Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2017 Mar 1:617:129-136.
doi: 10.1016/j.abb.2016.08.014. Epub 2016 Aug 20.

The chemical biology of HNO signaling

Christopher L Bianco  1 , John P Toscano  1 , Michael D Bartberger  2 , Jon M Fukuto  3
Affiliations
Review

The chemical biology of HNO signaling

Christopher L Bianco et al. Arch Biochem Biophys. .

Abstract

Nitroxyl (HNO) is a simple molecule with significant potential as a pharmacological agent. For example, its use in the possible treatment of heart failure has received recent attention due to its unique therapeutic properties. Recent progress has been made on the elucidation of the mechanisms associated with its biological signaling. Importantly, the biochemical mechanisms described for HNO bioactivity are consistent with its unique and novel chemical properties/reactivity. To date, much of the biology of HNO can be associated with interactions and modification of important regulatory thiol proteins. Herein will be provided a description of HNO chemistry and how this chemistry translates to some of its reported biological effects.

Keywords: Azanone; Nitrogen oxides; Nitroxyl; Thiols.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Reaction of HNO with thiols.
Figure 2
Figure 2
Electron pair repulsion with HNO/ROH and HNO/RSH adducts.
Figure 3
Figure 3
HNO-mediated modification of a thiol versus a persulfide and possible mechanism of reductive conversion of the adduct to the corresponding thiol.
Figure 4
Figure 4
Mechanism of HNO generation from NH2CN.
See this image and copyright information in PMC

References

    1. Basudhar D, Ridnour LA, Cheng R, Kesarwala AH, Heinecke J, Wink DA. Biological signaling by small inorganic molecules. Coord. Chem. Rev. 2016;306:708–723. - PMC - PubMed
    1. Fukuto JM, Carrington SJ. HNO Signaling Mechanisms. Antiox. Redox Signal. 2011;14(9):1649–1657. - PubMed
    1. Irvine JC, Ritchie RH, Favaloro JL, Andrews KL, Widdop RE, Kemp-Harper BK. Nitroxyl (HNO): The Ciderella of the nitric oxide story. Trends Pharmacol. Sci. 2008;29:601–608. - PubMed
    1. Shoman M, Aly OM. Nitroxyl (HNO): A reduced form of nitric oxide with distinct chemical, pharmacological, and therapeutic properties. Oxid. Med. Cellular Longevity. 2016 2016, ID 4867124, 15 pages. - PMC - PubMed
    1. Miranda KM, Nagasawa HT, Toscano JP. Donors of HNO. Curr. Top. Med. Chem. 2005;5:649–664. - PubMed

LinkOut - more resources