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Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review.

Macone A, Fontana M, Barba M, Botta B, Nardini M, Ghirga F, Calcaterra A, Pecci L, Matarese RM - Int J Mol Sci (2011)

Bottom Line: Attention has been focused on its antioxidant properties and on its reactivity against oxygen and nitrogen reactive species.All these studies report that aminoethylcysteine ketimine decarboxylated dimer is able to interact both with reactive oxygen and nitrogen species (hydrogen peroxide, superoxide anion, hydroxyl radical, peroxynitrite and its derivatives).Its antioxidant activity is similar to that of Vitamin E while higher than other hydrophilic antioxidants, such as trolox and N-acetylcysteine.

View Article: PubMed Central - PubMed

Affiliation: Department of Biochemical Sciences, Sapienza, University of Rome, Piazzale Aldo Moro 5, 00185, Rome, Italy; E-Mails: alberto.macone@uniroma1.it (A.M.); mario.fontana@uniroma1.it (M.F.); laura.pecci@uniroma1.it (L.P.).

ABSTRACT
Aminoethylcysteine ketimine decarboxylated dimer is a natural sulfur-containing compound detected in human plasma and urine, in mammalian brain and in many common edible vegetables. Over the past decade many studies have been undertaken to identify its metabolic role. Attention has been focused on its antioxidant properties and on its reactivity against oxygen and nitrogen reactive species. These properties have been studied in different model systems starting from plasma lipoproteins to specific cellular lines. All these studies report that aminoethylcysteine ketimine decarboxylated dimer is able to interact both with reactive oxygen and nitrogen species (hydrogen peroxide, superoxide anion, hydroxyl radical, peroxynitrite and its derivatives). Its antioxidant activity is similar to that of Vitamin E while higher than other hydrophilic antioxidants, such as trolox and N-acetylcysteine.

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Production of a dimeric form of aminoethylcysteine ketimine decarboxylated dimer in the presence of peroxynitrite. Reagents and conditions: (i) peroxynitrite.
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f4-ijms-12-03072: Production of a dimeric form of aminoethylcysteine ketimine decarboxylated dimer in the presence of peroxynitrite. Reagents and conditions: (i) peroxynitrite.

Mentions: Peroxynitrite is an endogenous mediator of various forms of tissue damage in several human pathologies, including neurodegenerative diseases, atherosclerosis, inflammatory and autoimmune diseases. [64,65]. Peroxynitrite is known to mediate oxidation of suitable substrates, either through a direct two-electron mechanism or through an indirect one-electron reaction involving hydroxyl (•OH) and nitrogen dioxide (•NO2) radicals released during peroxynitrite homolysis [59,66–68]. Under physiological conditions, peroxynitrite predominantly reacts with carbon dioxide [69] and the oxidative reactions of peroxynitrite are mediated by (i) the carbonate radical anion (CO3•−); (ii) •NO2 generated by decomposition of the short-lived peroxynitrite-CO2 adduct [70–72]. After reaction with peroxynitrite, 1 undergoes oxidative modifications, yielding a dimeric form of the parent compound (6) (Scheme 3), which has so far been isolated and characterized using 1D and 2D nuclear magnetic resonanceand ion trap mass spectrometry [39]. The proposed mechanism for the formation of the peroxynitrite-oxidation derivative of 1 involves the radical dimerization of 1 [39].


Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review.

Macone A, Fontana M, Barba M, Botta B, Nardini M, Ghirga F, Calcaterra A, Pecci L, Matarese RM - Int J Mol Sci (2011)

Production of a dimeric form of aminoethylcysteine ketimine decarboxylated dimer in the presence of peroxynitrite. Reagents and conditions: (i) peroxynitrite.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3116176&req=5

f4-ijms-12-03072: Production of a dimeric form of aminoethylcysteine ketimine decarboxylated dimer in the presence of peroxynitrite. Reagents and conditions: (i) peroxynitrite.
Mentions: Peroxynitrite is an endogenous mediator of various forms of tissue damage in several human pathologies, including neurodegenerative diseases, atherosclerosis, inflammatory and autoimmune diseases. [64,65]. Peroxynitrite is known to mediate oxidation of suitable substrates, either through a direct two-electron mechanism or through an indirect one-electron reaction involving hydroxyl (•OH) and nitrogen dioxide (•NO2) radicals released during peroxynitrite homolysis [59,66–68]. Under physiological conditions, peroxynitrite predominantly reacts with carbon dioxide [69] and the oxidative reactions of peroxynitrite are mediated by (i) the carbonate radical anion (CO3•−); (ii) •NO2 generated by decomposition of the short-lived peroxynitrite-CO2 adduct [70–72]. After reaction with peroxynitrite, 1 undergoes oxidative modifications, yielding a dimeric form of the parent compound (6) (Scheme 3), which has so far been isolated and characterized using 1D and 2D nuclear magnetic resonanceand ion trap mass spectrometry [39]. The proposed mechanism for the formation of the peroxynitrite-oxidation derivative of 1 involves the radical dimerization of 1 [39].

Bottom Line: Attention has been focused on its antioxidant properties and on its reactivity against oxygen and nitrogen reactive species.All these studies report that aminoethylcysteine ketimine decarboxylated dimer is able to interact both with reactive oxygen and nitrogen species (hydrogen peroxide, superoxide anion, hydroxyl radical, peroxynitrite and its derivatives).Its antioxidant activity is similar to that of Vitamin E while higher than other hydrophilic antioxidants, such as trolox and N-acetylcysteine.

View Article: PubMed Central - PubMed

Affiliation: Department of Biochemical Sciences, Sapienza, University of Rome, Piazzale Aldo Moro 5, 00185, Rome, Italy; E-Mails: alberto.macone@uniroma1.it (A.M.); mario.fontana@uniroma1.it (M.F.); laura.pecci@uniroma1.it (L.P.).

ABSTRACT
Aminoethylcysteine ketimine decarboxylated dimer is a natural sulfur-containing compound detected in human plasma and urine, in mammalian brain and in many common edible vegetables. Over the past decade many studies have been undertaken to identify its metabolic role. Attention has been focused on its antioxidant properties and on its reactivity against oxygen and nitrogen reactive species. These properties have been studied in different model systems starting from plasma lipoproteins to specific cellular lines. All these studies report that aminoethylcysteine ketimine decarboxylated dimer is able to interact both with reactive oxygen and nitrogen species (hydrogen peroxide, superoxide anion, hydroxyl radical, peroxynitrite and its derivatives). Its antioxidant activity is similar to that of Vitamin E while higher than other hydrophilic antioxidants, such as trolox and N-acetylcysteine.

Show MeSH