The formation of malonaldehyde in irradiated carbohydrates

Bucknall, Terrence; Edwards, Haydn E.; Kemsley, Kenneth G.; Moore, J.S.; Phillips, Glyn O.

doi:10.1016/s0008-6215(00)83377-7

Cited by 45 publications

(19 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the studies reported in the present paper, deoxyribose and benzoate were used to detect damage by OH in the presence and in the absence of EDTA. Damage to the carbohydrate deoxyribose by a hydrogenabstraction mechanism results in the release of thiobarbituric acid-reactive material (Bucknall et al, 1978;Von Sonntag, 1980; Gutteridge, 1981), whereas benzoate is hydroxylated to hydroxybenzoates by an addition reaction (Armstrong et al, 1960) as well as decarboxylated to phenol (Loeff & Swallow, 1964;Winston & Cederbaum, 1982). By using the hydrogenabstraction and addition reactions it was found that in most cases EDTA increased the effectiveness of the OH' scavengers.…”

Section: Introductionmentioning

confidence: 99%

Ferrous-salt-promoted damage to deoxyribose and benzoate. The increased effectiveness of hydroxyl-radical scavengers in the presence of EDTA

Gutteridge

1987

Biochemical Journal

257

110

View full text Add to dashboard Cite

Hydroxyl radicals (OH.) in free solution react with scavengers at rates predictable from their known second-order rate constants. However, when OH. radicals are produced in biological systems by metal-ion-dependent Fenton-type reactions scavengers do not always appear to conform to these established rate constants. The detector molecules deoxyribose and benzoate were used to study damage by OH. involving a hydrogen-abstraction reaction and an aromatic hydroxylation. In the presence of EDTA the rate constant for the reaction of scavengers with OH. was generally higher than in the absence of EDTA. This radiomimetic effect of EDTA can be explained by the removal of iron from the detector molecule, where it brings about a site-specific reaction, by EDTA allowing more OH. radicals to escape into free solution to react with added scavengers. The deoxyribose assay, although chemically complex, in the presence of EDTA appears to give a simple and cheap method of obtaining rate constants for OH. reactions that compare well with those obtained by using pulse radiolysis.

show abstract

Section: Introductionmentioning

confidence: 99%

Ferrous-salt-promoted damage to deoxyribose and benzoate. The increased effectiveness of hydroxyl-radical scavengers in the presence of EDTA

Gutteridge

1987

Biochemical Journal

257

110

View full text Add to dashboard Cite

show abstract

“…The ubiquitous natural compound malondialdehyde (MDA) is produced in substantial quantity in mammalian tissues both as an end product of unsaturated lipid peroxidation and as a side product of prostaglandin and thromboxane biosynthesis (1)(2)(3)(4). It also is produced in the "/-irradiation of carbohydrates (5). The measurement of MDA by the thiobarbituric acid test has been used commonly as a method for the detection of peroxidation of unsaturated fatty acids and in the estimation of oxidative rancidity in foods (2,3,6).…”

mentioning

confidence: 99%

The chemistry of lipid peroxidation metabolites: Crosslinking reactions of malondialdehyde

Nair

Cooper

Vietti

et al. 1986

Lipids

138

View full text Add to dashboard Cite

Malondialdehyde reacts readily with amino acids to form adducts containing vinylogous amidine linkages. Crosslinking reactions between nucleic acid bases and amino acids induced by malondialdehyde also have been investigated. The physical data obtained for the adducts provide structural information on the possible mode of crosslinking of proteins and nucleic acids induced by this lipid metabolite.

show abstract

“…A thiobarbituric acid (TBA) assay for hydroxyl radical (OH•) detection was used that is based upon the detection of hydroxyl radical attack on, and degradation of, the sugar deoxyribose (2-deoxy-D-ribose) [2] , [3] , [12] , [13] , [15] – [17] , [19] , [20] , [26] – [39] . When the resulting degradation product is heated under acidic conditions, malondialdehyde (MDA) is formed and that is detected by its ability to react with thiobarbituric acid (TBA) to form a pink chromogen.…”

Section: Methodsmentioning

confidence: 99%

Changes in Dry State Hemoglobin over Time Do Not Increase the Potential for Oxidative DNA Damage in Dried Blood

Marrone

Ballantyne

2009

PLoS ONE

View full text Add to dashboard Cite

BackgroundHemoglobin (Hb) is the iron-containing oxygen transport protein present in the red blood cells of vertebrates. Ancient DNA and forensic scientists are particularly interested in Hb reactions in the dry state because both regularly encounter aged, dried bloodstains. The DNA in such stains may be oxidatively damaged and, in theory, may be deteriorated by the presence of Hb. To understand the nature of the oxidative systems potentially available to degrade DNA in the presence of dried Hb, we need to determine what molecular species Hb forms over time. These species will determine what type of iron (i.e. Fe2+/Fe3+/Fe4+) is available to participate in further chemical reactions. The availability of “free” iron will affect the ability of the system to undergo Fenton-type reactions which generate the highly reactive hydroxyl radical (OH•). The OH• can directly damage DNA.Methodology/Principal FindingsOxygenated Hb (oxyHb) converts over time to oxidized Hb (metHb), but this happens more quickly in the dry state than in the hydrated state, as shown by monitoring stabilized oxyHb. In addition, dry state oxyHb converts into at least one other unknown species other than metHb. Although “free” iron was detectable as both Fe2+ and Fe3+ in dry and hydrated oxyHb and metHb, the amount of ions detected did not increase over time. There was no evidence that Hb becomes more prone to generating OH• as it ages in either the hydrated or dry states.ConclusionsThe Hb molecule in the dried state undergoes oxidative changes and releases reactive Fe(II) cations. These changes, however, do not appear to increase the ability of Hb to act as a more aggressive Fenton reagent over time. Nevertheless, the presence of Hb in the vicinity of DNA in dried bloodstains creates the opportunity for OH•-induced oxidative damage to the deoxyribose sugar and the DNA nucleobases.

show abstract

The formation of malonaldehyde in irradiated carbohydrates

Cited by 45 publications

References 20 publications

Ferrous-salt-promoted damage to deoxyribose and benzoate. The increased effectiveness of hydroxyl-radical scavengers in the presence of EDTA

Ferrous-salt-promoted damage to deoxyribose and benzoate. The increased effectiveness of hydroxyl-radical scavengers in the presence of EDTA

The chemistry of lipid peroxidation metabolites: Crosslinking reactions of malondialdehyde

Changes in Dry State Hemoglobin over Time Do Not Increase the Potential for Oxidative DNA Damage in Dried Blood

Contact Info

Product

Resources

About