Rocket fuel for the quantification of S-nitrosothiols. Highly specific reduction of S-nitrosothiols to thiols by methylhydrazine

References

• Ignarro LJ, Lipton H, Edwards JC, Baricos WH, Hyman HL, Kadowitz PJ, . Mechanism of vascular smooth-muscle relaxation by organic nitrates, nitrites, nitroprusside and nitric-oxide - Evidence for the involvement of S-nitrosothiols as active intermediates. J Pharmacol Exp Ther 1981;218: 739–749.
   PubMed Web of Science ®Google Scholar
• Moncada S, Higgs EA. Endogenous nitric oxide: physiology, pathology and clinical relevance. Eur J Clin Inves 1991;21: 361–374.
   PubMed Web of Science ®Google Scholar
• Knowles RG, Palacios M, Palmer RM, Moncada S. Formation of nitric oxide from L-arginine in the central nervous system: a transduction mechanism for stimulation of the soluble guanylate cyclase. Proc Natl Acad Sci USA 1989;86: 5159–5162.
   PubMed Web of Science ®Google Scholar
• Rees DD, Palmer RM, Moncada S. Role of endothelium- derived nitric oxide in the regulation of blood pressure. Proc Natl Acad Sci USA 1989;86:3375–3378.
   PubMed Web of Science ®Google Scholar
• MØller JKS, Skibsted LH. Mechanism of nitrosylmyoglobin autoxidation: temperature and oxygen pressure effects on the two consecutive reactions. Chem Eur J 2004;10: 2291–2300.
   Google Scholar
• Gow A, Luchsinger BP, Pawloski JR, Singel DJ, Stamler JS. The oxyhemoglobin reaction of nitric oxide. Proc Natl Acad Sci USA 1999;96:9027–9032.
   PubMed Web of Science ®Google Scholar
• Kowaluk EA, Fung HL. Spontaneous liberation of nitric oxide cannot account for invitro vascular relaxation by S. nitrosothiols. J Pharmacol Exp Ther 1990;255:1256–1264.
   PubMedGoogle Scholar
• Stamler JS, Simon DI, Osborne JA, Mullins ME, Jaraki O, Michel T, . S-Nitrosylation of proteins with nitric oxide: synthesis and characterization of biologically active compounds. Proc Natl Acad Sci USA 1992;89:444–448.
   PubMed Web of Science ®Google Scholar
• Stamler JS, Simon DI, Jaraki O, Osborne JA, Francis S, Mullins M, . S-nitrosylation of tissue-type plasminogen activator confers vasodilatory and antiplatelet properties on the enzyme. Proc Natl Acad Sci USA 1992; 89:8087–8091.
   PubMedGoogle Scholar
• Hess DT, Matsumoto A, Kim S, Marshall HE, Stamler JS. Protein S-nitrosylation: purview and parameters. Nat Rev Mol Cell Biol 2005;6:150–166.
   PubMed Web of Science ®Google Scholar
• Martinez-Ruiz A, Lamas S. S-nitrosylation: a potential new paradigm in signal transduction. Cardiovasc Res 2004; 62:43–52.
   PubMed Web of Science ®Google Scholar
• Stamler JS, Lamas S, Fang FC. Nitrosylation: The prototypic redox-based signaling mechanism. Cell 2001;106:675–683.
   PubMed Web of Science ®Google Scholar
• Forrester MT, Foster MW, Benhar M, Stamler JS. Detection of protein S-nitrosylation with the biotin-switch technique. Free Radic Biol Med 2009;46:119–126.
   PubMed Web of Science ®Google Scholar
• Gow A, Doctor A, Mannick J, Gaston B. S-nitrosothiol measurements in biological systems. J Chromatogr B 2007; 851:140–151.
   PubMed Web of Science ®Google Scholar
• Yang BK, Vivas EX, Reiter CD, Gladwin MT. Methodologies for the sensitive and specific measurement of S-nitrosothiols, iron-nitrosyls and nitrite in biological samples. Free Radic Res 2003;37:1–10.
   PubMed Web of Science ®Google Scholar
• Lopez-Sanchez LM, Muntane J, de la Mata M, Rodriguez-Ariza A. Unraveling the S-nitrosoproteome: tools and strategies. Proteomics 2009;9:808–818.
