Organoselenium and Organotellurium Compounds:  Toxicology and Pharmacology

Nogueira, Cristina W.; Zeni, Gilson; Rocha, João Batista Teixeira da

doi:10.1021/cr0406559

Cited by 1,658 publications

(697 citation statements)

References 380 publications

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“…6,[10][11][12] We have demonstrated that the inhibition of mammalian δ-ALA-D by diphenyl diselenide was dependent on the oxidation of cysteinyl residues located in the active site of the enzyme and that in an anaerobic environment the oxidation and inhibition of δ-ALA-D by diphenyl diselenide was markedly decreased. 10,12 These results support the view that the catalytic oxidation of thiols by diphenyl diselenide (and analogs) depends on the instability of the selenol-selenolate in an aerobic environment, i.e., molecular oxygen can oxidized back the selenol groups to a diselenide.…”

Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 97%

“…(Scheme 1), 6 which can bring about an exchange reaction. From the biological point of view, this exchange reaction diselenide-selenol/ thiol-disulfide can be considered a futile cycle that can lead to thiol depletion.…”

Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 99%

“…6 Indeed, as discussed briefly above, the pharmacological properties of ebselen and diphenyl diselenide can be associated with their antioxidant activities that greatly rely in the formation of a selenol group after interaction with reducing thiols. 6 The thiol peroxidase-like activity of diphenyl diselenide and analogs can be easily demonstrated in pure in vitro chemical models. 6 However, the occurrence of such type of reaction after in vivo administration or even in vitro using simple biological systems is difficult to determine.…”

Section: Molecular Pharmacology Of Diphenyl Diselenidementioning

confidence: 99%

“…6 In this review, we will present the main molecular aspects related to the in vitro toxicity and pharmacology of diphenyl diselenide and also will provide in vivo data indicating that the interaction of diphenyl diselenide with thiols can dictate either its toxicological or pharmacological property.…”

Section: Introductionmentioning

confidence: 99%

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Diphenyl diselenide a janus-faced molecule

Nogueira

Rocha

2010

J. Braz. Chem. Soc.

198

105

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Este artigo de revisão aborda uma reflexão sobre o potencial terapêutico ou tóxico de compostos orgânicos de selênio, dando particular ênfase ao disseleneto de difenila e alguns dos seus análogos estruturais. Algumas características moleculares relacionadas com a toxicidade e farmacologia do disseleneto de difenila in vitro e in vivo são abordadas. Os artigos revisados, que abordam experimentos in vivo, indicam que a interação do disseleneto de difenila com tióis pode determinar seu potencial farmacológico ou toxicológico. Além disso, uma limitada ativação da rota de toxicidade, isto é, a oxidação controlada de moléculas de alto peso molecular, que contém grupos tióis, poderia contribuir para os efeitos farmacológicos do disseleneto de difenila. Concluise que a síntese de compostos orgânicos de selênio deve ser direcionada para o desenvolvimento de novos disselenetos de diorganoila que possam interagir com alvos moleculares específicos.In this review, we summarized the potential role of synthetic organoseleno compounds as therapeutic or toxic agents, giving emphasis almost exclusively to diphenyl diselenide, the simplest of the diaryl diselenides, and some of its analogs. We presented the main molecular aspects related to the in vitro toxicity and pharmacology of diphenyl diselenide and also provided in vivo data indicating that the interaction of diphenyl diselenide with thiols can dictate either its toxicological or pharmacological property. The papers covered in this review indicate that a limited activation of the "toxic pathway", i.e., a controlled oxidation of specific high molecular weight thiol-containing molecules could contribute to the pharmacological effects of diphenyl diselenide. In conclusion, this review reinforces the necessity of developing new diorganoyl diselenides that could interact with specific molecular targets.

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Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 97%

Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 99%

Section: Molecular Pharmacology Of Diphenyl Diselenidementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Diphenyl diselenide a janus-faced molecule

Nogueira

Rocha

2010

J. Braz. Chem. Soc.

198

105

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“…The concept that selenium-containing molecules may be better nucleophiles (and therefore antioxidants) than classical antioxidants have led to design synthetic organoselenium compounds. 14 [15][16][17][18][19][20] Evidence in the literature indicates that (PhSe) 2 reduces lipid peroxidation induced by a variety of oxidants 21 by displaying thiol peroxidase-like activity 15,22 and acting in different antioxidant lines of defense. [16][17][18] The assumption that acute physical exercise increases RONS generation and could induce oxidative stress motivated the present study.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant effect of diphenyl diselenide on oxidative stress caused by acute physical exercise in skeletal muscle and lungs of mice

Prigol

Luchese

Nogueira

2009

Cell Biochemistry & Function

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This study was designed to examine if diphenyl diselenide (PhSe) 2 , an organoselenium compound, attenuates oxidative stress caused by acute physical exercise in skeletal muscle and lungs of mice. Swiss mice were pre-treated with (PhSe) 2 (5 mg kg -1 day -1 ) for 7 days. At the 7th day, the animals were submitted to acute physical exercise which consisted of continuous swimming for 20 min. The animals were euthanized 1 and 24 h after the exercise test. The levels of thiobarbituric acid reactive species (TBARS), non-protein thiols (NPSH) and ascorbic acid and the activity of catalase (CAT) were measured in the lungs and skeletal muscle of mice. Glycogen content was determined in the skeletal muscle of mice. Parameters in plasma (urea and creatinine) were determined. The results demonstrated an increase in TBARS levels induced by acute physical exercise in the skeletal muscle and lungs of mice. Animals submitted to exercise showed an increase in non-enzymatic antioxidant defenses (NPSH and ascorbic acid) in the skeletal muscle. In lungs of mice, activity of CAT was increased. (PhSe) 2 protected against the increase in TBARS levels and ameliorated antioxidant defenses in the skeletal muscle and lungs of mice submitted to physical exercise. These results indicate that acute physical exercise caused a tissue-specific oxidative stress in the skeletal muscle and lungs of mice. (PhSe) 2 protected against oxidative damage induced by acute physical exercise in mice.

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Theoretical Aspects of Organoselenium Chemistry

Sunoj

2011

Patai's Chemistry of Functional Groups

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The chapter offers an overview of the applications of theoretical methods in the area of organoselenium chemistry. In recent years, the availability of reliable basis sets and computational methods, especially the emergence of density functional methods, have enabled studies on increasingly complex chemical problems. A plethora of such problems in organoselenium chemistry and interesting insights on structure, properties, and reactions derived by using computational methods constitute the contents of this chapter. The types of situations described range from exotic briefly lived intermediates to structural and electronic features of stable and crystalline molecules. Properties such as nuclear magnetic resonance chemical shift and the comparison between computed and experimental quantities have been provided extensively. A number of reactions of selenium compounds with emphasis on biologically significant reactions have been highlighted. In particular, computational studies on glutathione peroxidate activity of selenium compounds have been elaborated. The electronic origins of inter‐ and intra‐molecular nonbonding interactions in organoselenium compounds and an illustration of how theoretical methods have been vital in quantifying such weak interactions have been provided.

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Organoselenium and Organotellurium Compounds: Toxicology and Pharmacology

Cited by 1,658 publications

References 380 publications

Diphenyl diselenide a janus-faced molecule

Diphenyl diselenide a janus-faced molecule

Antioxidant effect of diphenyl diselenide on oxidative stress caused by acute physical exercise in skeletal muscle and lungs of mice

Theoretical Aspects of Organoselenium Chemistry

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