Peroxides in Biological Systems

Cadet, Jean; Mascio, Paolo Di

doi:10.1002/9780470682531.pat0357

Cited by 13 publications

(19 citation statements)

References 435 publications

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“…It has been proposed that . OH can promote the peroxidation of the polypeptide backbone as well as of the amino acid side-chains (37). Hydroxyl radical-mediated abstraction of the a-hydrogen atom of the polypeptide chain gives rise to a carbon-centred radical which subsequently reacts with oxygen to yield a peroxyl radical.…”

Section: Protein Hydroperoxidesmentioning

confidence: 99%

“…It has been reported that production of . OH close to DNA leads to the formation of 8-oxo-7,8-dihydro-2 0 -deoxyguanosine and other oxidation products, such as DNA hydroperoxides (37).…”

Section: Dna Hydroperoxidesmentioning

confidence: 99%

“…The main reaction of . OH with DNA involves addition to the carbon C5 and C6 of cytosine and thymine and to the C4, C5, and C8 of guanine and adenine (37). It has been shown that among nucleic acids, pyrimidine bases and in particular thymine was the preferential target for the radiation-induced formation of stable hydroperoxide at neutral and slightly acidic pH values (37).…”

Section: Dna Hydroperoxidesmentioning

confidence: 99%

“…OH with DNA involves addition to the carbon C5 and C6 of cytosine and thymine and to the C4, C5, and C8 of guanine and adenine (37). It has been shown that among nucleic acids, pyrimidine bases and in particular thymine was the preferential target for the radiation-induced formation of stable hydroperoxide at neutral and slightly acidic pH values (37). Later on, it was confirmed that exposure of naked nucleic acids to gamma rays, yielded a higher consumption of molecular oxygen for pyrimidine bases than for purine bases (37).…”

Section: Dna Hydroperoxidesmentioning

confidence: 99%

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Biological hydroperoxides and singlet molecular oxygen generation

et al. 2007

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Section: Protein Hydroperoxidesmentioning

confidence: 99%

“…It has been reported that production of . OH close to DNA leads to the formation of 8-oxo-7,8-dihydro-2 0 -deoxyguanosine and other oxidation products, such as DNA hydroperoxides (37).…”

Section: Dna Hydroperoxidesmentioning

confidence: 99%

Section: Dna Hydroperoxidesmentioning

confidence: 99%

Section: Dna Hydroperoxidesmentioning

confidence: 99%

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Biological hydroperoxides and singlet molecular oxygen generation

et al. 2007

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“…Luminol chemiluminescence is also applicable to an important group of substances, organic peroxy compounds (2)(3)(4)(5)(6), which have many important applications, such as free radical initiators, cross-linking agents and bleaching agents (7). They are also present in living organisms with connections to pathological effects and are possible contributors to some diseases, including arteriosclerosis, cancer and infections (8). The chemiluminescent assay of peroxy compounds is based upon the detection of light emitted during the catalystmediated oxidation of luminol.…”

Section: Introductionmentioning

confidence: 99%

The influence of dioxygen on luminol chemiluminescence

Baj¹,

Krawczyk²,

Staszewska³

2009

Luminescence

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Assays of peroxy compounds are commonly performed after chromatographic separation of analysed mixtures. In high-performance liquid chromatography (HPLC), solvent reservoirs are sparged by helium or inline vacuum-degassed in order to control the compressibility of the solvents for efficient pumping. In this study, we investigated the influence of degassing the reaction solution on the light output of the hemin-catalyzed luminol oxidation by various oxidants. We found that, when t-butyl hydroperoxide, hydrogen peroxide, n-butyl hydroperoxide, iodosobenzene and iodobenzene diacetate were used as oxidants, the luminol chemiluminescence was lowered by 50-70% compared with an equilibrated and degassed solution. The opposite effect was observed when dibenzoyl peroxide and 3-chloroperoxybenzoic acid were used as oxidants, as the chemiluminescence increased by approximately 20-30%. The reduced chemiluminescence was explained based on the known role of dioxygen in luminol chemiluminescence. The enhancement of chemiluminescence was rationalized by suggesting an alternative mechanism of luminol oxidation valid for peroxyacids and diacyl peroxides in which the reaction of a peroxyacid anion with the diazaquinone led to light emission with a higher quantum yield than the usual path, which is suppressed by the removal of dioxygen from the reaction solution.

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Singlet Molecular Oxygen Reactions with Nucleic Acids, Lipids, and Proteins

et al. 2019

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Singlet oxygen ( 1 O 2 ) is a biologically relevant reactive oxygen species capable of efficiently reacting with cellular constituents. The resulting oxidatively generated damage to nucleic acids, membrane unsaturated lipids, and protein components has been shown to be implicated in several diseases, including arthritis, cataracts, and skin cancer. Singlet oxygen may be endogenously produced, among various possibilities, by myeloperoxidase, an enzyme implicated in inflammation processes, and also efficiently in skin by the UVA component of solar radiation through photosensitization reactions. Emphasis is placed in this Review on the description of the main oxidation reactions initiated by 1 O 2 and the resulting modifications within key cellular targets, including guanine for nucleic acids, unsaturated lipids, and targeted amino acids. Most of these reactions give rise to peroxides and dioxetanes, whose formation has been rationalized in terms of [4+2] cycloaddition and 1,2-cycloaddition with dienes + olefins, respectively. The use of [ 18 O]-labeled thermolabile endoperoxides as a source of [ 18 O]-labeled 1 O 2 has been applied to study mechanistic aspects and preferential targets of 1 O 2 in biological systems. A relevant major topic deals with the search for the molecular signature of the 1 O 2 formation in targeted biomolecules within cells. It may be anticipated that [ 18 O]-labeled 1 O 2 and labeled peroxides in association with sensitive mass spectrometric methods should constitute powerful tools for this purpose.

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Peroxides in Biological Systems

Abstract: Introduction DNA Hydroperoxides Lipid Hydroperoxides Protein Hydroperoxides Cellular Indicators of Hydroperoxides Conclusions Acknowledgments

Cited by 13 publications

References 435 publications

Biological hydroperoxides and singlet molecular oxygen generation

Biological hydroperoxides and singlet molecular oxygen generation

The influence of dioxygen on luminol chemiluminescence

Singlet Molecular Oxygen Reactions with Nucleic Acids, Lipids, and Proteins

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