   Google Scholar
• Jaffrey SR, Erdjument-Bromage H, Ferris CD, Tempst P, Snyder SH. Protein S-nytrosylation: a physiological signal for neuronal nitric oxide. Nat Cell Biol 2001;3:193–197.
   PubMed Web of Science ®Google Scholar
• Li S, Whorton AR. Regulation of protein tyrosine phosphatase 1B in intact cells by S-nitrosothiols. Arch Biochem Biophys 2003;410:269–279.
   PubMedGoogle Scholar
• Gladwin MT, Wang X, Hogg N. Methodological vexation about thiol oxidation versus S-nitrosation - A commentary on “An ascorbate-dependent artifact that interferes with the interpretation of the biotin-switch assay”. Free Radic Biol Med 2006;41:557–561.
   Google Scholar
• Zhang Y, Keszler A, Broniowska KA, Hogg N. Characterization and application of the biotin-switch assay for the identification of S-nitrosated proteins. Free Radic Biol Med 2005;38:874–881.
   PubMed Web of Science ®Google Scholar
• Ying J, Clavreul N, Sethuraman M, Adachi T, Cohen RA. Thiol oxidation in signaling and response to stress: detection and quantification of physiological and pathophysiological thiol modifications. Free Radic Biol Med 2007;43: 1099–1108.
   PubMed Web of Science ®Google Scholar
• Wright SK, Viola RE. Evaluation of methods for the quantification of cysteines in proteins. Anal Biochem 1998; 265:8–14.
   PubMedGoogle Scholar
• Huang B, Chen C. An ascorbate-dependent artifact that interferes with the interpretation of the biotin switch assay. Free Radic Biol Med 2006;41:562–567.
   PubMed Web of Science ®Google Scholar
• Forrester MT, Foster MW, Stamler JS. Assessment and application of the biotin switch technique for examining protein S-nitrosylation under conditions of pharmacologically induced oxidative stress. J Biol Chem 2007;282:13977–13983.
   PubMedGoogle Scholar
• Landino LM, Koumas MT, Mason CE, Alston JA. Ascorbic acid reduction of microtubule protein disulfides and its relevance to protein S-nitrosylation assays. Biochem Biophys Res Commun 2006;340:347–352.
   Google Scholar
• Giustarina D, Dalle-Donne I, Colombo R, Milzani A, Rossi R. Is ascorbate able to reduce disulfide bridges? A cautionary note. Nitric Oxide 2008;19:252–258.
   Google Scholar
• Zhang Y, Hogg N. S-Nitrosothiols: cellular formation and transport. Free Radic Biol Med 2005; 38:831–838.
   PubMed Web of Science ®Google Scholar
• Holmes AJ, Williams DLH. Reaction of ascorbic acid with S-nitrosothiols: clear evidence for two distinct reaction pathways. J Chem Soc Perkin Trans 2 2000;1639–1644.
   Google Scholar
• Smith JN, Dasgupta TP. Kinetics and mechanism of the decomposition of S-nitrosoglutathione by L-ascorbic acid and copper ions in aqueous solution to produce nitric oxide. Nitric Oxide:Biol Chem 2000;4:57–66.
   PubMed Web of Science ®Google Scholar
• Wang X, Kettenhofen NJ, Shiva S, Hogg N, Gladwin MT. Copper dependence of the biotin switch assay: modified assay for measuring cellular and blood nitrosated proteins. Free Radic Biol Med 2008;44:1362–1372.
   PubMedGoogle Scholar
• Askew S, Barnett D, MCAninly D, Williams D. Catalysis by Cu2+ of nitric oxide release from S-nitrosothiols (RSNO). J Chem Soc Perkin Trans 2 1995; 741–745.
   Google Scholar
• Dicks AP, Swift HR, Williams DLH, Butler AR, Al-S´doni HH, Cox BG. Identification of Cu+ as the effective reagent in nitric oxide formation from S-nitrosothiols (RSNO). J Chem Soc Perkin Trans 2 1996;481–487.
   Google Scholar
• Kirsch M, Buscher AM, Aker S, Schulz R, de Groot H. New insights into the S-nitrosothiol-ascorbate reaction. The formation of nitroxyl. Org Biomol Chem 2009;7: 1954–1962.
