Polysulfides link H2S to protein thiol oxidation

Antioxidants and Redox Signaling

Volumn 19, Issue 15, 2013, Pages 1749-1765

  Greiner, Romy ^a   Pálinkás, Zoltán ^b   Bäsell, Katrin ^c   Becher, Dörte ^c   Antelmann, Haike ^c   Nagy, Péter ^b   Dick, Tobias P ^a  

^a GERMAN CANCER RESEARCH CENTER   (Germany)

^b NATIONAL INSTITUTE OF ONCOLOGY   (Hungary)

^c UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; FERROUS CHLORIDE; GLUTATHIONE; HYDROGEN SULFIDE; PHOSPHATIDYLINOSITOL 3,4,5 TRISPHOSPHATE 3 PHOSPHATASE; SODIUM SULFIDE; THIOCYANATE POTASSIUM; THIOL; GYY 4137; MORPHOLINE DERIVATIVE; PHOSPHOROTHIOIC ACID DERIVATIVE; POLYSULFIDE; PROTEIN; SODIUM BISULFIDE; SULFIDE; THIOL DERIVATIVE;

ALKALINITY; ALKYLATION; ARTICLE; CONTROLLED STUDY; DISULFIDE BOND; EMBRYO; HUMAN; HUMAN CELL; OXIDATION; OXIDATION REDUCTION STATE; PRIORITY JOURNAL; TAUTOMERIZATION; ULTRAVIOLET SPECTROSCOPY; CELL LINE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYME ACTIVATION; ENZYME ACTIVE SITE; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION; SOLUTION AND SOLUBILITY;

CATALYTIC DOMAIN; CELL LINE; CYSTEINE; ENZYME ACTIVATION; HUMANS; HYDROGEN SULFIDE; KINETICS; MORPHOLINES; ORGANOTHIOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; PROTEINS; PTEN PHOSPHOHYDROLASE; SOLUTIONS; SULFHYDRYL COMPOUNDS; SULFIDES;

EID: 84886255283     PISSN: 15230864     EISSN: 15577716     Source Type: Journal    
DOI: 10.1089/ars.2012.5041     Document Type: Article

References (47)

