Superoxide radical trapping and spin adduct decay of 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO): Kinetics and theoretical analysis

Frederick A. Villamena, Jay L. Zweier

Research output: Contribution to journalArticle

Abstract

Spin-trapping of oxygen-centered radicals such as superoxide radical is increasingly becoming important in the study of biological oxidations. Superoxide spin-trapping and decay kinetics in aqueous media of the new solid nitrone 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO) are reported and compared to those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO). Superoxide spin-trapping by BocMPO is significantly slower than that by DEPMPO and DMPO, and the half-life of BocMPO-superoxide adduct is shorter than that of DEPMPO-superoxide adduct. The BocMPO spin-trapping ability and stability of its superoxide adducts are rationalized based on theoretical calculations.

Original languageEnglish (US)
Pages (from-to)1340-1344
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number7
StatePublished - 2002

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Superoxides
Kinetics
Oxides
5-tert-butoxycarbonyl 5-methyl-1-pyrroline N-oxide
Reactive Oxygen Species
Oxidation
5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide
pyrroline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Superoxide radical trapping and spin adduct decay of 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO): Kinetics and theoretical analysis",
abstract = "Spin-trapping of oxygen-centered radicals such as superoxide radical is increasingly becoming important in the study of biological oxidations. Superoxide spin-trapping and decay kinetics in aqueous media of the new solid nitrone 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO) are reported and compared to those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO). Superoxide spin-trapping by BocMPO is significantly slower than that by DEPMPO and DMPO, and the half-life of BocMPO-superoxide adduct is shorter than that of DEPMPO-superoxide adduct. The BocMPO spin-trapping ability and stability of its superoxide adducts are rationalized based on theoretical calculations.",
author = "Villamena, {Frederick A.} and Zweier, {Jay L.}",
year = "2002",
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journal = "Journal of the Chemical Society, Perkin Transactions 2",
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T1 - Superoxide radical trapping and spin adduct decay of 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO)

T2 - Kinetics and theoretical analysis

AU - Villamena, Frederick A.

AU - Zweier, Jay L.

PY - 2002

Y1 - 2002

N2 - Spin-trapping of oxygen-centered radicals such as superoxide radical is increasingly becoming important in the study of biological oxidations. Superoxide spin-trapping and decay kinetics in aqueous media of the new solid nitrone 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO) are reported and compared to those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO). Superoxide spin-trapping by BocMPO is significantly slower than that by DEPMPO and DMPO, and the half-life of BocMPO-superoxide adduct is shorter than that of DEPMPO-superoxide adduct. The BocMPO spin-trapping ability and stability of its superoxide adducts are rationalized based on theoretical calculations.

AB - Spin-trapping of oxygen-centered radicals such as superoxide radical is increasingly becoming important in the study of biological oxidations. Superoxide spin-trapping and decay kinetics in aqueous media of the new solid nitrone 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BocMPO) are reported and compared to those of 5,5-dimethyl-1-pyrroline N-oxide (DMPO) and 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO). Superoxide spin-trapping by BocMPO is significantly slower than that by DEPMPO and DMPO, and the half-life of BocMPO-superoxide adduct is shorter than that of DEPMPO-superoxide adduct. The BocMPO spin-trapping ability and stability of its superoxide adducts are rationalized based on theoretical calculations.

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