Diphenyl diselenide and diphenyl ditelluride differentially affect ?-aminolevulinate dehydratase from liver, kidney, and brain of mice

Maciel, Evelise N.; Bolzan, Rodrigo Cordeiro; Braga, Antônio L.; Rocha, João B. T.

doi:10.1002/1099-0461(2000)14:6<310::aid-jbt3>3.0.co;2-d

Cited by 130 publications

(54 citation statements)

References 67 publications

(72 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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: 96%

“…10,11,13 Indeed, the interaction of diphenyl diselenide with insect, fish and mammalian δ-ALA-D and other thiolcontaining enzymes or proteins, such as Na + ,K + -ATPase and vicinal mitochondrial thiol containing proteins, can be facilitated by the proximity or by the presence of vicinal thiol groups in their tertiary structure (Figure 4). [13][14][15] Taken together, these in vitro results can indicate that high molecular weight containing-molecules, i.e., specific classes of proteins or enzymes can be preferential targets of diphenyl diselenide and analogs than GSH.…”

Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 99%

“…Accordingly, acute or sub-acute exposure to diphenyl diselenide caused a more marked decrease in hepatic or cerebral δ-ALA-D activity than in NPSH levels. 11 Considering the importance of GSH content in maintaining the intracellular redox balance, we have investigated the effect of diphenyl diselenide on this low molecular weight endogenous thiol in different tissues of rodents. A single subcutaneous administration of diphenyl diselenide decreased the plasmatic levels of NPSH in mice.…”

Section: Decrease Of Low-molecular Weight Thiol Levelsmentioning

confidence: 99%

“…36 In a sub-acute protocol, mice exposed for 14 days to diphenyl diselenide, presented a significant reduction in liver NPSH content. 11 Rosa and co-workers 37 have demonstrated that a single exposure with diphenyl diselenide significantly reduced the concentration of reduced form of intracellular glutathione but did not increase that of the oxidized form GSSG. Apparently, high doses of diphenyl diselenide administered by intraperitoneal route depleted GSH in mice organs and tissues, therefore increasing the ratio GSSG/GSH.…”

Section: Decrease Of Low-molecular Weight Thiol Levelsmentioning

confidence: 99%

“…11 The inhibition of δ-ALA-D activity by diphenyl diselenide has been reported to be dependent on the time of exposure (acute or sub-acute), dose and tissue. In this way, acute or sub-acute administration of diphenyl diselenide inhibited erythrocytic, hepatic and cerebral δ-ALA-D activities in mice.…”

Section: Inhibition Of D-ala-d Activity Following Exposure To Diphenymentioning

confidence: 99%

See 4 more Smart Citations

Diphenyl diselenide a janus-faced molecule

Nogueira

Rocha

2010

J. Braz. Chem. Soc.

199

106

View full text Add to dashboard Cite

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.

show abstract

Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 96%

Section: Molecular Toxicology Of Diphenyl Diselenidementioning

confidence: 99%

Section: Decrease Of Low-molecular Weight Thiol Levelsmentioning

confidence: 99%

Section: Decrease Of Low-molecular Weight Thiol Levelsmentioning

confidence: 99%

Section: Inhibition Of D-ala-d Activity Following Exposure To Diphenymentioning

confidence: 99%

See 3 more Smart Citations

Diphenyl diselenide a janus-faced molecule

Nogueira

Rocha

2010

J. Braz. Chem. Soc.

199

106

View full text Add to dashboard Cite

show abstract

Organoselenium and organotellurium compounds: Toxicology and pharmacology

Nogueira

Rocha

2011

Patai's Chemistry of Functional Groups

View full text Add to dashboard Cite

In the last three decades, the interest in the field of synthesis and reactivity of organoselenium and organotellurium compounds has increased; particularly, in view of the observations that they can exhibit important biological activities. The data presented in this chapter clearly indicate the potential pharmacological and therapeutic uses of organoselenium and organotellurium compounds. Indeed, these classes of molecules exhibit a variety of interesting biological effects, namely antioxidant properties, which can account for their in vitro and in vivo beneficial effects in a wide range of models of different human pathologies. We can conclude that the future of “medicinal chemistry“ of organoselenium and organotellurium compounds will depend on the rational development of new molecules, which can be guided by chemical and biological approaches. Moreover, the structure‐activity relationship for a given class of organoselenium or organotellurium compounds should be used as a toll for screening molecules with high probability of exhibiting low toxicity and high pharmacological activity in mammals.

show abstract

Synthesis of tellurium containing syndiotactic polymethyl methacrylate using diphenyl ditelluride as a novel initiator

Tripathi

Srivastava

Khandelwal

2006

J of Applied Polymer Sci

View full text Add to dashboard Cite

ABSTRACT:The synthesis of syndiotactic polymethyl methacrylate containing tellurium by using diphenyl ditelluride in the dioxan at (60 Ϯ 0.1)°C for 2 h has been carried out. The presence of tellurium in the polymer has been confirmed qualitatively as well as by induced coupled plasma mass spectroscopy (ICP-MS). The electron spin resonance spectrum shows the presence of Tė Ph, and value of gyromagnetic constant g has been calculated as 2.2203. The T g of the polymer, measured by DSC, is 105°C. The syndiotactic nature has been confirmed by FTIR and NMR spectroscopy and DSC. The system follows ideal kinetics with activation energy 66 kJ mol Ϫ1 .

show abstract

Diphenyl diselenide and diphenyl ditelluride differentially affect ?-aminolevulinate dehydratase from liver, kidney, and brain of mice

Cited by 130 publications

References 67 publications

Diphenyl diselenide a janus-faced molecule

Diphenyl diselenide a janus-faced molecule

Organoselenium and organotellurium compounds: Toxicology and pharmacology

Synthesis of tellurium containing syndiotactic polymethyl methacrylate using diphenyl ditelluride as a novel initiator

Contact Info

Product

Resources

About