1. Cai WJ, Wang MJ, Moore P.K., Jin HM, Yao T, and Zhu YC. The novel proangiogenic effect of hydrogen sulfide is dependent on Akt phosphorylation. Cardiovasc Res 76: 29-40, 2007. (Pubitemid 47362041)
2. Chen KY and Morris JC. Kinetics of oxidation of aqueous sulfide by O2. Environ Sci Technol 6: 529, 1972.
3. Chi BK, Gronau K, Mader U., Hessling B, Becher D, and Antelmann H. S-bacillithiolation protects against hypochlorite stress in Bacillus subtilis as revealed by transcriptomics and redox proteomics. Mol Cell Proteomics 10: M111.009506, 2011.
4. Coletta C, Papapetropoulos A, Erdelyi K., Olah G, Modis K, Panopoulos P., Asimakopoulou A, Gero D, Sharina I., Martin E, and Szabo C. 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: 9161-9166, 2012.
5. Collman JP, Ghosh S, Dey A., and Decreau RA. Using a functional enzyme model to understand the chemistry behind hydrogen sulfide induced hibernation. Proc Natl Acad Sci U S A 106: 22090-22095, 2009.
6. Debiemme-Chouvy C., Wartelle C, and Sauvage FX. First evidence of the oxidation and regeneration of polysulfides at a GaAs electrode, under anodic conditions. A study by in situ UV-visible spectroelectrochemistry. J Phys Chem B 108: 18291-18296, 2004.
7. Denu JM and Dixon JE. Protein tyrosine phosphatases: mechanisms of catalysis and regulation. Curr Opin Chem Biol 2: 633-641, 1998. (Pubitemid 128645721)
8. Gutscher M, Pauleau AL, Marty L, Brach T., Wabnitz GH, Samstag Y, Meyer AJ, and Dick TP. Real-time imaging of the intracellular glutathione redox potential. Nat Methods 5: 553-559, 2008. (Pubitemid 351761764)
9. Han J, Yen S, Han G., and Han P. Quantitation of hydrogen peroxide using tris(2-carboxyethyl)phosphine. Anal Biochem 234: 107-109, 1996. (Pubitemid 126335218)
10. Hanson GT, Aggeler R, Oglesbee D., Cannon M, Capaldi RA, Tsien R.Y., and Remington SJ. Investigating mitochondrial redox potential with redox-sensitive green fluorescent protein indicators. J Biol Chem 279: 13044-13053, 2004. (Pubitemid 38445882)
11. Hourihan JM, Kenna JG, and Hayes JD. The gasotransmitter hydrogen sulfide induces Nrf2-target genes by inactivating the Keap1 ubiquitin ligase substrate adaptor through formation of a disulfide bond between Cys-226 and Cys-613. Antioxid Redox Signal 19: 465-481, 2013.
12. Hu Y, Chen X, Pan T.T., Neo KL, Lee SW, Khin ES, Moore P.K., and Bian JS. Cardioprotection induced by hydrogen sulfide preconditioning involves activation of ERK and PI3K/Akt pathways. Pflugers Arch 455: 607-616, 2008. (Pubitemid 350160475)
13. Hughes MN, Centelles MN, and Moore KP. 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: 1346-1353, 2009.
14. Hylin JW and Wood JL. Enzymatic formation of polysulfides from mercaptopyruvate. J Biol Chem 234: 2141-2144, 1959.
15. Ishigami M, Hiraki K, Umemura K., Ogasawara Y, Ishii K, and Kimura H. A source of hydrogen sulfide and a mechanism of its release in the brain. Antioxid Redox Signal 11: 205-214, 2009.
16. Kabil O and Banerjee R. Redox biochemistry of hydrogen sulfide. J Biol Chem 285: 21903-21907, 2010.
17. Kamyshny A, Goifman A, Gun J., Rizkov D, and Lev O. Equilibrium distribution of polysulfide ions in aqueous solutions at 25 degrees C: a new approach for the study of polysulfides equilibria. Environ Sci Technol 38: 6633-6644, 2004. (Pubitemid 39658100)
18. Kimura H. Hydrogen sulfide: its production, release and functions. Amino Acids 41: 113-121, 2011.
19. Kimura Y, Mikami Y, Osumi K., Tsugane M, Oka JI, and Kimura H. Polysulfides are possible H2S-derived signaling molecules in rat brain. FASEB J 27: 2451-2457, 2013.
20. Krishnan N, Fu C, Pappin D.J., and Tonks NK. H2S-Induced sulfhydration of the phosphatase PTP1B and its role in the endoplasmic reticulum stress response. Sci Signal 4: ra86, 2011.
21. Kwon J, Lee SR, Yang K.S., Ahn Y., Kim YJ, Stadtman ER, and Rhee SG. Reversible oxidation and inactivation of the tumor suppressor PTEN in cells stimulated with peptide growth factors. Proc Natl Acad Sci U S A 101: 16419-16424, 2004. (Pubitemid 39557728)
22. Lee SR, Yang KS, Kwon J, Lee C., Jeong W, and Rhee SG. Reversible inactivation of the tumor suppressor PTEN by H2O2. J Biol Chem 277: 20336-20342, 2002. (Pubitemid 34967328)
23. Leslie NR, Bennett D, Lindsay Y.E., Stewart H., Gray A, and Downes CP. Redox regulation of PI 3-kinase signalling via inactivation of PTEN. EMBO J 22: 5501-5510, 2003. (Pubitemid 37279959)
