Mechanisms by which cysteine can inhibit or promote the oxidation of low density lipoprotein by copper

Patterson, Rebecca A.; Lamb, David; Leake, David S.

doi:10.1016/s0021-9150(03)00154-0

Cited by 25 publications

(9 citation statements)

References 44 publications

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“…The highest ESR intensity was observed 1 min after addition of H 2 O 2 indicating rapid formation of hydroxyl radical. This observation is consistent with that of Patterson et al 65 . These investigators found that within 2 min after mixing Cu 2+ (10 μM) and cysteine (100 μM), approximately 75% of Cu 2+ is reduced to Cu + followed by minimal reduction thereafter.…”

Section: Resultssupporting

confidence: 94%

Dual Role of Selected Antioxidants Found in Dietary Supplements: Crossover between Anti- and Pro-Oxidant Activities in the Presence of Copper

Yin

Lutterodt

et al. 2012

J. Agric. Food Chem.

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Overproduction of reactive oxygen species (ROS) in vivo can result in damage associated with many aging-associated diseases. Defenses against ROS that have evolved include antioxidant enzymes, such as superoxide dismutases, peroxidases, and catalases, which can scavenge ROS. In addition, endogenous and dietary antioxidants play an important role in moderating damage associated with ROS. In this study, we use four common dietary antioxidants to demonstrate that, in the presence of copper (cupric sulfate and cupric gluconate) and physiologically relevant levels of hydrogen peroxide, these antioxidants can also act as pro-oxidants by producing hydroxyl radicals. Using electron spin resonance (ESR) spin trapping techniques, we demonstrate that the level of hydroxyl radical formation is a function of the pH of the medium and the relative amounts of antioxidant and copper. Based on the level of hydroxyl radical formation, the relative pro-oxidant potential of these antioxidants is: cysteine > ascorbate >EGCG > GSH. It has been reported that copper sequestered by protein ligands, as happens in vivo, loses its redox activity (diminishing/abolishing the formation of free radicals). However, in the presence of hydrogen peroxide, cysteine and GSH efficiently react with cupric sulfate sequestered with bovine serum albumin to generate hydroxyl radicals. Overall, the results demonstrate that, in the presence of copper endogenous and dietary antioxidants can also exhibit pro-oxidative activity.

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Section: Resultssupporting

confidence: 94%

Dual Role of Selected Antioxidants Found in Dietary Supplements: Crossover between Anti- and Pro-Oxidant Activities in the Presence of Copper

Yin

Lutterodt

et al. 2012

J. Agric. Food Chem.

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“…Physiologically, the action of lipid peroxidation has been investigated, as this leads to atherosclerosis (26). Lipids are subject to peroxidation by sulfur dioxide and copper ions, which may act as a catalyst (27,28). It is possible that a mechanism exists whereby atmospheric light (29) or sulfur dioxide interacts with the lipid fraction of parchment, causing its peroxidation and subsequent generation of reactive oxygen species with the capacity to damage the collagen structure of parchment.…”

Section: Discussionmentioning

confidence: 99%

Evidence of a distinct lipid fraction in historical parchments: a potential role in degradation?

Ghioni

Kennedy

Aliev

et al. 2005

Journal of Lipid Research

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Parchment, a biologically based material obtained from the processed hides of animals such as cattle and sheep, has been used for millennia as a writing medium. Although numerous studies have concentrated on the structure and degradation of collagen within parchment, little attention has been paid to noncollagenous components, such as lipids. In this study, we present the results of biochemical and structural analyses of historical and newly manufactured parchment to examine the potential role that lipid plays in parchment stability. The lipid fraction extracted from the parchments displayed different fatty acid compositions between historical and reference materials. Gas chromatography, small-angle X-ray scattering, and solid-state NMR were used to identify and investigate the lipid fraction from parchment samples and to study its contribution to collagen structure and degradation. We hypothesize that the origin of this lipid fraction is either intrinsic, attributable to incomplete fat removal in the manufacturing process, or extrinsic, attributable to microbiological attack on the proteinaceous component of parchments. Furthermore, we consider that the possible formation of protein-lipid complexes in parchment over the course of oxidative degradation may be mediated by reactive oxygen species formed by lipid peroxidation. Parchment is a material of biological origin that has been used for centuries as a foundation for historical documents and works of art, including most of the written history of Europe. Consequently, the conservation of parchment has frequently been a foremost concern. Many early methods of intervention did more harm than good to the original documents, and the work of modern conservators is often made more difficult because they have to not only preserve the historical material but also undo earlier treatments or cope with the damage caused by overzealous washing, flattening, or other methods applied in the past (1).Some recent work has focused on the protein structure of parchment and changes to the material on the molecular level over time. Parchment, primarily originating from the hides of cattle, sheep, and goats, is predominantly composed of type I collagen, along with some associated macromolecules such as proteoglycans (2). The hierarchical structure of collagen in a feltwork, which provided mechanical strength to the skin of the animal when it was alive, is now responsible for maintaining the parchment as a viable storage medium. As the collagen degrades over time, the parchment loses strength, becomes brittle, and deteriorates to the point that it can no longer be used. The basis for the biodegradation of collagen within parchment is largely unresolved and is the focus of several current and past research programs, which intend to minimize the loss of cultural and historical artifacts resulting from the biodegradation of collagen in parchment (3)(4)(5).The presence of a lipid fraction in parchment has not been examined extensively, nor has the role that lipids may play in t...

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“…Cysteine (Cys) exhibits chemical properties similar to homocysteine through its sulfhydryl (–SH) group, and its levels in plasma are 20-fold higher than homocysteine [4]. However, its potential noxious effects in cardiovascular disease have till now received little attention [5–7].…”

Section: Introductionmentioning

confidence: 99%

Plasma Total Cysteine and Cardiovascular Risk Burden: Action and Interaction

Chiara

Sedda

Parolini

et al. 2012

The Scientific World Journal

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We hypothesized that redox analysis could provide sensitive markers of the oxidative pathway associated to the presence of an increasing number of cardiovascular risk factors (RFs), independently of type. We classified 304 subjects without cardiovascular disease into 4 groups according to the total number of RFs (smoking, hypertension, hypercholesterolaemia, hyperhomocysteinaemia, diabetes, obesity, and their combination). Oxidative stress was evaluated by measuring plasma total and reduced homocysteine, cysteine (Cys), glutathione, cysteinylglycine, blood reduced glutathione, and malondialdehyde. Twenty-seven percent of subjects were in group 0 RF, 26% in 1 RF, 31% in 2 RF, and 16% in ≥3 RF. By multivariable ordinal regression analysis, plasma total Cys was associated to a higher number of RF (OR = 1.068; 95% CI = 1.027–1.110, P = 0.002). Total RF burden is associated with increased total Cys levels. These findings support a prooxidant effect of Cys in conjunction with RF burden, and shed light on the pathophysiologic role of redox state unbalance in preclinical atherosclerosis.

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Mechanisms by which cysteine can inhibit or promote the oxidation of low density lipoprotein by copper

Cited by 25 publications

References 44 publications

Dual Role of Selected Antioxidants Found in Dietary Supplements: Crossover between Anti- and Pro-Oxidant Activities in the Presence of Copper

Dual Role of Selected Antioxidants Found in Dietary Supplements: Crossover between Anti- and Pro-Oxidant Activities in the Presence of Copper

Evidence of a distinct lipid fraction in historical parchments: a potential role in degradation?

Plasma Total Cysteine and Cardiovascular Risk Burden: Action and Interaction

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