   Google Scholar
• Sonnenschein K, de Groot H, Kirsch M. Formation of S-nitrosothiols from regiospecific reaction of thiols with N-nitrosotryptophan-derivatives. J Biol Chem 2004;279: 45433–45440.
   Google Scholar
• Marley R, Patel RP, Orie N, Ceaser E, Darley-Usmar V, Moore K. Formation of nanomolar concentrations of S-nitrosoalbumin in human plasma by nitric oxide. Free Radic Biol Med 2001;31:688–696.
   PubMed Web of Science ®Google Scholar
• Saville B. A scheme for the colorimetric determination of microgram amounts of thiols. Analyst 1958;83:670–672.
   Web of Science ®Google Scholar
• Noble DR, Williams DLH. Formation and reaction of S-nitroso proteins. J Chem Soc Perkin Trans 2 2001;13–17.
   Google Scholar
• Ellmann GL. A colorimetric method for determining low concentrations of mercaptans. Arch Biochem Biophys 1958; 74:443–450.
   PubMed Web of Science ®Google Scholar
• Eyer P, Worek F, Kiderlen D, Sinko G, Stuglin A, Simeon-Rudolf V, . Molar absorption coefficients for the reduced Ellman reagent: reassessment. Anal Biochem 2003; 312:224–227.
   PubMed Web of Science ®Google Scholar
• Riener CK, Kada G, Gruber HJ. Quick measurement of protein sulfhydryls with Ellman´s reagent and with 4, 4´-dithiodypyridine. Anal Bioanal Chem 2002;373:266–276.
   PubMed Web of Science ®Google Scholar
• Faulstich H, Tews P, Heintz D. Determination and derivatization of protein thiols by n-octyldithionitrobenzoic acid. Anal Biochem 1993;208:357–362.
   PubMed Web of Science ®Google Scholar
• Singh R, Blättler WA, Collinson AR. An amplified assay for thiols based on reactivation of papain. Anal Biochem 1993;213:49–56.
   PubMed Web of Science ®Google Scholar
• Aquart DV, Dasgupta TP. The reaction of S-nitroso-N-acetyl-D, L-penicillamine (SNAP) with the angiotensin converting enzyme inhibitor, captopril–mechanism of transnitrosation. Org Biomol Chem 2005;3:1640–1646.
   PubMed Web of Science ®Google Scholar
• Meyer DJ, Kramer H, Ozer N, Coles B, Ketterer B. Kinetics and equilibria of S-nitrosothiol-thiol exchange between glutathione, cysteine, penicilamines and serm albumin. FEBS Lett 1994;345:177–180.
   PubMed Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, . Gaussian 98W. Pittsburgh PA: Gaussian Inc. 2000.
   Google Scholar
• Barone V, Cossi M, Tomasi J. A new definition of cavities for the computation of solvation free energies by the polarizable continuum model. J Chem Phys 1997;107:3210–3221.
   Web of Science ®Google Scholar
• Kettenhofen NJ, Broniowska KA, Keszler A, Zhang Y, Hogg J. Proteomic methods for analysis of S-nitrosation. J Chromatogr B 2007;851:152–159.
   PubMed Web of Science ®Google Scholar
• Munro AP, Williams DLH. Reactivity of sulfur nucleophiles towards S-nitrosothiols. J Chem Soc Perkin Trans 2 2000;1794–1797.
   Google Scholar
• Munro AP, Williams DLH. Reactivity of nitrogen nucleophiles towards S-nitrosopenicillamine. J Chem Soc Perkin Trans 2 1999;1989–1993.
   Google Scholar
• Furst A, Berlo RC, Hooton S. Hydrazine as a reducing agent for organic compounds (catalytic hydrazine reductions). Chem Rev 1965;65:51–68.
   Web of Science ®Google Scholar
• Badrakhan CD, Petrat F, Holzhauser M, Fuchs A, Lomonosova EE, de Groot H, . The methanol method for the quantification of ascorbic acid and dehydroascorbic acid in biological samples. J Biochem Biophys Met 2004;58:207–218.
