Discriminative EPR detection of NO and HNO by encapsulated nitronyl nitroxides

References

• Shafirovich V, Lymar SV. Nitroxyl and its anion in aqueous solutions: spin states, protic equilibria, and reactivities toward oxygen and nitric oxide. Proc Natl Acad Sci USA2002;99: 7340–7345.
   PubMed Web of Science ®Google Scholar
• Bartberger MD, Liu W, Ford E, Miranda KM, Switzer C, Fukuto JM, . The reduction potential of nitric oxide (NO) and its importance to NO biochemistry. Proc Natl Acad Sci USA 2002;99:10958–10963.
   PubMed Web of Science ®Google Scholar
• Norris AJ, Sartippour MR, Lu M, Park T, Rao JY, Jackson MI, . Nitroxyl inhibits breast tumor growth and angiogenesis. Int J Cancer 2008;122:1905–1910.
   Google Scholar
• Paolocci N, Jackson MI, Lopez BE, Miranda K, Tocchetti CG, Wink DA, . The pharmacology of nitroxyl (HNO) and its therapeutic potential: not just the Janus face of NO. Pharmacol Ther 2007;113:442–458.
   Google Scholar
• Paolocci N, Katori T, Champion HC, St John ME, Miranda KM, Fukuto JM, . Positive inotropic and lusitropic effects of HNO/NO- in failing hearts: independence from beta-adrenergic signaling. Proc Natl Acad Sci USA 2003;100:5537–5542.
   Google Scholar
• Pagliaro P, Mancardi D, Rastaldo R, Penna C, Gattullo D, Miranda KM, . Nitroxyl affords thiol-sensitive myocardial protective effects akin to early preconditioning. Free Radic Biol Med 2003;34:33–43.
   Google Scholar
• Miranda KM, Paolocci N, Katori T, Thomas DD, Ford E, Bartberger MD, . A biochemical rationale for the discrete behavior of nitroxyl and nitric oxide in the cardiovascular system. Proc Natl Acad Sci USA 2003;100:9196–9201.
   PubMed Web of Science ®Google Scholar
• Wink DA, Miranda KM, Katori T, Mancardi D, Thomas DD, Ridnour L, . Orthogonal properties of the redox siblings nitroxyl and nitric oxide in the cardiovascular system: a novel redox paradigm. Am J Physiol Heart Circ Physiol 2003;285:H2264–2276.
   Google Scholar
• Fukuto JM, Jackson MI, Kaludercic N, Paolocci N. Examining nitroxyl in biological systems. Methods Enzymol 2008;440: 411–431.
   Google Scholar
• Irvine JC, Ritchie RH, Favaloro JL, Andrews KL, Widdop RE, Kemp-Harper BK. Nitroxyl (HNO): the Cinderella of the nitric oxide story. Trends Pharmacol Sci 2008;29:601–608.
   Google Scholar
• Miranda KM. The chemistry of nitroxyl (HNO) and implications in biology. Coord Chem Rev 2005;249:433–455.
   Web of Science ®Google Scholar
• Ishimura Y, Gao YT, Panda SP, Roman LJ, Masters BS, Weintraub ST. Detection of nitrous oxide in the neuronal nitric oxide synthase reaction by gas chromatography-mass spectrometry. Biochem Biophys Res Commun 2005;338:543–549.
   Google Scholar
• Cho JY, Dutton A, Miller T, Houk KN, Fukuto JM. Oxidation of N-hydroxyguanidines by copper(II): model systems for elucidating the physiological chemistry of the nitric oxide biosynthetic intermediate N-hydroxyl-L-arginine. Arch Biochem Biophys 2003;417:65–76.
   Google Scholar
• Fukuto JM, Dutton AS, Houk KN. The chemistry and biology of nitroxyl (HNO): a chemically unique species with novel and important biological activity. Chembiochem 2005;6:612–619.
   Google Scholar
• Doyle MP, Mahapatro SN, Broene RD, Guy JK. Oxidation and reduction of hemoproteins by trioxodinitrate(II). The role of nitrosyl hydride and nitrite. J Am Chem Soc 1988;110:593–599.
