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PubMed2003

Functional diversity of the rhodanese homology domain: the Escherichia coli ybbB gene encodes a selenophosphate-dependent tRNA 2-selenouridine synthase.

Escherichia coli has eight genes predicted to encode sulfurtransferases having the active site consensus sequence Cys-Xaa-Xaa-Gly. One of these genes, ybbB, is frequently found within bacterial operons that contain selD, the selenophosphate synthetase gene, suggesting a role in selenium metabolism. We show that ybbB is required in vivo for the specific substitution of selenium for sulfur in 2-thiouridine residues in E. coli tRNA. This modified tRNA nucleoside, 5-methylaminomethyl-2-selenouridine (mnm(5)se(2)U), is located at the wobble position of the anticodons of tRNA(Lys), tRNA(Glu), and tRNA(1)(Gln). Nucleoside analysis of tRNAs from wild-type and ybbB mutant strains revealed that production of mnm(5)se(2)U is lost in the ybbB mutant but that 5-methylaminomethyl-2-thiouridine, the mnm(5)se(2)U precursor, is unaffected by deletion of ybbB. Thus, ybbB is not required for the initial sulfurtransferase reaction but rather encodes a 2-selenouridine synthase that replaces a sulfur atom in 2-thiouridine in tRNA with selenium. Purified 2-selenouridine synthase containing a C-terminal His(6) tag exhibited spectral properties consistent with tRNA bound to the enzyme. In vitro mnm(5)se(2)U synthesis is shown to be dependent on 2-selenouridine synthase, SePO(3), and tRNA. Finally, we demonstrate that the conserved Cys(97) (but not Cys(96)) in the rhodanese sequence motif Cys(96)-Cys(97)-Xaa-Xaa-Gly is required for 2-selenouridine synthase in vivo activity. These data are consistent with the ybbB gene encoding a tRNA 2-selenouridine synthase and identifies a new role for the rhodanese homology domain in enzymes.

Amino Acid Sequence↗
PubMed2006

Alpha-selenoconotoxins, a new class of potent alpha7 neuronal nicotinic receptor antagonists.

Disulfide bonds are important structural motifs that play an essential role in maintaining the conformational stability of many bioactive peptides. Of particular importance are the conotoxins, which selectively target a wide range of ion channels that are implicated in numerous disease states. Despite the enormous potential of conotoxins as therapeutics, their multiple disulfide bond frameworks are inherently unstable under reducing conditions. Reduction or scrambling by thiol-containing molecules such as glutathione or serum albumin in intracellular or extracellular environments such as blood plasma can decrease their effectiveness as drugs. To address this issue, we describe a new class of selenoconotoxins where cysteine residues are replaced by selenocysteine to form isosteric and nonreducible diselenide bonds. Three isoforms of alpha-conotoxin ImI were synthesized by t-butoxycarbonyl chemistry with systematic replacement of one ([Sec(2,8)]ImI or [Sec(3,12)]ImI), or both ([Sec(2,3,8,12)]ImI) disulfide bonds with a diselenide bond. Each analogue demonstrated remarkable stability to reduction or scrambling under a range of chemical and biological reducing conditions. Three-dimensional structural characterization by NMR and CD spectroscopy indicates conformational preferences that are very similar to those of native ImI, suggesting fully isomorphic structures. Additionally, full bioactivity was retained at the alpha7 nicotinic acetylcholine receptor, with each selenoanalogue exhibiting a dose-response curve that overlaps with wild-type ImI, thus further supporting an isomorphic structure. These results demonstrate that selenoconotoxins can be used as highly stable scaffolds for the design of new drugs.

Amino Acid Sequence↗
PubMed1981

The excretion of selenium in bile and urine of steers: the influence of form and amount of Se salt.

1. The excretion of 75Se and stable Se in bile and urine was measured in four steers during 6 h after intravenous injections of 75Se as either selenite or selenate containing either 5 or 5000 microgram carrier Se. 2. When 5000 microgram Se were given, the rate of urinary excretion and plasma clearance of 75SE was similar for both salts. Approximately 23% was excreted in urine and plasma clearance was triexponential, the mean half-life (t 1/2) of the successive components, alpha, beta, and gamma, being 2.3, 15-2 and 465 min respectively. The amount of 75Se excreted in bile was small; 1.94% of the 75SeO3(2-) and 0.86% of the 75SeO4(2-) dose. 3. When 5 microgram Se were given the plasma clearance of 75Se was initially biexponential but the entry of 75Se-labelled protein from the liver caused an increase in plasma radioactivity after 30-40 min. The effect was most marked after 5 microgram 75SeO3(2-) when plasma 75Se radioactivity returned to 69% of the activity present at 2 min. Values for t 1/2 of the two components of clearance for 75SEO4(2-) were respectively alpha 2.6 and 2.5 min, and beta 15.9 and 36.6 min. Similar amounts of 75Se appeared in bile (0.2% of the dose) after injection of either salt but much less 75Se was excreted in urine after 75SeO3(2-) (6%) than after 75SeO4(2-) (17%). 4. At low dosage rates (5 microgram) Se is more readily incorporated into tissues from SeO3(2-) than from SeO4(2-).

