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

Recent studies distinguish the biological and pharmacological effects of nitroxyl (HNO) from its oxidized/deprotonated product nitric oxide (·NO), but the lack of HNO detection methods limits the understanding its in vivo mechanisms and the identification of endogenous sources. We previously demonst...

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Publicado en:Journal of the American Chemical Society Vol. 133; no. 30; pp. 11675 - 11686
Autores principales: Reisz, Julie A., Zink, Charles N., King, S. Bruce
Formato: Artículo
Publicado: American Chemical Society 8/3/2011
Materias:
Acceso en línea:Ver este registro en EBSCOhost
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      pub: American Chemical Society
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        65170115
        10.1021/ja203652z
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        atl: Rapid and Selective Nitroxyl (HNO) Trapping by Phosphines: Kinetics and New Aqueous Ligations for HNO Detection and Quantitation.
      aug:
        au:
          Reisz, Julie A.
          Zink, Charles N.
          King, S. Bruce
        affil:
          Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, United States
          Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, United States
      su:
        Nitric oxide
        Amides
        Biomarkers
        Nitrogen oxides
        Carbamates
        Urease
      sug:
        subj:
          Nitric oxide
          Amides
          Biomarkers
          Nitrogen oxides
          Carbamates
          Urease
      ab: Recent studies distinguish the biological and pharmacological effects of nitroxyl (HNO) from its oxidized/deprotonated product nitric oxide (·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.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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