Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap

Micaël Hardy, A. Rockenbauer, Jeannette Vásquez-Vivar, Christopher Felix, Marcos Lopez, Satish Srinivasan, Narayan Avadhani, Paul Tordo, B. Kalyanaraman

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

We report here the detection and characterization of spin adducts formed from the trapping of reactive oxygen species (superoxide and hydroxyl radicals) and glutathiyl and carbon-centered radicals by a newly synthesized nitrone, Mito-DEPMPO. This is a cationic nitrone spin trap with a triphenyl phosphonium cation conjugated to the DEPMPO analogue. The Mito-DEPMPO-OOH adduct, formed from the trapping of superoxide by Mito-DEPMPO, was enzymatically generated using xanthine/xanthine oxidase and neuronal nitric oxide synthase, and chemically generated by KO2 in 18-crown-6. The Mito-DEPMPO-OOH adduct exhibits an eight-line EPR spectrum with partial asymmetry arising from the alternate line-width effect. The half-life of the Mito-DEPMPO-OOH adduct is 2-2.5-times greater than that of the DEPMPO-OOH. The Mito-DEPMPO-SG adduct, formed from the trapping of glutathiyl radicals by Mito-DEPMPO, is 3-times more persistent than the analogue DEPMPO-SG adduct. In this study, we describe the EPR characterization of spin adducts formed from Mito-DEPMPO. The EPR parameters of Mito-DEPMPO adducts are distinctly different and highly characteristic. The detection of superoxide from an intact mitochondrion was feasible with Mito-DEPMPO but not with DEPMPO. We conclude that Mito-DEPMPO nitrone and its analogues are more effective than most nitrone spin traps for trapping superoxide, hydroxyl, and thiyl radicals formed in biological systems, including mitochondria.

Original languageEnglish
Pages (from-to)1053-1060
Number of pages8
JournalChemical Research in Toxicology
Volume20
Issue number7
DOIs
Publication statusPublished - Jul 2007

Fingerprint

Superoxides
Paramagnetic resonance
Mitochondria
Kinetics
Hydroxyl Radical
Spin Trapping
Nitric Oxide Synthase Type I
Xanthine
Xanthine Oxidase
Biological systems
Linewidth
Half-Life
Cations
Reactive Oxygen Species
Carbon
nitrones

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Toxicology
  • Health, Toxicology and Mutagenesis

Cite this

Hardy, M., Rockenbauer, A., Vásquez-Vivar, J., Felix, C., Lopez, M., Srinivasan, S., ... Kalyanaraman, B. (2007). Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap. Chemical Research in Toxicology, 20(7), 1053-1060. https://doi.org/10.1021/tx700101d

Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap. / Hardy, Micaël; Rockenbauer, A.; Vásquez-Vivar, Jeannette; Felix, Christopher; Lopez, Marcos; Srinivasan, Satish; Avadhani, Narayan; Tordo, Paul; Kalyanaraman, B.

In: Chemical Research in Toxicology, Vol. 20, No. 7, 07.2007, p. 1053-1060.

Research output: Contribution to journalArticle

Hardy, M, Rockenbauer, A, Vásquez-Vivar, J, Felix, C, Lopez, M, Srinivasan, S, Avadhani, N, Tordo, P & Kalyanaraman, B 2007, 'Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap', Chemical Research in Toxicology, vol. 20, no. 7, pp. 1053-1060. https://doi.org/10.1021/tx700101d
Hardy, Micaël ; Rockenbauer, A. ; Vásquez-Vivar, Jeannette ; Felix, Christopher ; Lopez, Marcos ; Srinivasan, Satish ; Avadhani, Narayan ; Tordo, Paul ; Kalyanaraman, B. / Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap. In: Chemical Research in Toxicology. 2007 ; Vol. 20, No. 7. pp. 1053-1060.
@article{f895caa7c1094ab380c2204e3f85350f,
title = "Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap",
abstract = "We report here the detection and characterization of spin adducts formed from the trapping of reactive oxygen species (superoxide and hydroxyl radicals) and glutathiyl and carbon-centered radicals by a newly synthesized nitrone, Mito-DEPMPO. This is a cationic nitrone spin trap with a triphenyl phosphonium cation conjugated to the DEPMPO analogue. The Mito-DEPMPO-OOH adduct, formed from the trapping of superoxide by Mito-DEPMPO, was enzymatically generated using xanthine/xanthine oxidase and neuronal nitric oxide synthase, and chemically generated by KO2 in 18-crown-6. The Mito-DEPMPO-OOH adduct exhibits an eight-line EPR spectrum with partial asymmetry arising from the alternate line-width effect. The half-life of the Mito-DEPMPO-OOH adduct is 2-2.5-times greater than that of the DEPMPO-OOH. The Mito-DEPMPO-SG adduct, formed from the trapping of glutathiyl radicals by Mito-DEPMPO, is 3-times more persistent than the analogue DEPMPO-SG adduct. In this study, we describe the EPR characterization of spin adducts formed from Mito-DEPMPO. The EPR parameters of Mito-DEPMPO adducts are distinctly different and highly characteristic. The detection of superoxide from an intact mitochondrion was feasible with Mito-DEPMPO but not with DEPMPO. We conclude that Mito-DEPMPO nitrone and its analogues are more effective than most nitrone spin traps for trapping superoxide, hydroxyl, and thiyl radicals formed in biological systems, including mitochondria.",
author = "Mica{\"e}l Hardy and A. Rockenbauer and Jeannette V{\'a}squez-Vivar and Christopher Felix and Marcos Lopez and Satish Srinivasan and Narayan Avadhani and Paul Tordo and B. Kalyanaraman",
year = "2007",
month = "7",
doi = "10.1021/tx700101d",
language = "English",
volume = "20",
pages = "1053--1060",
journal = "Chemical Research in Toxicology",
issn = "0893-228X",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - Detection, characterization, and decay kinetics of ROS and thiyl adducts of mito-DEPMPO spin trap

