Oxygen-Centered Spin Adducts of 5,5-Dimethyl-1-pyrrolineN-oxide (DMPO) and 2H-Imidazole 1-Oxides

Krainev, Arkadi G.; Williams, Todd D.; Bigelow, Diana J.

doi:10.1006/jmrb.1996.0093

Cited by 31 publications

(22 citation statements)

References 3 publications

(4 reference statements)

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“…Mass spectrometry (MS) has been shown to be a suitable tool to identify and verify spin adducts. these techniques were applied to the characterization of radical adducts of the nitrones benzylidene(tert-butyl)azane oxide (PBN) 15,16 , 4-{[tertbutyl(oxido)imino]-methyl} pyridine 1-oxide (PoBN), [17][18][19][20] 2,2 dimethyl-3,4-dihydropyrroline N-oxide (DMPo), [21][22][23][24][25][26][27] N-arylc,c-dimethoxycarbonylnitrones 28 and (2-methyl-1-oxido-3,4-dihydro-2H-pyrrol-2-yl) phosphonate (DEPMPo). 29 the mass spectrometric analyses were performed on the isolated radical spin adducts using high-performance liquid chromatography (HPLc) or with on-line chromatographic system such as HPLc or Gc.…”

Section: Europeanmentioning

confidence: 99%

“…29 the mass spectrometric analyses were performed on the isolated radical spin adducts using high-performance liquid chromatography (HPLc) or with on-line chromatographic system such as HPLc or Gc. [15][16][17][18][19][20][21] recently, the structural determination of free radical spin adducts from a complex mixture has been reported without any preliminary separation. [22][23][24][25][26][27][28][29] Each method presents different advantages and disadvantages.…”

Section: Europeanmentioning

confidence: 99%

“…However, systems such as Gc-MS are easily available and the hydroxylamine or nitrones obtained by oxido-reductive processes have been shown to be readily detected. [15][16][17][18][19][20][21] recently, a novel nitrone spin trap containing a phosphorous atom, namely 5-diisopropoxyphosphoryl-5-methyl-1-pyrroline-N-oxide (DIPPMPo) was investigated. 30 figure 1 shows the DIPPMPo spin trap system and its operational chemistry.…”

Section: Europeanmentioning

confidence: 99%

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Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and ³¹P Nuclear Magnetic Resonance

Zoia

Argyropoulos

2010

Eur J Mass Spectrom (Chichester)

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All rights reserved EuroPEAN JourNAL of MASS SPEctroMEtry for many years, spin traps have been used to decrease the reactivity of free radicals in order for them to be identified and detected by electron paramagnetic resonance (EPr) spectrometry, thereby allowing the acquisition of abundant information on the production of such species in biological, biochemical and chemical systems. [1][2][3][4] During this technique, a highly reactive free radical typically reacts with a double bond of a diamagnetic compound (the spin trap) to form a more stable radical (the spin adduct) which can be detected by EPr spectrometry. [5][6][7][8][9] Nitrones are the most frequently used compounds as spin trapping agents, and the spin adducts being, in this case, a nitroxide. recent accounts 10 have demonstrated that phosphorus-containing spin traps give rise to radical adducts that have longer half-lives compared Characterization of free radical spin adducts of 5-diisopropyloxy-phosphoryl-5-methyl-1-pyrroline-N-oxide using mass spectrometry and 31 P nuclear magnetic resonance 5-Diisopropyloxy-phosphoryl-5-methyl-1-pyrroline-N-oxide (DIPPMPO) was used to trap a variety of free radicals and the stable compounds generated by the natural decomposition of the initially formed spin adducts were characterized by 31 P nuclear magnetic resonance (NMR) and mass spectrometry. Initially, the starting spin trap DIPPMPO was completely characterized using GC-MS and its fragmentation pathway was studied in detail. Then, DIPPMPO was used to trap an oxygen-centered free radical (the hydroxyl radical • OH) and two carbon-centered free radicals (methyl • CH 3 and 1-phenyl-ethanol-1-yl • CCH 3 (OH)Ph radicals). The 31 P NMR signals were thus assigned and the structures of adducts were studied and confirmed by mass spectrometry. Overall, the fragmentation pathways of the radical adducts proceed mainly via the loss of the diisopropyloxy(oxido)phosphoranyl radical. For the specific case of trapping•OH radicals, it is possible to visualize the rearrangement of the nitroxide radical adduct to its nitrone form as invoked in the literature. This spin trapping technique, coupled with 31 P NMR and MS, provides a tool for the identification of short-lived and low molecular weight free radicals present in a variety of processes.