Animals↗
PubMed1987

Relative nutritional availability to rats of selenium in Finnish spring wheat (Triticum aestivum L.) fertilized or sprayed with sodium selenate and in an American winter bread wheat naturally high in Se.

A Finnish national programme to fertilize crops with sodium selenate led us to compare the nutritional availability to rats of selenium in two Finnish spring wheats (Triticum aestivum L.), either fertilized or sprayed with sodium selenate, with that in an American winter bread wheat naturally high in Se. Weanling male rats were given a Se-deficient Torula yeast diet for 4 weeks followed by either continued depletion or repletion for 4 weeks with graded levels of Se as sodium selenite (standard) or wheat (test food). Plasma and liver Se levels and plasma and liver glutathione peroxidase (EC 1.11.1.9; GSH-Px) activities were used as criteria of body Se status. The availability of Se under these conditions was calculated with the point-slope technique at two dietary levels of Se (Expt 1) and with the slope-ratio method (Expt 2). In the point-slope assay, the level of dietary Se fed had a considerable effect on the apparent availability values obtained which made interpretation of the results difficult. In the slope-ratio assay, no difference in the availability of Se from the various wheats was observed when plasma or liver Se levels were used as the response criteria. The Se in the fertilized wheat was somewhat more available than that in the sprayed wheat when plasma or liver GSH-Px activities were the response criteria. Overall, availability values (%) derived by averaging all four response criteria were 86, 77 and 73 for the fertilized and sprayed Finnish wheats and the American wheat respectively (sodium selenite 100). These results show that wheat is a relatively available source of Se to rats regardless of whether its Se content is naturally high or is increased by fertilization or spraying.

Animals↗
PubMed1993

Long-term supplementation with selenate and selenomethionine: selenium and glutathione peroxidase (EC 1.11.1.9) in blood components of New Zealand women.

Thirty-three New Zealand women aged 18-23 years received daily for 32 weeks, 200 micrograms Se as Se-enriched yeast (selenomethionine), or brewer's yeast mixed with selenate, or no added Se (placebo) in a double-blind trial. Se supplementation raised (P = 0.001) platelet glutathione peroxidase (EC 1.11.1.9; GSHPx) activity, and also Se and GSHPx in whole blood, erythrocytes and plasma. Selenomethionine was more effective in raising blood Se concentrations than selenate, but both were equally effective in raising GSHPx activities in whole blood, erythrocytes and plasma, indicating a similar bioavailability for the two forms. These observations and those of gel filtration studies of erythrocytes and plasma proteins reported elsewhere (Butler et al. 1991) are consistent with the incorporation of Se from selenomethionine into a general tissue protein pool while selenate is directly available for GSHPx synthesis, and explain the poorer correlation between Se and GSHPx in individuals with higher Se status. However, selenate raised platelet GSHPx activities to a greater extent than did selenomethionine suggesting some other effect of selenate on platelets which needs further investigation. A response of GSHPx activity in these New Zealand subjects indicates that their dietary Se intake is insufficient to meet recommended intakes based on the criterion of saturation of GSHPx activity, and could reflect a marginal Se status. The level of blood Se necessary for saturation of GSHPx of about 100 ng Se/ml whole blood confirms observations in earlier studies.

Adolescent↗
PubMed1997

Long-term supplementation with selenate and selenomethionine: urinary excretion by New Zealand women.

Thirty-six New Zealand women aged between 18 and 23 years received daily for 32 weeks, 200 micrograms Se as Se-enriched yeast (selenomethionine, SeMet), or brewer's yeast mixed with selenate, or no added Se (placebo) in a double-blind trial. Mean daily Se excretion increased with both supplements; the selenate group excreted more than the SeMet group, 123 v. 66 micrograms/d respectively at week 2, equivalent to 57 v. 27% of the dose. Thereafter Se output increased for the SeMet group reaching a plateau at about 100 micrograms/d at week 16, when plasma Se had also plateaued at 190 ng/ml. The selenate group had reached an earlier plateau of 110 ng Se/ml at week 7. There was a close relationship between 24 h urine and plasma Se for the SeMet group but not for the selenate group. Renal plasma clearances showed two distinctly different responses; the clearance of 0.4 ml/min reached by the SeMet group at week 2 plateaued as plasma Se increased almost 2-fold; whereas for the selenate group the clearance varied between 0.8 and 1.1 ml/min whilst plasma Se remained almost constant at 110 ng/ml. Previous studies, also of 200 micrograms Se/d as Se-rich bread, in New Zealand (NZ) and elsewhere showed similar responses to Se-yeast; the selenite response was intermediate between selenate and Se-yeast (SeMet). The full significance of these studies awaits identification of Se components in plasma, glomerular filtrate and urine; meanwhile renal clearances serve as a pointer to changes in the distribution of Se-containing fractions in the plasma. Trimethylselenonium was detected in basal urines, and was a minor component in urines of supplemented NZ subjects at about 1% of the total Se.

