Thermal decomposition of oxyhyponitrite (sodium trioxodinitrate(II)) in aqueous solution

Bonner, Francis T.; Ravid, B.

doi:10.1021/ic50145a022

Cited by 114 publications

(97 citation statements)

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“…1, panel A compared with B, and Fig. 4D) (28,29). Furthermore, GSH and Fe III -MGD, which are efficient scavengers of HNO, markedly inhibited the hydroxylation of phenol (data not shown).…”

Section: Discussionmentioning

confidence: 88%

“…The decomposition of 3a is especially fast in aqueous solutions with pH 6 -13 (30,31), which most likely reflects shifts in the equilibrium between 3a and 3b in favor of the latter (Scheme 1). Bonner and Ravid (29) 2 Ϫ , implying that this process follows the reaction sequence presented in Scheme 1 (29). However, these authors noted that the proportions of 15 N in the reaction products were different at pH 5.0, suggesting that some modification of pathway cannot be ruled out.…”

Section: Methodsmentioning

confidence: 95%

“…Thereafter, additions to the final reaction solution were made through the septum of the corresponding vial using a 0.10-ml gas-tight syringe. (29)). The latter species can dimerize to cis-hyponitrous acid (3a), which is unstable and decomposes to N 2 O and H 2 O.…”

Section: Methodsmentioning

confidence: 99%

“…However, these authors noted that the proportions of 15 N in the reaction products were different at pH 5.0, suggesting that some modification of pathway cannot be ruled out. At pH Ͻ 4, the decomposition rate of 1a increases with increasing acidity with production of NO ⅐ (28,29).…”

Section: Methodsmentioning

confidence: 99%

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Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate

Ivanova

Salama

Clancy

et al. 2003

Journal of Biological Chemistry

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Despite its negative redox potential, nitroxyl (HNO) can trigger reactions of oxidation. Mechanistically, these reactions were suggested to occur with the intermediate formation of either hydroxyl radical ( ⅐ OH) or peroxynitrite (ONOO ؊ ). In this work, we present further experimental evidence that HNO can generate ⅐ OH. Sodium trioxodinitrate (Na 2 N 2 O 3 ), a commonly used donor of HNO, oxidized phenol and Me 2 SO to benzene diols and ⅐ CH 3 , respectively. The oxidation of Me 2 SO was O 2 -independent, suggesting that this process reflected neither the intermediate formation of ONOO ؊ nor a redox cycling of transition metal ions that could initiate Fenton-like reactions. In solutions of phenol, Na 2 N 2 O 3 yielded benzene-1,2-diol and benzene-1,4-diol at a ratio of 2:1, which is consistent with the generation of free ⅐ OH. Ethanol and Me 2 SO, which are efficient scavengers of ⅐ OH, impeded the hydroxylation of phenol. A mechanism for the hydrolysis of Na 2 N 2 O 3 is proposed that includes dimerization of HNO to cis-hyponitrous acid (HO-N‫؍‬N-OH) with a concomitant azo-type homolytic fission of the latter to N 2 and ⅐ OH. The HNO-dependent production of ⅐ OH was with 1 order of magnitude higher at pH 6.0 than at pH 7.4. Hence, we hypothesized that HNO can exert selective toxicity to cells subjected to acidosis. In support of this thesis, Na 2 N 2 O 3 was markedly more toxic to human fibroblasts and SK-N-SH neuroblastoma cells at pH 6.2 than at pH 7.4. Scavengers of ⅐ OH impeded the cytotoxicity of Na 2 N 2 O 3 . These results suggest that the formation of HNO may be viewed as a toxicological event in tissues subjected to acidosis.The biochemistry of nitroxyl (HNO) has attracted considerable interest in recent years. In cells, the biosynthesis of HNO is believed to proceed via reduction of NO ⅐ by superoxide dismutase (1) and cytochrome c (2), and reduction of S-nitrosoglutathione by low molecular weight and protein thiols (3-5). It has been suggested that HNO can affect the etiology of various pathophysiological conditions such as inflammation and neurodegenerative diseases, especially when H 2 O 2 and transition metal ions are present (6, 7). Similar to NO ⅐ and NO ϩ , HNO is a potent inducer of the antioxidant protein heme oxygenase 1 (8), exhibits vasorelaxant properties (9), and modulates the activity of thiol-containing proteins, such as aldehyde dehydrogenase (10, 11) and the N-methyl-D-aspartate receptor (12, 13). In in vivo experiments, Paolocci et al. (14) observed that HNO exerts positive inotropic and lusitropic action, which unlike NO ⅐ and nitrates is independent and additive to ␤-adrenergic stimulation and increases the release of plasma calcitonin gene-related peptide; these results suggest that donors of HNO are potential prodrugs for the treatment of heart failure (14). At high doses, HNO has been shown to induce DNA singlestrand breakage (15, 16) and a concentration-dependent cytotoxicity in murine thymocytes (16). This cytotoxicity was associated with activation of the nuclear nick sen...

