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Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion

Miranda, Katarina M., Espey, Michael G., Yamada, Kenichi, Krishna, Murali, Ludwick, Natalie, Kim, SungMee, Jourd'heuil, David, Grisham, Matthew B., Feelisch, Martin, Fukuto, Jon M. and Wink, David A. (2001) Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion The Journal of Biological Chemistry, 276, (3), pp. 1720-1727. (doi:10.1074/jbc.M006174200). (PMID:11042174).

Record type: Article

Abstract

The nitroxyl anion (NO-) is a highly reactive molecule that may be involved in pathophysiological actions associated with increased formation of reactive nitrogen oxide species. Angeli's salt (Na2N2O3; AS) is a NO- donor that has been shown to exert marked cytotoxicity. However, its decomposition intermediates have not been well characterized. In this study, the chemical reactivity of AS was examined and compared with that of peroxynitrite (ONOO-) and NO/N2O3. Under aerobic conditions, AS and ONOO- exhibited similar and considerably higher affinities for dihydrorhodamine (DHR) than NO/N2O3. Quenching of DHR oxidation by azide and nitrosation of diaminonaphthalene were exclusively observed with NO/N2O3. Additional comparison of ONOO- and AS chemistry demonstrated that ONOO- was a far more potent one-electron oxidant and nitrating agent of hydroxyphenylacetic acid than was AS. However, AS was more effective at hydroxylating benzoic acid than was ONOO-. Taken together, these data indicate that neither NO/N2O3 nor ONOO- is an intermediate of AS decomposition. Evaluation of the stoichiometry of AS decomposition and O2 consumption revealed a 1:1 molar ratio. Indeed, oxidation of DHR mediated by AS proved to be oxygen-dependent. Analysis of the end products of AS decomposition demonstrated formation of NO2- and NO3- in approximately stoichiometric ratios. Several mechanisms are proposed for O2 adduct formation followed by decomposition to NO3- or by oxidation of an HN2O3- molecule to form NO2-. Given that the cytotoxicity of AS is far greater than that of either NO/N2O3 or NO + O2, this study provides important new insights into the implications of the potential endogenous formation of NO- under inflammatory conditions in vivo.

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Published date: 19 January 2001
Organisations: Clinical & Experimental Sciences

Identifiers

Local EPrints ID: 337873
URI: http://eprints.soton.ac.uk/id/eprint/337873
ISSN: 0021-9258
PURE UUID: 82dcd6b2-f3dc-4a78-98bf-7b276d7b037b
ORCID for Martin Feelisch: ORCID iD orcid.org/0000-0003-2320-1158

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Date deposited: 22 Jun 2012 15:40
Last modified: 18 Jul 2017 06:00

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Contributors

Author: Katarina M. Miranda
Author: Michael G. Espey
Author: Kenichi Yamada
Author: Murali Krishna
Author: Natalie Ludwick
Author: SungMee Kim
Author: David Jourd'heuil
Author: Matthew B. Grisham
Author: Martin Feelisch ORCID iD
Author: Jon M. Fukuto
Author: David A. Wink

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