Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide: Synthesis, kinetic, and stability studies

Gerald M. Rosen, Supatra Porasuphatana, Pei Tsai, Nicholas P. Ambulos, Valeri E. Galtsev, Kazuhiro Ichikawa, Howard J. Halpern

    Research output: Contribution to journalArticle

    24 Citations (Scopus)

    Abstract

    The in-vivo in-situ spin-trapping of NO. with iron chelates is limited in its ability to localize NO. at defined cellular compartments. Nitronyl nitroxides, such as 2-(4-carboxyphenyl)-4,4,5,5-tetramethylimidazoline 3-oxide 1-oxyl, have been found to react with NO.. The resulting nitroxide, 2-(4-carboxyphenyl)-4,4,5,5-tetramethylimidazolidine 1-oxyl, exhibits an EPR spectrum that is characteristically distinct from the parent nitroxide. However, nitronyl nitroxides are unstable in biologic milieu. This limits their ability to in vivo identify NO. at specific tissue compartments. Herein, we report on the preparation of a family of dendrimer-containing nitronyl nitroxides, which were developed to spin-trap NO.. Once synthesized, we determined their rate of reaction with NO. and their capacity to spin-trap NO. and estimated the stability of dendrimer-linked nitronyl nitroxides under various experimental paradigms. For the largest of the dendrimeric nitronyl nitroxides prepared, the reaction with NO. changed the EPR spectrum from one that was broad to that with a major component with narrow and defined spectral lines. These compounds promise to be excellent biological spin-trapping agents for NO..

    Original languageEnglish
    Pages (from-to)1021-1027
    Number of pages7
    JournalMacromolecules
    Volume36
    Issue number4
    DOIs
    Publication statusPublished - Feb 25 2003

    Fingerprint

    Dendrimers
    Nitric oxide
    Paramagnetic resonance
    Nitric Oxide
    Iron Chelating Agents
    Kinetics
    Tissue
    Iron
    Oxides
    1,3-dihydroxy-4,4,5,5-tetramethyl-2-(4-carboxyphenyl)tetrahydroimidazole

    All Science Journal Classification (ASJC) codes

    • Organic Chemistry
    • Polymers and Plastics
    • Inorganic Chemistry
    • Materials Chemistry

    Cite this

    Rosen, G. M., Porasuphatana, S., Tsai, P., Ambulos, N. P., Galtsev, V. E., Ichikawa, K., & Halpern, H. J. (2003). Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide: Synthesis, kinetic, and stability studies. Macromolecules, 36(4), 1021-1027. https://doi.org/10.1021/ma021292m

    Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide : Synthesis, kinetic, and stability studies. / Rosen, Gerald M.; Porasuphatana, Supatra; Tsai, Pei; Ambulos, Nicholas P.; Galtsev, Valeri E.; Ichikawa, Kazuhiro; Halpern, Howard J.

    In: Macromolecules, Vol. 36, No. 4, 25.02.2003, p. 1021-1027.

    Research output: Contribution to journalArticle

    Rosen, GM, Porasuphatana, S, Tsai, P, Ambulos, NP, Galtsev, VE, Ichikawa, K & Halpern, HJ 2003, 'Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide: Synthesis, kinetic, and stability studies', Macromolecules, vol. 36, no. 4, pp. 1021-1027. https://doi.org/10.1021/ma021292m
    Rosen GM, Porasuphatana S, Tsai P, Ambulos NP, Galtsev VE, Ichikawa K et al. Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide: Synthesis, kinetic, and stability studies. Macromolecules. 2003 Feb 25;36(4):1021-1027. https://doi.org/10.1021/ma021292m
    Rosen, Gerald M. ; Porasuphatana, Supatra ; Tsai, Pei ; Ambulos, Nicholas P. ; Galtsev, Valeri E. ; Ichikawa, Kazuhiro ; Halpern, Howard J. / Dendrimeric-containing nitronyl nitroxides as spin traps for nitric oxide : Synthesis, kinetic, and stability studies. In: Macromolecules. 2003 ; Vol. 36, No. 4. pp. 1021-1027.
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