AU - Hardy, Micaël

AU - Rockenbauer, A.

AU - Vásquez-Vivar, Jeannette

AU - Felix, Christopher

AU - Lopez, Marcos

AU - Srinivasan, Satish

AU - Avadhani, Narayan

AU - Tordo, Paul

AU - Kalyanaraman, B.

PY - 2007/7

Y1 - 2007/7

N2 - We report here the detection and characterization of spin adducts formed from the trapping of reactive oxygen species (superoxide and hydroxyl radicals) and glutathiyl and carbon-centered radicals by a newly synthesized nitrone, Mito-DEPMPO. This is a cationic nitrone spin trap with a triphenyl phosphonium cation conjugated to the DEPMPO analogue. The Mito-DEPMPO-OOH adduct, formed from the trapping of superoxide by Mito-DEPMPO, was enzymatically generated using xanthine/xanthine oxidase and neuronal nitric oxide synthase, and chemically generated by KO2 in 18-crown-6. The Mito-DEPMPO-OOH adduct exhibits an eight-line EPR spectrum with partial asymmetry arising from the alternate line-width effect. The half-life of the Mito-DEPMPO-OOH adduct is 2-2.5-times greater than that of the DEPMPO-OOH. The Mito-DEPMPO-SG adduct, formed from the trapping of glutathiyl radicals by Mito-DEPMPO, is 3-times more persistent than the analogue DEPMPO-SG adduct. In this study, we describe the EPR characterization of spin adducts formed from Mito-DEPMPO. The EPR parameters of Mito-DEPMPO adducts are distinctly different and highly characteristic. The detection of superoxide from an intact mitochondrion was feasible with Mito-DEPMPO but not with DEPMPO. We conclude that Mito-DEPMPO nitrone and its analogues are more effective than most nitrone spin traps for trapping superoxide, hydroxyl, and thiyl radicals formed in biological systems, including mitochondria.

AB - We report here the detection and characterization of spin adducts formed from the trapping of reactive oxygen species (superoxide and hydroxyl radicals) and glutathiyl and carbon-centered radicals by a newly synthesized nitrone, Mito-DEPMPO. This is a cationic nitrone spin trap with a triphenyl phosphonium cation conjugated to the DEPMPO analogue. The Mito-DEPMPO-OOH adduct, formed from the trapping of superoxide by Mito-DEPMPO, was enzymatically generated using xanthine/xanthine oxidase and neuronal nitric oxide synthase, and chemically generated by KO2 in 18-crown-6. The Mito-DEPMPO-OOH adduct exhibits an eight-line EPR spectrum with partial asymmetry arising from the alternate line-width effect. The half-life of the Mito-DEPMPO-OOH adduct is 2-2.5-times greater than that of the DEPMPO-OOH. The Mito-DEPMPO-SG adduct, formed from the trapping of glutathiyl radicals by Mito-DEPMPO, is 3-times more persistent than the analogue DEPMPO-SG adduct. In this study, we describe the EPR characterization of spin adducts formed from Mito-DEPMPO. The EPR parameters of Mito-DEPMPO adducts are distinctly different and highly characteristic. The detection of superoxide from an intact mitochondrion was feasible with Mito-DEPMPO but not with DEPMPO. We conclude that Mito-DEPMPO nitrone and its analogues are more effective than most nitrone spin traps for trapping superoxide, hydroxyl, and thiyl radicals formed in biological systems, including mitochondria.

UR - http://www.scopus.com/inward/record.url?scp=34547615931&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34547615931&partnerID=8YFLogxK

U2 - 10.1021/tx700101d

DO - 10.1021/tx700101d

M3 - Article

C2 - 17559235

AN - SCOPUS:34547615931

VL - 20

SP - 1053

EP - 1060

JO - Chemical Research in Toxicology

JF - Chemical Research in Toxicology

SN - 0893-228X

IS - 7

ER -