Synthesis of telluroamino acid derivatives with remarkable GPx like activity

Braga, Antônio L.; Alberto, Eduardo E.; Soares, Letiére C.; Rocha, João Batista Teixeira da; Sudati, Jéssie Haigert; Roos, Daniel Henrique

doi:10.1039/b814990a

Cited by 55 publications

(26 citation statements)

References 34 publications

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“…[13] Although the telluro analogues showed high catalytic activity (T 50 about 2 min), the selenide ones were not able to promote the reduction of H 2 O 2 at an appreciable rate. Encouraged by the Table 1.…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenium with Pronounced GPx‐Like Activity

et al. 2009

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New chiral selenide‐ and diselenide amino acid derivatives have been synthesized. By a simple and efficient two‐step route, these new compounds were obtained from inexpensive and commercially available L‐amino acids. The products, with a highly modular character, were obtained in good to excellent yields. Selected examples were also efficiently used as GPx mimics, catalyzing the reduction of H2O2 to water at the expense of PhSH. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenium with Pronounced GPx‐Like Activity

et al. 2009

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“…Thus increased activities of SOD and CAT may serve as protective responses to eliminate reactive free radicals [49]. GPx is involved in catalyzing the reduction of H 2 O 2 at the expense of reduced GSH [50]. The level of GPx in the DCA-intoxicated rats, namely those receiving the higher dose, was depleted which can be attributed to either increased H 2 O 2 generation or decreased GSH concentration.…”

Section: Discussionmentioning

confidence: 99%

Dichloroacetic acid-induced testicular toxicity in male rats and the protective effect of date fruit extract

Arem

Lahouar

Saafi

et al. 2017

BMC Pharmacol Toxicol

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BackgroundThe present study was designed to investigate the protective effect of aqueous date extract (ADE) against the dichloroacetic acid (DCA)-induced testicular injury in rats.MethodsForty-eight male Wistar rats were randomly divided into six groups of eight: group I served as the control; group II was given ADE (4 ml/kg) by gavage; groups III and IV received DCA at 0.5 and 2 g/L drinking water, respectively; and groups V and VI received DCA at 0.5 and 2 g/L drinking water, respectively, before ADE administration. The experiment was performed for two months.ResultsResults showed that the absolute weights of testes and epididymis were decreased following the DCA administration. The testosterone, FSH and LH levels were also decreased. Severe histopathological changes in testes were observed including degeneration of seminiferous tubules and depletion of germ cells. These changes were associated with alterations of oxidative stress markers. Levels of lipid peroxidation and SOD and CAT activities were increased, while activity of GPx and GSH levels were decreased. Pretreatment with ADE has effectively alleviated the oxidative stress induced by DCA thereby restoring these parameters to normal values.ConclusionsThese results suggest that ADE has a protective effect over DCA-induced oxidative damage in rat testes.

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“…This compound was synthesized by the method previously described by Braga et al (2009). TeAsp solutions were prepared in dimethyl sulfoxide (DMSO).…”

Section: Methodsmentioning

confidence: 99%

“…The compound studied on the present work, (S )-dimethyl 2-(3-(phenyltellanyl) propanamido) succinate (TeAsp), is a new telluroamino acid derivative of aspartic acid that was found to be the most potent mimetic of GPx among 20 newly synthesized derivatives (Braga et al 2009; Alberto et al 2009) presenting antioxidant properties in vitro . However, when administered to rodents this compound showed potent genotoxic and mutagenic actions (Meinerz et al 2011).…”

Section: Introductionmentioning

confidence: 99%

Sub-acute administration of (S)-dimethyl 2-(3-(phenyltellanyl) propanamido) succinate induces toxicity and oxidative stress in mice: unexpected effects of N-acetylcysteine

et al. 2013

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The organic tellurium compound (S)-dimethyl 2-(3-(phenyltellanyl) propanamide) succinate (TeAsp) exhibits thiol-peroxidase activity that could potentially offer protection against oxidative stress. However, data from the literature show that tellurium is a toxic agent to rodents. In order to mitigate such toxicity, N-acetylcysteine (NAC) was administered in parallel with TeAsp during 10 days. Mice were separated into four groups receiving daily injections of (A) vehicle (PBS 2.5 ml/kg, i.p. and DMSO 1 ml/kg, s.c.), (B) NAC (100 mg/kg, i.p. and DMSO s.c.), (C) PBS i.p. and TeAsp (92.5 μmol/kg, s.c), or (D) NAC plus TeAsp. TeAsp treatment started on the fourth day. Vehicle or NAC-treated animals showed an increase in body weight whereas TeAsp caused a significant reduction. Contrary to expected, NAC co-administration potentiated the toxic effect of TeAsp, causing a decrease in body weight. Vehicle, NAC or TeAsp did not affect the exploratory and motor activity in the open-field test at the end of the treatment, while the combination of NAC and TeAsp produced a significant decrease in these parameters. No DNA damage or alterations in cell viability were observed in leukocytes of treated animals. Treatments produced no or minor effects on the activities of antioxidant enzymes catalase, glutathione peroxidase and glutathione reductase, whereas the activity of the thioredoxin reductase was decreased in the brain and increased the liver of the animals in the groups receiving TeAsp or TeAsp plus NAC. In conclusion, the toxicity of TeAsp was potentiated by NAC and oxidative stress appears to play a central role in this process.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-182) contains supplementary material, which is available to authorized users.

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Synthesis of telluroamino acid derivatives with remarkable GPx like activity

Abstract: A series of modular telluroamino acid derivatives with remarkable GPx-like behavior was prepared in an efficient and short two-step synthesis.

Cited by 55 publications

References 34 publications

Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenium with Pronounced GPx‐Like Activity

Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenium with Pronounced GPx‐Like Activity

Dichloroacetic acid-induced testicular toxicity in male rats and the protective effect of date fruit extract

Sub-acute administration of (S)-dimethyl 2-(3-(phenyltellanyl) propanamido) succinate induces toxicity and oxidative stress in mice: unexpected effects of N-acetylcysteine

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