Correlating the GPx Activity of Selenocystine Derivatives with One-Electron Redox Reactions

Mishra, Beena; Barik, Atanu; Kunwar, Amit; Kumbhare, Liladhar B.; Priyadarsini, K. Indira; Jain, Vimal K.

doi:10.1080/10426500801901046

Cited by 20 publications

(14 citation statements)

References 7 publications

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“…Conversely, the lowest activity for 5 would be due to the ionization of the amino groups to NH 3 + , which should decrease the oxidizability of the selenium atom. [11] The order of the catalytic activity strongly suggested that the GPxlike activities of selenides in water can be controlled by the electronic effects from the terminal hydrophilic substituents as well as the steric environments around the selenium atom. Second, the catalytic activity of 1 was investigated by using a dithiol, that is, dithiothreitol (DTT red ), instead of a monothiol substrate.…”

Section: Resultsmentioning

confidence: 99%

A Water‐Soluble Cyclic Selenide with Enhanced Glutathione Peroxidase‐Like Catalytic Activities

Kumakura¹,

Mishra²,

et al. 2010

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Antioxidative catalytic activities of trans-3,4-dihydroxyselenolane (DHS red ), a water-soluble cyclic selenide, were investigated in the reaction of hydrogen peroxide with three different thiol substrates, monothiol glutathione (GSH), dithiol dithiothreitol (DTT red ), and polythiol reduced ribonuclease A (RNase A) having eight thiol groups along the polypeptide chain. For all the thiol substrates, DHS red exhibited higher glutathione peroxidase (GPx)-like antioxidative catalytic ac-

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Section: Resultsmentioning

confidence: 99%

A Water‐Soluble Cyclic Selenide with Enhanced Glutathione Peroxidase‐Like Catalytic Activities

Kumakura¹,

Mishra²,

et al. 2010

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“…5) [255]. The GPx activity of other selenocompounds without seleniumnitrogen bonds has also been investigated [202,256]. In one study, selenocystine and selenocystamine both had relatively similar GPx activity; however, 3,3-diselenobispropionic acid had GPx activity 25-29 times lower than [256].…”

Section: Glutathione Peroxidase Activity Of Selenium Compoundsmentioning

confidence: 98%

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

414

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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“…GPx activity measurement is a typical method used to determine selenium antioxidant activity, and a great deal of research has focused on the development of more potent GPx mimics, including small organoselenium compounds. [55][56][57][58][59][60] The selenium drug ebselen (2-phenyl-1,2-benzisoselazol-3(2H)-one) protects against ischemic brain injury in human clinical trials, 61 and prevents neurotoxicity in Parkinson's disease, a disease where ROS are considered the primary cause of pathogenesis. [61][62][63][64] The mechanism for this protective ability is thought to be reducing oxidative damage by H 2 O 2 in a manner similar to that of the GPx enzyme, and ebselen is typically used as the standard relative to which all selenium GPx measurements are compared.…”

Section: Glutathione Peroxidase Activity Of Selenium Compoundsmentioning

confidence: 99%

Preventing metal-mediated oxidative DNA damage with selenium compounds

et al. 2011

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Copper and iron are two widely studied transition metals associated with hydroxyl radical (˙OH) generation, oxidative damage, and disease development. Because antioxidants ameliorate metal-mediated DNA damage, DNA gel electrophoresis assays were used to quantify the ability of ten selenium-containing compounds to inhibit metal-mediated DNA damage by hydroxyl radical. In the Cu(I)/H(2)O(2) system, selenocystine, selenomethionine, and methyl-selenocysteine inhibit DNA damage with IC(50) values ranging from 3.34 to 25.1 μM. Four selenium compounds also prevent DNA damage from Fe(II) and H(2)O(2). Additional gel electrophoresis experiments indicate that Cu(I) or Fe(II) coordination is responsible for the selenium antioxidant activity. Mass spectrometry studies show that a 1 : 1 stoichiometry is the most common for iron and copper complexes of the tested compounds, even if no antioxidant activity is observed, suggesting that metal coordination is necessary but not sufficient for selenium antioxidant activity. A majority of the selenium compounds are electroactive, regardless of antioxidant activity, and the glutathione peroxidase activities of the selenium compounds show no correlation to DNA damage inhibition. Thus, metal binding is a primary mechanism of selenium antioxidant activity, and both the chemical functionality of the selenium compound and the metal ion generating damaging hydroxyl radical significantly affect selenium antioxidant behavior.

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Correlating the GPx Activity of Selenocystine Derivatives with One-Electron Redox Reactions

Cited by 20 publications

References 7 publications

A Water‐Soluble Cyclic Selenide with Enhanced Glutathione Peroxidase‐Like Catalytic Activities

A Water‐Soluble Cyclic Selenide with Enhanced Glutathione Peroxidase‐Like Catalytic Activities

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

Preventing metal-mediated oxidative DNA damage with selenium compounds

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