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“…1, panel A compared with B, and Fig. 4D) (28,29). Furthermore, GSH and Fe III -MGD, which are efficient scavengers of HNO, markedly inhibited the hydroxylation of phenol (data not shown).…”

Section: Discussionmentioning

confidence: 88%

Section: Methodsmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate

Ivanova

Salama

Clancy

et al. 2003

Journal of Biological Chemistry

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show abstract

“…As mentioned previously, the rate of Angeli's salt decomposition in aqueous solution (i.e., rate of disappearance of the salt in solution) is pH independent in the pH 4-8 range [19,31]. However, there does not appear to be any report on the relative ratios of the N 2 O and NO gases generated as a function of pH.…”

Section: Methodsmentioning

confidence: 92%

Simultaneous Gas-phase Detection of Nitric Oxide (NO) and Nitrous Oxide (N2O) from the Decomposition of Angeli's Salt (Na2N2O3) at Different pHs Using Tunable-diode Laser Absorption Spectroscopy

Yi¹,

Namjou²,

McCann³

et al. 2009

Am. J. Biomed. Sci.

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Nitric oxide (NO) is a gaseous diatomic molecule that is biosynthesized in mammals, and it regulates a host of physiological processes including blood pressure. Over the last several years, there has been an increased interest in the redox partner HNO and its identifiable dimerization product N 2 O. This latter gaseous species is also the product of various NO-coupling reactions as occurs in bacterial NO-detoxification processes. An attractive new tool will be the ability to simultaneously detect NO and N 2 O from the same reaction vessel. We demonstrate proof-of-concept methodology for such a simultaneous and specific NO and N 2 O detection from the same precursor (from Angeli's salt decomposition) using tunable diode laser absorption spectroscopy without the need for separation or pretreatment of these gases.

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By Redox Reactions of Nitrogen Compounds (Not Including O ₂ or O ₃ )

Bonner¹

1991

Inorganic Reactions and Methods

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Thermal decomposition of oxyhyponitrite (sodium trioxodinitrate(II)) in aqueous solution

Cited by 114 publications

References 2 publications

Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate

Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate

Simultaneous Gas-phase Detection of Nitric Oxide (NO) and Nitrous Oxide (N2O) from the Decomposition of Angeli's Salt (Na2N2O3) at Different pHs Using Tunable-diode Laser Absorption Spectroscopy

By Redox Reactions of Nitrogen Compounds (Not Including O ₂ or O ₃ )

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Thermal decomposition of oxyhyponitrite (sodium trioxodinitrate(II)) in aqueous solution

Cited by 114 publications

References 2 publications

Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate

Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate

Simultaneous Gas-phase Detection of Nitric Oxide (NO) and Nitrous Oxide (N2O) from the Decomposition of Angeli's Salt (Na2N2O3) at Different pHs Using Tunable-diode Laser Absorption Spectroscopy

By Redox Reactions of Nitrogen Compounds (Not Including O 2 or O 3 )

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By Redox Reactions of Nitrogen Compounds (Not Including O ₂ or O ₃ )