacol. 54(2), 139-146 (2009).
54. 2S production. Antioxid. Redox Signal. 12(10), 1155-1165 (2010).
55. Gong QH, Pan LL, Liu XH, Wang Q, Huang H, Zhu YZ. S-propargyl-cysteine (ZYZ-802), a sulphur-containing amino acid, attenuates b-amyloid-induced cognitive deficits and pro-inflammatory response: involvement of ERK1/2 and NF-kB pathway in rats. Amino Acids DOI: 10.1007/s00726-010-0685-1 (2010) (Epub ahead of print).
56. Gong QH, Wang Q, Pan LL, Liu XH, Xin H, Zhu YZ. S-propargyl-cysteine, a novel hydrogen sulfide-modulated agent, attenuates lipopolysaccharide-induced spatial learning and memory impairment: involvement of TNF signaling and NF-kB pathway in rats. Brain Behav. Immun. 25(1), 110-119 (2010).
57. Gong QH, Wang Q, Pan LL, Liu XH, Huang H, Zhu YZ. Hydrogen sulfide attenuates lipopolysaccharide-induced cognitive impairment: A pro-inflammatory pathway in rats. Pharmacol. Biochem. Behav. 96(1), 52-58 (2010).
58. Johnston M, Jankowski D, Marcotte P et al. Suicide inactivation of bacterial cystathionine g-synthase and methionine g-lyase during processing of l-propargylglycine. Biochemistry 18(21), 4690-4701 (1979).
59. Tokoro M, Asai T, Kobayashi S, Takeuchi T, Nozaki T. Identification and characterization of two isoenzymes of methionine g-lyase from Entamoeba histolytica: a key enzyme of sulfur-amino acid degradation in an anaerobic parasitic protist that lacks forward and reverse trans-sulfuration pathways. J. Biol. Chem. 278(43), 42717-42727 (2003).
60. Kraus JP, Hasek J, Kozich V et al. Cystathionine g-lyase: clinical, metabolic, genetic, and structural studies. Mol. Genet. Metab. 97(4), 250-259 (2009).
61. Krupka HI, Huber R, Holt SC, Clausen T. Crystal structure of cystalysin from Treponema denticola: a pyridoxal 5́-phosphate-dependent protein acting as a haemolytic enzyme. EMBO J. 19(13), 3168-3178 (2000).
62. Steegborn C, Clausen T, Sondermann P et al. Kinetics and inhibition of recombinant human cystathionine g-lyase. Toward the rational control of transsulfuration. J. Biol. Chem. 274(18), 12675-12684 (1999).
63. Clausen T, Huber R, Messerschmidt A, Pohlenz HD, Laber B. Slow-binding inhibition of Escherichia coli cystathionine b-lyase by l- aminoethoxyvinylglycine: a kinetic and x-ray study. Biochemistry 36(41), 12633-12643 (1997).
64. Fiorucci S, Antonelli E. NO-NSAIDs: from inflammatory mediators to clinical readouts. Inflamm. Allergy Drug Targets 5(2), 121-131 (2006).
65. Li L, Rossoni G, Sparatore A, Lee LC, Del Soldato P, Moore PK. Anti-inflammatory and gastrointestinal effects of a novel diclofenac derivative. Free Radic. Biol. Med. 42(5), 706-719 (2007).
66. Sidhapuriwala J, Li L, Sparatore A, Bhatia M, Moore PK. Effect of S-diclofenac, a novel hydrogen sulfide releasing derivative, on carrageenaninduced hindpaw oedema formation in the rat. Eur. J. Pharmacol. 569(1-2), 149-154 (2007).
67. 2S- releasing derivative of diclofenac reduces inflammation in carrageenan-induced hindpaw oedema. Inflam. Res. 54(Suppl. 2), S185 (2005).
68. Baskar R, Sparatore A, Del Soldato P, Moore PK. Effect of S-diclofenac, a novel hydrogen sulfide releasing derivative inhibit rat vascular smooth muscle cell proliferation. Eur. J. Pharmacol. 594(1-3), 1-8 (2008).
69. Whiteman M, Li L, Rose P, Tan CH, Parkinson DB, Moore PK. The effect of hydrogen sulfide donors on lipopolysaccharide-induced formation of inflammatory mediators in macrophages. Antioxid. Redox Signal. 12(10), 1147-1154 (2010).
70. Rossoni G, Sparatore A, Tazzari V, Manfredi B, Del Soldato P, Berti F. The hydrogen sulphide-releasing derivative of diclofenac protects against ischaemiareperfusion injury in the isolated rabbit heart. Br. J. Pharmacol. 153(1), 100-109 (2008).
71. Bass SE, Sienkiewicz P, Macdonald CJ et al. Novel dithiolethione-modified nonsteroidal anti-inflammatory drugs inhuman hepatoma HepG2 and colon LS180 cells. Clin. Cancer Res. 15(6), 1964-1972 (2009).
72. Moody TW, Switzer C, Santana-Flores W et al. Dithiolethione modified valproate and diclofenac increase E-cadherin expression and decrease proliferation of non-small cell lung cancer cells. Lung Cancer 68(2), 154-160 (2010).
73. Lee M, Sparatore A, Del Soldato P, McGeer E, McGeer PL. Hydrogen sulfide-releasing NSAIDs attenuate neuroinflammation induced by microglial and astrocytic activation. Glia 58(1), 103-113 (2010).
74. Li L, Whiteman M, Guan YY et al. Characterization of a novel, water-soluble hydrogen sulfide-releasing molecule (GYY4137): new insights into the biology of hydrogen sulfide. Circulation 117(18), 2351-2360 (2008).
75. Li L, Salto-Tellez M, Tan CH, Whiteman M, Moore PK. GYY4137, a novel hydrogen sulfide-releasing molecule, protects against endotoxic shock in the rat. Free Radic. Biol. Med. 47(1), 103-113 (2009).
76. 2S-releasing drugs as pharmaceuticals. J. Med. Chem. 53(17), 6275-6286 (2010).
77. Wagner F, Asfar P, Calzia E, Radermacher P, Szabo C. Bench-to-bedside review: Hydrogen sulphide - the third gaseous transmitter: applications for critical care. Crit. Care 13(3), 213 (2009).