Adolescent↗
PubMed1998

Selenate- and selenomethionine-induced leukopenia in ICR female mice.

The investigations reported here were conducted to gain a better understanding of the comparative toxicity of selenium. Sodium selenate and selenomethionine were administered to young adult ICR female mice. Peripheral leukocyte counts and ratios of agranulocyte (Ag) to granulocyte (G) leukocytes were determined from blood that was collected at regularly scheduled intervals. Data indicated that both forms of selenium induced a transient yet marked decrease in the number of circulating leukocytes (leukopenia) following serial injections (2 mg Se/kg/injection). The leukopenia was more extensive and of a greater duration for selenomethionine-treated mice. For selenate-injected animals the Ag/G ratio increased sharply while the ratio shift for selenomethionine-injected mice was significantly less. Data are interpreted in regard to the different possible modes of action of selenate and selenomethionine on peripheral leukocytes causing leukopenia and the variable Ag/G ratio values.

Animals↗
PubMed2001

Nutritional selenium supplements: product types, quality, and safety.

Selenium supplements contain selenium in different chemical forms. In the majority of supplements, the selenium is present as selenomethionine. However, in multivitamin preparations, infant formulas, protein mixes, weight-loss products and animal feed, sodium selenite and sodium selenate are predominantly used. In some products, selenium is present in protein- or amino acid chelated forms; in still others, the form of selenium is not disclosed. Current evidence favors selenomethionine over the other forms of selenium. Extradietary supplementation of selenium at the dosage of 200 micrograms per day is generally considered safe and adequate for an adult of average weight subsisting on the typical American diet.

Anticarcinogenic Agents↗
PubMed2002

Selenocompounds in plants and animals and their biological significance.

There are several selenocompounds in tissues of plants and animals. Selenate is the major inorganic selenocompound found in both animal and plant tissues. Selenocysteine is the predominant selenoamino acid in tissues when inorganic selenium is given to animals. Selenomethionine is the major selenocompound found initially in animals given this selenoamino acid, but is converted with time afterwards to selenocysteine. Selenomethionine is the major selenocompound in cereal grains, grassland legumes and soybeans. Selenomethionine can also be the major selenocompound in selenium enriched yeast, but the amount can vary markedly depending upon the growth conditions. Se-methylselenocysteine is the major selenocompound in selenium enriched plants such as garlic, onions, broccoli florets and sprouts, and wild leeks.

Animals↗
PubMed2002

One-electron oxidation of plasmid DNA by selenium(V) species.

PURPOSE: To employ the gamma-radiation-generated selenium(V) one-electron-oxidizing agent SeO3*- for the preparation of guanyl radicals in plasmid DNA, and to compare the behaviour of this reagent with that of other similarly reactive oxidant species. MATERIALS AND METHODS: Plasmid DNA in aerobic aqueous solution was irradiated with 137Cs gamma-rays (662 keV). The solutions also contained up to 4x10(-2) mol x dm(-3) sodium selenate (Na2SeO4) and/or up to 10(-1) mol x dm(-3) sodium biselenite (NaHSeO3), as well as auxiliary scavengers such as DMSO or glycerol. In some cases, reducing agents such as ferrocyanide were also present. After irradiation, the plasmid was incubated with the Escherichia coli base excision-repair endonuclease formamidopyrimidine-DNA N-glycosylase (FPG). These treatments produced strand breaks in the plasmid. The yields of these strand breaks were quantified by agarose gel electrophoresis. RESULTS: In general, gamma-irradiation produced single-strand breaks (SSB) in plasmid DNA. Subsequent incubation with the endonuclease FPG increased the SSB yield by a factor of 2-100-fold. The smallest effects of FPG were observed when only DMSO or glycerol were present during irradiation. FPG incubation produced significantly larger increases in the SSB yield after gamma-irradiation in the additional presence of selenate and/or biselenite. The largest effect of FPG was observed after gamma-irradiation in the presence of 10(-2) mol x dm(-3) sodium selenate and 10(-1) mol x dm(-3) glycerol. This was indicative of extensive oxidative damage to the plasmid under these conditions and provided evidence for guanine oxidation mediated by SeO3*-. The large effect of FPG was strongly attenuated by the addition of reducing agents such as ferrocyanide. The observations suggest that these reducing agents exert their effects through the reduction of an intermediate guanyl radical. CONCLUSION: By comparing the yields of breaks produced after gamma-irradiation under a range of conditions, it is possible to formulate a reaction scheme that describes the chemical reactions responsible for the formation of strand breaks and FPG-sensitive sites. By applying this scheme to the data, we can quantify rate constants for the reduction of DNA guanyl radicals by reducing agents. This reaction is of particular interest to radiation biology because it is the equivalent of the repair of DNA damage by the direct effect of ionizing radiation.