   PubMedGoogle Scholar
• Gowland RJ, Howes KR, Stedman G. Nitrogen-15 tracer evidence discounting the occurrence of a cyclic azide intermediate in the reaction between nitrous acid and hydrazine. J Chem Soc Dalton Trans 1992:797–799.
   Google Scholar
• Singh SP, Wishnok JS, Keshive M, Deen WM, Tannenbaum SR. The chemistry of the S-nitrosoglutatrhione/glutathione system. Proc Natl Acad Sci USA 1996;93: 14428–14433.
   PubMed Web of Science ®Google Scholar
• Lurker PA. Technical Documentary Report No. AMRL- TR-76–23. In Catalytic Deoxygenation of Aqueous Solution by Hydrazine., Aerospace Medical Research Laboratory, Wright-Patterson Air Force Base, Dayton, Ohio; 1976.
   Google Scholar
• MacNaughton MG, Urda GA, Bowden SE. Report No. CEEDO-TR-78–11. In Oxidation of Hydrazine in Aqueous Solutions, Civil and Environmental Engineering Development Office, Tyndall Air Force Base, Florida; 1978.
   Google Scholar
• Ellis SRM, Jeffreys GV, Hill P. Oxidation of hydrazine in aqueous solution. J Appl Chem 1960;10:347–352.
   Google Scholar
• Winterbourn CC, Metodiewa D. Reactivity of biologically important thiol compopunds with superoxide and hydrogen peroxide. Free Radic Biol Med 1999;27:322–328.
   PubMed Web of Science ®Google Scholar
• Gilbert EC. Studies on hydrazine. The Auto-Oxidation. J Am Chem Soc 1929;51:2744–2751.
   Google Scholar
• Audrieth LF, Mohr PH. Autoxidation of hydrazine. Effect of dissolved metals and deactivators. Ind Eng Chem 1951; 43:1774–1779.
   Google Scholar
• Gaunt H, Wetton EAM. The reaction between hydrazine and oxygen in water. J Appl Chem 1966;16:171–176.
   Google Scholar
• Hussain SM, Frazier JM. Cellular toxicity of hydrazine in primary rat hepatocytes. Toxicol Sci 2002;69:424–432.
   PubMed Web of Science ®Google Scholar
• Speit G, Wick C, Wolf M. Induction of sister chromatid exchanges by hydroxylamine, hydrazine and isoniazid and their inhibition by cysteine. Hum Genet 1980; 54:155–158.
   Google Scholar
• Gamberini M, Cidade MR, Valotta LA, Armelin MC, Leite LC. Contribution of hydrazines-derived alkyl- radicals to cytotoxicity and transformation induced in normal c-myc-overexpressing mouse fibroblasts. Carcinogenesis 1998;19:147–155.
   PubMed Web of Science ®Google Scholar
• Salgo MG, Bermudez E, Squadrito GL, Pryor WA. DNA Damage and oxidation of thiols peroxynitrite causes in rat thymocytes. Arch Biochem Biophys 1995;322:500–505.
   PubMed Web of Science ®Google Scholar
• Szacilowski K, Stasicka Z. S-Nitrosothiols: materials, reactivity and mechanisms. Prog React Kinet Mech 2001;26:1–58.
   Web of Science ®Google Scholar
• Markus G, Karush F. The disulfide bond of human serum albumin and bovine g-globulin. J Am Chem Soc 1957;79: 134–139.
   Google Scholar
• Era S, Kuwata K, Imai H, Nakamura K, Hayashi T, Sogami M. Age-related change in redox state of human serum albumin. Biochim Biophys Acta 1995;1247:12–16.
   PubMed Web of Science ®Google Scholar
• Era S, Hamaguchi T, Sogami M, Kuwata K, Suzuki E, Miura K, . Further studies on the resolution of human mercaptalbumin and non-mercaptalbumin and on human serum albumin in the elderly by high-performance liquid-chromatography. Int J Pept Protein Res 1988;31:435–442.
   Google Scholar
• Turell L, Botti H, Carballal S, Radi R, Alvarez B. Sulfenic acid – A key intermediate in albumin thiol oxidation. J Chromatogr B 2009;877:3384–3392.
   PubMed Web of Science ®Google Scholar