Elsevier

Biochemical Pharmacology

Volume 43, Issue 3, 4 February 1992, Pages 607-613
Biochemical Pharmacology

Chemical oxidation of N-hydroxyguanidine compounds: Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation

https://doi.org/10.1016/0006-2952(92)90584-6Get rights and content

Abstract

Nω-Hydroxy-l-arginine was found to cause vasodilation in arginine-depleted rabbit aorta. It is, therefore, likely to be a biosynthetic intermediate in the conversion of arginine to nitric oxide in this tissue. N-Hydroxyalkylguanidine compounds, including Nω-hydroxy-l-arginine, were oxidized with various oxidizing agents and examined for their ability to release nitric oxide. All oxidizing agents tested were capable of oxidizing the N-hydroxyguanidine function but only lead tetra-acetate (Pb(OAc)4) and potassium ferricyanide/hydrogen peroxide (K3FeCN6/H2O2) were capable of generating significant amounts of nitric oxide. Oxidation with K3FeCN6, lead oxide (PbO2) and silver carbonate (Ag2CO3) resulted instead in the release of nitrous oxide (N2O) presumably through the initial release of nitroxyl (HNO).

References (18)

There are more references available in the full text version of this article.

Cited by (119)

  • Quantification of intracellular HNO delivery with capillary zone electrophoresis

    2022, Nitric Oxide - Biology and Chemistry
    Citation Excerpt :

    Although nitric oxide (NO) was identified as the primary stimulator of soluble guanylyl cyclase (sGC), HNO can induce moderate activity [10]. In fact, NO synthase (NOS) has been suggested to produce HNO under hypoxic or low cofactor conditions or by oxidative degradation of the intermediate Nω-hydroxy-l-arginine [11–19]. While HNO and NO form a redox couple, direct interconversion is likely limited (see Ref. [20]).

  • Fluorescent probes for the detection of nitroxyl (HNO)

    2018, Free Radical Biology and Medicine
  • Is Azanone Endogenously Produced in Mammals?

    2017, The Chemistry and Biology of Nitroxyl (HNO)
  • Detection of HNO by Membrane Inlet Mass Spectrometry

    2017, The Chemistry and Biology of Nitroxyl (HNO)
  • Mechanistic Aspects of HNO Production from Hydroxylamine and Derivatives

    2016, The Chemistry and Biology of Nitroxyl (HNO)
View all citing articles on Scopus

Present address; CIPEIN, CITEFA, Zufriategui 4380, 1603 Villa Martelli, PCIA, Buenos Aires, Argentina.

View full text