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Section: Europeanmentioning

confidence: 99%

Section: Europeanmentioning

confidence: 99%

Section: Europeanmentioning

confidence: 99%

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Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and ³¹P Nuclear Magnetic Resonance

Zoia

Argyropoulos

2010

Eur J Mass Spectrom (Chichester)

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“…In one experiment, LDL oxidation was initiated by the water-soluble azoinitiator, 2,2 -azobis-[2-amidinopropane] dihydrochloride (AAPH), which generates alkylperoxyl radicals directly by temperature-dependent unimolecular decomposition within the aqueous phase (Rice-Evans et al 1996). The peroxyl radicals are rapidly decomposed to alkoxyl radicals (Krainev et al 1996). In another experiment, we used 1,1-diphenyl-2-picrylhydrazyl (DPPH), a stable, lipidsoluble free radical that exhibits a strong absorption at 516 nm that is reduced when DPPH reacts with a free radical scavenger (Blois 1958).…”

Section: Introductionmentioning

confidence: 99%

In vitro free radical scavenging capacity of thyroid hormones and structural analogues

Oziol¹,

Fauré²,

Vergely³

et al. 2001

Journal of Endocrinology

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It was reported that thyroid hormones decreased Cu 2+ -induced low-density lipoprotein (LDL) oxidation in vitro. Here, we investigated free radical scavenging capacities of thyroid hormones (3,5,3 -tri-iodo-L-thyronine (T 3 ), thryoxine (T 4 ) and 3,3 ,5 -tri-iodo-L-thyronine (rT 3 )) and structural analogues (L-thryonine (T 0 ), 3,5,3 -tri-iodothyroacetic acid (TA 3 ) and 3,5,3 ,5 -tetraiodothyroacetic acid (TA 4 )), using three different models of free radical generation. T 0 , T 3 and TA 3 slowed down production of conjugated diene and thiobarbituric acidreactive substances during LDL oxidation by 2,2 -azobis-[2-amidinopropane] (water-soluble), whereas rT 3 , T 4 and TA 4 had practically no effect. In this system, T 0 was the more active compound. Using a 1,1-diphenyl-2-picrylhydrazyl (lipid-soluble) test, all compounds also revealed free radical scavenging capacities, but rT 3 , T 4 and TA 4 were more active than T 0 , T 3 and TA 3 . T 3 was able to scavenge superoxide anion and hydroxyl radicals generated in an aqueous phase by a xanthine-xanthine oxidase system, as measured by electron paramagnetic resonance spectroscopy. It may be concluded that: (1) thyroid hormones and analogues with a 4 -hydroxy diphenylether structure have free radical scavenging capacities, (2) this property is influenced by the number of iodines on the phenolic ring, and (3) thyroid hormone scavenging capacity should not be the only mechanism explaining their protective effect on Cu 2+ -induced LDL oxidation. The physiological significance of the findings is discussed.

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“…For example, the thermolabile water-soluble azo initiator 2,2' azobis (2-amidinopropane) dihydrochloride (AAPH) has been utilized in order to expose SR membranes to peroxyl and alkoxyl radicals, which are common cellular ROS (152,(170)(171)(172). Exposure of SR to AAPH results in a dose-dependent inactivation of the CaATPase and a pattern of oxidation that is similar to that from another oxidant, H 2 O 2 , but quite distinct from that of aging, particularly with respect to the bityrosine crosslinking resulting from in vitro oxidation.…”

Section: By Water-soluble and Lipid Soluble Radicalsmentioning

confidence: 99%

Protein oxidation and age-dependent alterations in calcium homeostasis

Squier¹

2000

Front Biosci

102

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Oxygen-Centered Spin Adducts of 5,5-Dimethyl-1-pyrrolineN-oxide (DMPO) and 2H-Imidazole 1-Oxides

Cited by 31 publications

References 3 publications

Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and ³¹P Nuclear Magnetic Resonance

Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and ³¹P Nuclear Magnetic Resonance

In vitro free radical scavenging capacity of thyroid hormones and structural analogues

Protein oxidation and age-dependent alterations in calcium homeostasis

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Oxygen-Centered Spin Adducts of 5,5-Dimethyl-1-pyrrolineN-oxide (DMPO) and 2H-Imidazole 1-Oxides

Cited by 31 publications

References 3 publications

Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and 31P Nuclear Magnetic Resonance

Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and 31P Nuclear Magnetic Resonance

In vitro free radical scavenging capacity of thyroid hormones and structural analogues

Protein oxidation and age-dependent alterations in calcium homeostasis

Contact Info

Product

Resources

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Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and ³¹P Nuclear Magnetic Resonance

Characterization of Free Radical Spin Adducts of 5-Diisopropyloxy-Phosphoryl-5-Methyl-1-Pyrroline-N-Oxide Using Mass Spectrometry and ³¹P Nuclear Magnetic Resonance