Binding Sites↗
PubMedDate not supplied

New 3'-deoxythymidines bearing a nucleophilic 3'-substituent.

New potential cancer-driven as well as HIV-driven nucleoside heteroanalogs, such as 3'-thio- and 3'- as well as 5'-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for 3'-alpha-alkylthiothymidines.

Anti-HIV Agents↗
PubMed2001

Synthesis and stereochemical characterization of diastereomeric nucleoside-phosphorothioselenoates by NMR methods.

Synthesis and stereochemical characterization of enantiomerically pure nucleoside-phosphorothioselenoates are reported. The effects of solvent and temperature on the vicinal carbon-phosphorus couplings are described and the results are interpreted in terms of conformational changes influenced by stacking interactions between the bases and the phenyl rings.

Hydrophobic and Hydrophilic Interactions↗
PubMed2001

Synthesis of selenium-derivatized nucleosides and oligonucleotides for X-ray crystallography.

We report here the synthesis of nucleoside and oligonucleotide analogs containing selenium, which serves as an anomalous scattering center to enable MAD phase determination in nucleotide X-ray crystallography. We have developed a phase transfer approach to introduce the selenium functionality in A, C, G, T, and U nucleosides at 5'-positions. In the incorporation of the selenium functionality, the leaving groups (bromide, mesyl, and tosyl) were readily displaced by sodium selenide, sodium diselenide, and sodium methyl selenide with yields higher than 90%. Selenium-derivatized oligonucleotides have been synthesized via phosphoramidite chemistry.

Crystallography, X-Ray↗
PubMedDate not supplied

Selenium improves cardiac function by attenuating the activation of NF-kappaB due to ischemia-reperfusion injury.

Although selenium, an essential trace element and a component of glutathione peroxidase, is known to protect the heart from ischemia-reperfusion (I/R)-induced injury, the mechanisms of this protection are not fully understood. For this purpose, isolated rat hearts were subjected to 30 min of global ischemia followed by 30 min of reperfusion; sodium selenite (25-1,000 nM) was added in the perfusion medium 10 min prior to ischemia, as well as during reperfusion. Selenium caused a dose-dependent improvement in cardiac performance and attenuated the decrease in the ratio of reduced glutathione to oxidized glutathione, as well as the increased level of malondialdehyde in I/R heart. Elevated ratios of nuclear factor-kappaB (NF-kappaB) in particulate and cytosolic fraction and of phosphorylated NF-kappaB and total NF-kappaB in I/R hearts were reduced by selenium. Cardiac dysfunction in hearts perfused with xanthine plus xanthine oxidase mixture, as well as hydrogen peroxide, or subjected to Ca2+ paradox was also attenuated by selenium. These data suggest that selenium protects the heart against I/R injury due to its action on the redox state and deactivation of NF-kappaB in I/R hearts.

Animals↗
PubMed1986

Urinary and fecal excretions and absorption of a large supplement of selenium: superiority of selenate over selenite.

A correction needs to be made to the form of selenium used in earlier studies; what was believed to be selenite-Se in solution is now known to have been selenate-Se. In the present study, excretion of Se was followed in 13 women after ingestion of 1 mg Se as selenite or selenate in solution. Fecal excretion of selenate-Se was less than for selenite-Se reflecting a higher apparent absorption [94 +/- 4% (SD), 62 +/- 14%, respectively]. Peak excretion of Se occurred 3 h earlier for selenate-Se than for selenite-Se and was 6 times higher. Total urinary excretion of selenate-Se was 3 times that of selenite-Se and still 2 times as high when expressed as % absorbed dose. Total recovery of Se in urine and feces was similar for both forms. There was remarkable agreement between these results and those reported earlier for selenate-Se (Selovet-1) and selenite-Se.

Adult↗