   Google Scholar
• Marti MA, Bari SE, Estrin DA, Doctorovich F. Discrimination of nitroxyl and nitric oxide by water-soluble Mn(III) porphyrins. J Am Chem Soc 2005;127:4680–4684.
   Google Scholar
• Xia Y, Cardounel AJ, Vanin AF, Zweier JL. Electron paramagnetic resonance spectroscopy with N-methyl-D-glucamine dithiocarbamate iron complexes distinguishes nitric oxide and nitroxyl anion in a redox-dependent manner: applications in identifying nitrogen monoxide products from nitric oxide synthase. Free Radic Biol Med 2000;29:793–797.
   Google Scholar
• Donzelli S, Espey MG, Thomas DD, Mancardi D, Tocchetti CG, Ridnour LA, . Discriminating formation of HNO from other reactive nitrogen oxide species. Free Radic Biol Med 2006;40: 1056–1066.
   Google Scholar
• Cline MR, Tu C, Silverman DN, Toscano JP. Detection of nitroxyl (HNO) by membrane inlet mass spectrometry. Free Radic Biol Med 2011;50:1274–1279.
   Google Scholar
• Rosenthal J, Lippard SJ. Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex. J Am Chem Soc 2010;132:5536–5537.
   PubMed Web of Science ®Google Scholar
• Reisz JA, Zink CN, King SB. Rapid and selective nitroxyl (HNO) trapping by phosphines: kinetics and new aqueous ligations for HNO detection and quantitation. J Am Chem Soc 2011;133:11675–11685.
   Google Scholar
• Akaike T, Yoshida M, Miyamoto Y, Sato K, Kohno M, Sasamoto K, . Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor/.NO through a radical reaction. Biochemistry 1993;32:827–832.
   PubMed Web of Science ®Google Scholar
• Yoshida M, Akaike T, Wada Y, Sato K, Ikeda K, Ueda S, Maeda H. Therapeutic effects of imidazolineoxyl N-oxide against endotoxin shock through its direct nitric oxide-scavenging activity. Biochem Biophys Res Commun 1994;202: 923–930.
   PubMed Web of Science ®Google Scholar
• Mitaka C, Hirata Y, Yokoyama K, Nagura T, Tsunoda Y, Amaha K. Beneficial effect of carboxy-PTIO on hemodynamic and blood gas changes in septic shock dogs. Crit Care 1997; 1:45–50.
   Google Scholar
• Konorev EA, Tarpey MM, Joseph J, Baker JE, Kalyanaraman B. S-nitrosoglutathione improves functional recovery in the isolated rat heart after cardioplegic ischemic arrest-evidence for a cardioprotective effect of nitric oxide. J Pharmacol Exp Ther 1995;274:200–206.
   PubMed Web of Science ®Google Scholar
• Cabrales P, Tsai AG, Intaglietta M. Nitric oxide regulation of microvascular oxygen exchange during hypoxia and hyperoxia. J Appl Physiol 2006;100:1181–1187.
   PubMed Web of Science ®Google Scholar
• Pieper GM, Siebeneich W. Use of a nitronyl nitroxide to discriminate the contribution of nitric oxide radical in endothelium-dependent relaxation of control and diabetic blood vessels. J Pharmacol Exp Ther 1997;283:138–147.
   Google Scholar
• Joseph J, Kalyanaraman B, Hyde JS. Trapping of nitric oxide by nitronyl nitroxides: an electron spin resonance investigation. Biochem Biophys Res Commun 1993;192:926–934.
   PubMed Web of Science ®Google Scholar
• Woldman Y, Khramtsov VV, Grigor’ev IA, Kiriljuk IA, Utepbergenov DI. Spin trapping of nitric oxide by nitronylnitroxides: measurement of the activity of no synthase from rat cerebellum. Biochem Biophys Res Commun 1994;202:195–203.
   PubMed Web of Science ®Google Scholar
• Akaike T, Maeda H. Quantitation of nitric oxide using 2- phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide (PTIO). Methods Enzymol 1996;268:211–221.
   PubMed Web of Science ®Google Scholar
• Az-ma T, Fujii K, Yuge O. Reaction between imidazolineoxil N-oxide (carboxy-PTIO) and nitric oxide released from cultured endothelial cells: quantitative measurement of nitric oxide by ESR spectrometry. Life Sci 1994;54:PL185–190.