24. Li L, Whiteman M, Guan Y.Y., Neo KL, Cheng Y, Lee SW, Zhao Y, Baskar R., Tan CH, and Moore PK. Characterization of a novel, water-soluble hydrogen sulfide-releasing molecule (GYY4137): new insights into the biology of hydrogen sulfide. Circulation 117: 2351-2360, 2008. (Pubitemid 351653553)
25. Meyer AJ and Dick TP. Fluorescent protein-based redox probes. Antioxid Redox Signal 13: 621-650, 2010.
26. Mikami Y, Shibuya N, Kimura Y., Nagahara N, Ogasawara Y, and Kimura H. Thioredoxin and dihydrolipoic acid are required for 3-mercaptopyruvate sulfurtransferase to produce hydrogen sulfide. Biochem J 439: 479-485, 2011.
27. Mueller EG. Trafficking in persulfides: delivering sulfur in biosynthetic pathways. Nat Chem Biol 2: 185-194, 2006.
28. Mustafa AK, Gadalla MM, Sen N, Kim S., Mu W, Gazi SK, Barrow R.K., Yang G., Wang R, and Snyder SH. H2S signals through protein S-sulfhydration. Sci Signal 2: ra72, 2009.
29. Mustafa AK, Sikka G, Gazi S.K., Steppan J., Jung SM, Bhunia AK, Barodka VM, Gazi F.K., Barrow RK, Wang R, Amzel LM, Berkowitz D.E., and Snyder SH. Hydrogen sulfide as endothelium-derived hyperpolarizing factor sulfhydrates potassium channels. Circ Res 109: 1259-1268, 2011.
30. Nagahara N, Nirasawa T, Yoshii T., and Niimura Y. Is novel signal transducer sulfur oxide involved in the redox cycle of persulfide at the catalytic site cysteine in a stable reaction intermediate of mercaptopyruvate sulfurtransferase? Antioxid Redox Signal 16: 747-753, 2012.
31. Nagy P and Winterbourn CC. Rapid reaction of hydrogen sulfide with the neutrophil oxidant hypochlorous acid to generate polysulfides. Chem Res Toxicol 23: 1541-1543, 2010.
32. Olson KR. A practical look at the chemistry and biology of hydrogen sulfide. Antioxid Redox Signal 17: 32-44, 2012.
33. Papapetropoulos A, Pyriochou A, Altaany Z., Yang G, Marazioti A, Zhou Z., Jeschke MG, Branski LK, Herndon DN, Wang R, and Szabo C. Hydrogen sulfide is an endogenous stimulator of angiogenesis. Proc Natl Acad Sci U S A 106: 21972-21977, 2009.
34. Paul BD and Snyder SH. H(2)S signalling through protein sulfhydration and beyond. Nat Rev Mol Cell Biol 13: 499-507, 2012.
35. Predmore BL, Lefer DJ, and Gojon G. Hydrogen sulfide in biochemistry and medicine. Antioxid Redox Signal 17: 119-140, 2012.
36. Ramazzini B. De morbis artificum diatriba [diseases of workers]. 1713. Am J Public Health 91: 1380-1382, 2001.
37. Schneider CA, Rasband WS, and Eliceiri KW. NIH Image to ImageJ: 25 years of image analysis. Nat Methods 9: 671-675, 2012.
38. Sen N, Paul BD, Gadalla M.M., Mustafa AK, Sen T, Xu R, Kim S., and Snyder SH. Hydrogen sulfide-linked sulfhydration of NF-kappaB mediates its antiapoptotic actions. Mol Cell 45: 13-24, 2012.
39. Shen X, Pattillo CB, Pardue S, Bir S.C., Wang R., and Kevil CG. Measurement of plasma hydrogen sulfide in vivo and in vitro. Free Radic Biol Med 50: 1021-1031, 2011.
40. Shen X, Peter EA, Bir S, Wang R., and Kevil CG. Analytical measurement of discrete hydrogen sulfide pools in biological specimens. Free Radic Biol Med 52: 2276-2283, 2012.
41. Shibuya N, Tanaka M, Yoshida M., Ogasawara Y, Togawa T, Ishii K., and Kimura H. 3-Mercaptopyruvate sulfurtransferase produces hydrogen sulfide and bound sulfane sulfur in the brain. Antioxid Redox Signal 11: 703-714, 2009.
42. Toohey JI. Sulphane sulphur in biological systems: a possible regulatory role. Biochem J 264: 625-632, 1989. (Pubitemid 20023429)
43. Toohey JI. Sulfur signaling: is the agent sulfide or sulfane? Anal Biochem 413: 1-7, 2011.
44. Wang R. Physiological implications of hydrogen sulfide: a whiff exploration that blossomed. Physiol Rev 92: 791-896, 2012.
45. Wood JL. Sulfane sulfur. Methods Enzymol 143: 25-29, 1987.
46. Xiao Y, Yeong Chit Chia J, Gajewski JE, Sio Seng Lio D, Mulhern TD, Zhu HJ, Nandurkar H, and Cheng HC. PTEN catalysis of phospholipid dephosphorylation reaction follows a two-step mechanism in which the conserved aspartate-92 does not function as the general acid - mechanistic analysis of a familial Cowden disease-associated PTEN mutation. Cell Signal 19: 1434-1445, 2007. (Pubitemid 46818909)
47. Yang G, Zhao K, Ju Y., Mani S, Cao Q, Puukila S., Khaper N, Wu L, and Wang R. Hydrogen sulfide protects against cellular senescence via S-sulfhydration of Keap1 and activation of Nrf2. Antioxid Redox Signal 18: 1906-1919, 2013.