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ESR Spin Trapping of the Reaction Between Urate and Peroxynitrite: the Hydrogen Adduct

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Abstract

Under basic conditions, the hydrogen adduct of the spin traps N-t-butyl-phenylnitrone (PBN) and α-(4-pyridyl-1-oxide)-N-t-butylnitrone (POBN) is formed as a major product in the reaction between the urate anion or dianion and peroxynitrite. It shows a characteristic nine-line spectrum with an intensity pattern of (1:2:1:1:2:1:1:2:1) and hyperfine splitting constants of a(H) = 10.68 G (two magnetically equivalent protons) and a(N) = 16.64 G. The hydrogen adduct of PBN also forms in the absence of urate. In this case, its formation is proposed to follow the non-traditional “inverted spin trapping” mechanism, followed by electron transfer between spin traps and the PBN–OH (or POBN–OH) adduct or one of its decomposition products. The H adduct formation is amplified when uric acid and peroxynitrite are present. Different yields of H adducts obtained from various spin traps supported the inverted spin trapping mechanism and can be rationalized by the relative redox potential of the spin traps.

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Acknowledgments

This work was financially supported by the National Science Foundation (CHE-0809725). We also acknowledge helpful discussions with Dr. William Dolbier, Jr.

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Authors and Affiliations

  1. Department of Chemistry, University of Florida, Box 117200, Gainesville, FL, 32611-7200, USA

    Witcha Imaram & Alexander Angerhofer

  2. Division of Nephrology, Hypertension and Renal Transplantation, Department of Medicine, University of Florida, Box 100224, Gainesville, FL, 32610, USA

    Richard J. Johnson

  3. Division of Renal Diseases and Hypertension, University of Colorado Health Science Center, Box C-281, 4200 E 9th Ave, Denver, CO, 80262, USA

    Richard J. Johnson

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  1. Witcha Imaram
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  2. Richard J. Johnson
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Correspondence to Alexander Angerhofer.

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Imaram, W., Johnson, R.J. & Angerhofer, A. ESR Spin Trapping of the Reaction Between Urate and Peroxynitrite: the Hydrogen Adduct. Appl Magn Reson 37, 463–472 (2010). https://doi.org/10.1007/s00723-009-0098-z

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  • DOI: https://doi.org/10.1007/s00723-009-0098-z

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