   Google Scholar
• Bobko AA, Bagryanskaya EG, Reznikov VA, Kolosova NG, Clanton TL, Khramtsov VV. Redox-sensitive mechanism of no scavenging by nitronyl nitroxides. Free Radic Biol Med 2004;36:248–258.
   PubMed Web of Science ®Google Scholar
• Goldstein S, Russo A, Samuni A. Reactions of PTIO and carboxy-PTIO with *NO, *NO2, and O2-*. J Biol Chem 2003; 278:50949–50955.
   PubMed Web of Science ®Google Scholar
• Huang J, Sommers EM, Kim-Shapiro DB, King SB. Horseradish peroxidase catalyzed nitric oxide formation from hydroxyurea. J Am Chem Soc 2002;124:3473–3480.
   PubMed Web of Science ®Google Scholar
• Samuni U, Samuni Y, Goldstein S. On the Distinction between nitroxyl and nitric oxide using nitronyl nitroxides. J Am Chem Soc 2010;132:8428–8432.
   PubMed Web of Science ®Google Scholar
• Hrabie JA, Klose JR, Wink DA, Keefer LK. New nitric oxide-releasing zwitterions derived from polyamines. J Org Chem 1993;58:1472–1476.
   Web of Science ®Google Scholar
• Chao S, Simon RA, Mallouk TE, Wrighton MS. Multicomponent redox catalysts for reduction of large biological molecules using molecular hydrogen as the reductant. J Am Chem Soc 1988;110:2270–2276.
   Web of Science ®Google Scholar
• MacDonald RC, MacDonald RI, Menco BPM, Takeshita K, Subbarao NK, Hu LR. Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim Biophys Acta 1991;1061:297–303.
   PubMed Web of Science ®Google Scholar
• Hughes MN, Wimbledon PE. The chemisry of trioxodinitrates. Part I. Decompostion of sodium trioxodinitrate (Angeli’s salt) in aqueous solution. J Chem Soc Dalton Trans 1976; 703–707.
   Google Scholar
• Bonner FT, Dzelzkalns LS, Bonucci JA. Properties of nitroxyl as intermediate in the nitric oxide-hydroxylamine reaction and in trioxodinitrate decomposition. Inorgan Chem 1978; 17:2487–2494.
   Google Scholar
• Goldstein S, Samuni A, Russo A. Reaction of cyclic nitroxides with nitrogen dioxide: the intermediacy of the oxoammonium cations. J Am Chem Soc 2003;125:8364–8370.
   PubMedGoogle Scholar
• Singh RJ, Hogg N, Joseph J, Konorev E, Kalyanaraman B. The Peroxynitrite generator, SIN-1, becomes a nitric oxide donor in the presence of electron acceptors. Arch Biochem Biophys 1999;361:331–339.
   PubMed Web of Science ®Google Scholar
• Murphy ME, Sies H. Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase. Proc Natl Acad Sci USA 1991;88:10860–10864.
   PubMed Web of Science ®Google Scholar
• Jackson MI, Han TH, Serbulea L, Dutton A, Ford E, Miranda KM, . Kinetic feasibility of nitroxyl reduction by physiological reductants and biological implications. Free Radic Biol Med 2009;47:1130–1139.
   PubMed Web of Science ®Google Scholar
• Haseloff RF, Zollner S, Kirilyuk IA, Grigor’ev IA, Reszka R, Bernhardt R, . Superoxide-mediated reduction of the nitroxide group can prevent detection of nitric oxide by nitronyl nitroxides. Free Radic Res 1997;26:7–17.
   PubMed Web of Science ®Google Scholar
• Woldman YY, Semenov SV, Bobko AA, Kirilyuk IA, Polienko JF, Voinov MA, . Design of liposome-based pH sensitive nanoSPIN probes: nano-sized particles with incorporated nitroxides. Analyst 2009;134:904–910.
   Google Scholar
• Yelinova VI, Bobko AA, Mazhukin DG, Markel AL, Khramtsov VV. New donors and acceptors of nitrogen oxide as potential therapeutic agents. Russ J Bioorg Chem 2003;29:395–401.
   Google Scholar