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Comparison of the NO and HNO donating properties of diazeniumdiolates: Primary amine adducts release HNO in vivo

  1. Author:
    Miranda, K. M.
    Katori, T.
    de Holding, C. L. T.
    Thomas, L.
    Ridnour, L. A.
    MeLendon, W. J.
    Cologna, S. M.
    Dutton, A. S.
    Champion, H. C.
    Mancardi, D.
    Tocchetti, C. G.
    Saavedra, J. E.
    Keefer, L. K.
    Houk, K. N.
    Fukuto, J. M.
    Kass, D. A.
    Paolocci, N.
    Wink, D. A.

  2. Author Address

    Univ Arizona, Dept Chem, Tucson, AZ 85721 USA. Johns Hopkins Med Inst, Div Cardiol, Dept Med, Baltimore, MD 21287 USA. Johns Hopkins Med Inst, Div Cardiol, Dept Biomed Engn, Baltimore, MD 21287 USA. NCI, Tumor Biol Sect, Radiat Biol Radiat, NIH, Bethesda, MD 20892 USA. Univ Calif Los Angeles, Ctr Hlth Sci, Dept Chem & Biochem, Los Angeles, CA 90095 USA. Univ Calif Los Angeles, Ctr Hlth Sci, Dept Mol & Med Pharmacol, Los Angeles, CA 90095 USA. SAIC Frederick, Basic Res Program, Frederick, MD 21702 USA. NCI, Comparat Carcinogenesis Lab, Frederick, MD 21702 USA Miranda, KM, Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
    1. Year: 2005
    2. Date: DEC 29
  2. Journal: Journal of Medicinal Chemistry
    1. 48
    2. 26
    3. Pages: 8220-8228
  4. Type of Article: Article
  1. Abstract:

    Diazeniumdiolates, more commonly referred to as NONOates, have been extremely useful in the investigation of the biological effects of nitric oxide (NO) and related nitrogen oxides. The NONOate Angell's salt (Na2N2O3) releases nitroxyl (HNO) under physiological conditions and exhibits unique cardiovascular features (i.e., positive inotropy/lusitropy) that may have relevance for pharmacological treatment of heart failure. In the search for new, organic-based compounds that release HNO, we examined isopropylamine NONOate (IPA/NO; Na[(CH3)(2)CHNH(N(O)NO]), which is an adduct of NO and a primary amine. The chemical and pharmacological properties of IPA/NO were compared to those of Angeli's salt and a NO-producing NONOate, DEA/NO (Na[Et2NN(O)NO]), which is a secondary amine adduct. Under physiological conditions IPA/NO exhibited all the markers of HNO production (e.g., reductive nitrosylation, thiol reactivity, positive inotropy). These data suggest that primary amine NONOates may be useful as HNO donors in complement to the existing series of secondary amine NONOates, which are well-characterized NO donors

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  2. WOS: 000234301800014

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