Metal specificity in DNA damage prevention by sulfur antioxidants

Battin, Erin E.; Brumaghim, Julia L.

doi:10.1016/j.jinorgbio.2008.06.010

Cited by 56 publications

(52 citation statements)

References 74 publications

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“…Collins et al have reported selenium-copper complexes that utilize both metal binding and ROS scavenging in oxidative stress prevention [28]. Our research has demonstrated that metal coordination is required for inhibition of copper-and ironmediated DNA damage by sulfur, oxo-sulfur, and selenium compounds [12,13,15,16]. Metal binding as a novel antioxidant mechanism for sulfur and selenium may be complementary to ROS scavenging and GPx activity.…”

Section: Introductionmentioning

confidence: 63%

“…or Fe 2? , and this observed antioxidant activity occurs at biological (low micromolar) concentrations by metal coordination [16], comparable to the levels of labile metal ion pools in cells [9,40,83,93]. Thus, the ability of sulfur-containing compounds to coordinate metals is extremely important in preventing the formation of ROS.…”

Section: Metal-binding Mechanisms For Sulfur Antioxidant Activitymentioning

confidence: 77%

“…Antioxidants, including polyphenols, sulfur-and seleniumcontaining compounds, enzymatic antioxidants such as superoxide dismutase (SOD) and glutathione peroxidase (GPx), and micronutrients such as vitamins C and E, have been extensively investigated, and numerous studies have demonstrated their antioxidant properties [1,[11][12][13][14][15][16][17][18][19]. For example, vitamin E supplements decrease the risk of colon and prostate cancers, and also reduce the risk of coronary disease by approximately 40% [20].…”

Section: Introductionmentioning

confidence: 99%

“…The protective effects of sulfur and selenium compounds against disease are commonly attributed to radical scavenging and enzymatic decomposition of oxygen metabolites [1,27]. More recently, coordination of sulfur and selenium compounds with metal ions has been proposed as an additional antioxidant mechanism [12,13,15,16]. Collins et al have reported selenium-copper complexes that utilize both metal binding and ROS scavenging in oxidative stress prevention [28].…”

Section: Introductionmentioning

confidence: 99%

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Antioxidant Activity of Sulfur and Selenium: A Review of Reactive Oxygen Species Scavenging, Glutathione Peroxidase, and Metal-Binding Antioxidant Mechanisms

Battin

Brumaghim

2009

Cell Biochem Biophys

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236

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It is well known that oxidation caused by reactive oxygen species (ROS) is a major cause of cellular damage and death and has been implicated in cancer, neurodegenerative, and cardiovascular diseases. Small-molecule antioxidants containing sulfur and selenium can ameliorate oxidative damage, and cells employ multiple antioxidant mechanisms to prevent this cellular damage. However, current research has focused mainly on clinical, epidemiological, and in vivo studies with little emphasis on the antioxidant mechanisms responsible for observed sulfur and selenium antioxidant activities. In addition, the antioxidant properties of sulfur compounds are commonly compared to selenium antioxidant properties; however, sulfur and selenium antioxidant activities can be quite distinct, with each utilizing different antioxidant mechanisms to prevent oxidative cellular damage. In the present review, we discuss the antioxidant activities of sulfur and selenium compounds, focusing on several antioxidant mechanisms, including ROS scavenging, glutathione peroxidase, and metal-binding antioxidant mechanisms. Findings of several recent clinical, epidemiological, and in vivo studies highlight the need for future studies that specifically focus on the chemical mechanisms of sulfur and selenium antioxidant behavior.

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Section: Introductionmentioning

confidence: 63%

Section: Metal-binding Mechanisms For Sulfur Antioxidant Activitymentioning

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antioxidant Activity of Sulfur and Selenium: A Review of Reactive Oxygen Species Scavenging, Glutathione Peroxidase, and Metal-Binding Antioxidant Mechanisms

Battin

Brumaghim

2009

Cell Biochem Biophys

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402

236

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“…The reduced and oxidized forms of glutathione also lowered Cu(I)-induced oxidative DNA damage through a mechanism that appears to involve Cu(I) binding. The S compound 3-carboxypropyl disulfide showed no antioxidant activity toward Cu(I)/H 2 O 2 oxidative damage; however, it did lower Fe(II)-mediated damage through a mechanism that appears to involve metal coordination (59). The S compounds methionine sulfoxide and methylcysteine sulfoxide also exhibited antioxidant activity toward the Cu(I)/H 2 O 2 system in a matter consistent with Cu coordination; however, in this case, it appears that metal coordination alone does not account for all of the antioxidant activity.…”

Section: Sulfur Compoundsmentioning

confidence: 92%

DNA-bound metal ions: recent developments

Morris

2014

Biomolecular Concepts

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Abstract:The affinity of metal ions for DNA is logical considering that the structure of DNA includes a phosphate backbone with a net-negative charge, a deoxyribose sugar with O atoms, and purine and pyrimidine bases that contain O and N atoms. DNA-metal ion interactions encompass a large area of research that ranges from the most fundamental characterization of DNA-metal ion binding to the role of DNA-bound metal ions in disease and human health. Alternative DNA base pairing mediated by metal binding is also being investigated and manipulated for applications in logic gates, molecular machines, and nanotechnology. This review highlights recent work aimed at understanding interactions of redox-active metal ions with DNA that provides a better understanding of the mechanisms by which various types of oxidative DNA damage (strand breakage and base modifications) occur. Antioxidants that mitigate oxidative DNA damage by coordinating metal ions that produce reactive oxygen species are addressed, as well as recent work on the effect of DNAmetal ion interactions and the efficacy of quinolone-based antibacterial drugs. Recent advances in metal-mediated base pairing that triggers conformational changes in DNA structure for use as selective metal ion sensors and novel nanotechnology applications are also included.

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Chemical repair of damaged leucine and tryptophane by thiophenols at close to diffusion‐controlled rates: Mechanisms and kinetics

et al. 2022

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Thiophenols are chemical species with multiple desirable biological properties, including their primary and secondary antioxidant capacity. In this work, the repairing antioxidant activity of eight different thiophenols has been investigated for damaged leucine and tryptophane. The investigation was carried out employing quantum mechanical and transition state methods to calculate the thermodynamic and kinetic data of the reactions involved, while simulating the biological conditions at physiological pH and aqueous and lipidic medium. The analysis of the atomic charges and the spin densities at each of the points on the potential energy surface was the tool that allowed the elucidation of the reaction mechanisms through which thiophenols repair the oxidative damage caused to the amino acids leucine and tryptophan. It was found that thiophenols can repair leucine via a hydrogen atom transfer mechanism in a manner which is similar to the one used by glutathione to repair the carbon-centered radicals of guanosine. In addition, thiophenols can also restore tryptophane, a nitrogen-centered radical, via proton-coupled electron transfer and single electron transfer mechanisms. Moreover, both processes occur at close to diffusion-controlled rates.

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Metal specificity in DNA damage prevention by sulfur antioxidants

Cited by 56 publications

References 74 publications

Antioxidant Activity of Sulfur and Selenium: A Review of Reactive Oxygen Species Scavenging, Glutathione Peroxidase, and Metal-Binding Antioxidant Mechanisms

Antioxidant Activity of Sulfur and Selenium: A Review of Reactive Oxygen Species Scavenging, Glutathione Peroxidase, and Metal-Binding Antioxidant Mechanisms

DNA-bound metal ions: recent developments

Chemical repair of damaged leucine and tryptophane by thiophenols at close to diffusion‐controlled rates: Mechanisms and kinetics

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