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Rapid and Selective Nitroxyl (HNO) Trapping by Phosphines: Kinetics and New Aqueous Ligations for HNO Detection and Quantitation

  1. Author:
    Reisz, J. A.
    Zink, C. N.
    King, S. B.

  2. Author Address

    [Reisz, JA; King, SB] Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA. [Zink, CN] NCI, Chem Sect, Comparat Carcinogenesis Lab, Frederick, MD 21702 USA.;King, SB (reprint author), Wake Forest Univ, Dept Chem, Winston Salem, NC 27109 USA;kingsb@wfu.edu
    1. Year: 2011
    2. Date: Aug
  2. Journal: Journal of the American Chemical Society
    1. 133
    2. 30
    3. Pages: 11675-11685
  4. Type of Article: Article
  5. ISSN: 0002-7863
  1. Abstract:

    Recent studies distinguish the biological and pharmacological effects of nitroxyl (HNO) from its oxidized/deprotonated product nitric oxide (center dot NO), but the lack of HNO detection methods limits the understanding its in vivo mechanisms and the identification of endogenous sources. We previously demonstrated that reaction of HNO with triarylphosphines provides aza-ylides and HNO-derived amides, which may serve as stable HNO biomarkers. We now report a kinetic analysis for the trapping of HNO by phosphines, ligations of enzyme-generated HNO, and compatibility studies illustrating the selectivity of phosphines for HNO over other physiologically relevant nitrogen oxides. Quantification of HNO using phosphines is demonstrated using an HPLC-based assay and ligations of phosphine carbamates generate HNO-derived ureas. These results further demonstrate the potential of phosphine probes for reliable biological detection and quantification of HNO.

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External Sources

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  2. DOI: 10.1021/ja203652z
  3. View record in Web of Science®
  4. WOS: 000293872800048

Library Notes

  1. Fiscal Year: FY2010-2011
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