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PubMed2001

Benzo[2,1-c:3,4-c']bis(1,2,3-thiaselenazole) (BSe) and its charge trasfer chemistry. Crystal and electronic structure of [BSe]3[ClO4]2.

The S-Se-N-based heterocycle benzo[2,1-c:3,4-c']bis(1,2,3-thiaselenazole) (BSe) can be prepared by the condensation of 1,4-diaminobenzene-2,3-dithiol with selenium tetrachloride. Crystals of this compound are not isomorphous with the related benzo[2,1-c:3,4-c']bis(1,2,3-dithiazole) (BT); a structure is adopted that allows for more extensive intermolecular Se- - -Se contacts. Electro-oxidation of BSe in the presence of [n-Bu4N][ClO4] affords metallic green needles of the charge transfer salt [BSe]3[ClO4]2, which exhibit a pressed pellet conductivity sigma(RT) = 10(-1) S cm(-1). The crystal structure of [BSe]3[ClO4]2 consists of slipped pi-stacks based on the triple-decker closed shell [BSe]3(2+) building block. The packing is analogous to that found for the charge transfer salt [BT]3[FSO3]2, for which sigma(RT) = 10(-2) S cm(-1). Extended Hückel band structure calculations on these two (sulfur- and selenium-based) 3:2 salts reveal more extensive intermolecular interactions in the selenium compound. As a result, the latter has a more two-dimensional electronic structure. Crystal data for Se2S2N2C6H2, a = 4.103(2) A, b = 12.159(2) A, c = 16.171(2) A, orthorhombic, Pbnm, Z = 4. Crystal data for Se6S6N6C18H6Cl2O4, a =17.00(1) A, b = 18.36(1) A, c = 10.679(4) A, 110.27(3), monoclinic, C2/c, Z = 4.

Journal Article↗
PubMed1982

Aerobic, Selenium-Utilizing Bacillus Isolated from Seeds of Astragalus crotalariae.

Bacillus sp. strain SS, an aerobic, gram-positive sporeformer, was isolated from seeds of Astragalus crotalariae, a selenium-accumulating plant. This bacillus grew in a nutrient broth (containing beef extract and peptone) if the medium was supplemented with high concentrations of selenium. Concentrations of Na(2)SeO(3) that supported growth ranged from 3 to 100 mM. After 24 h of growth, the culture developed a deep red color characteristic of elemental selenium. When selenium was provided in the form of selenate, the pattern of growth showed a prolonged lag period, from 24 to 48 h. Final growth remained below that of cells cultured in the presence of selenite, and only a light red color developed. Concentrations of selenate below 40 mM failed to support growth. Tellurate, though not tellurite, could replace selenite, but only over a narrow concentration range, 5 to 10 mM. By 24 h, the typical black color of elemental tellurium developed. Bacillus sp. strain SS grew also in brain heart infusion broth and Trypticase soy broth (BBL Microbiology Systems, Cockeysville, Md.) without the addition of selenium or tellurium compounds. When added to these media, 50 mM selenite was tolerated and metabolized by the organism. The crucial distinction between this bacillus and other selenium-tolerant organisms (e.g., Salmonella) remains: under certain conditions, growth requirements of Bacillus sp. strain SS are fulfilled by selenium (and tellurium) compounds.

Journal Article↗
PubMed2004

Tin-chalcogen double-bond compounds, stannanethione and stannaneselone: synthesis, structure, and reactivities.

The first isolation of diarylstannanethione (tin-sulfur double-bond compound) and diarylstannaneselone (tin-selenium double-bond compound), Tbt(Ditp)Sn=X (Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; Ditp = 2,2' '-diisopropyl-m-terphenyl-2'-yl; X = S and Se) was accomplished by dechalcogenation of the corresponding highly hindered tetrachalcogenastannolanes, Tbt(Ditp)SnX(4). The (119)Sn NMR of stannanethione, Tbt(Ditp)Sn=S, and stannaneselone, Tbt(Ditp)Sn=Se, showed only one low-field broad signal at 531 and 440 ppm, respectively, characteristic of a tricoordinated tin, and hence, the stannanethione and stannaneselone display an intrinsic nature of tin-chalcogen double-bond compounds. The X-ray crystallographic analysis of the isolated stannaneselone, Tbt(Ditp)Sn=Se 5a, revealed a completely trigonal geometry around the central tin with a remarkably short Sn-Se bond length, indicative of structural similarity to a ketone.

Journal Article↗
PubMed1997

Chemoprevention of colon cancer by organoselenium compounds and impact of high- or low-fat diets.

BACKGROUND: Observational and experimental studies have suggested that dietary supplementation with selenium can inhibit the development of colon cancer. However, many forms of selenium are toxic. Consequently, the development of efficacious compounds with low toxicity has been pursued. PURPOSE: Two synthetic organoselenium compounds, p-methoxy-benzyl selenocyanate (p-methoxy-BSC) and 1,4-phenylenebis(methylene)selenocyanate (p-XSC), were tested for their ability to inhibit colon carcinogenesis in rats that were treated with the carcinogen azoxymethane and fed low- or high-fat diets. METHODS: Groups of 5-week-old male F344 rats (42 animals/ group) were fed either a high-fat diet or a low-fat diet with or without added p-methoxy-BSC (10 or 20 parts per million [ppm]) or p-XSC (20 ppm). Two weeks later, 30 animals in each group received a subcutaneous injection of azoxymethane (15 mg/kg body weight); 1 week later, they received a second injection. The remaining 12 rats in each group received two injections of saline. Three days after the second injection of carcinogen or saline, animals being fed diets with p-methoxy-BSC or p-XSC were switched to corresponding organoselenium-free low- or high-fat diets for the remainder of the study to determine the effects of the selenium compounds on the initiation phase of colon carcinogenesis. At that time, groups of animals that had been maintained on organoselenium-free low- or high-fat diets were switched to diets containing p-methoxy-BSC or p-XSC until the end of the study to determine the effects of these compounds on the postinitiation phase of colon carcinogenesis. All animals were killed during the 38th week after azoxymethane or saline treatment, and histopathologic analysis of the colon tumors was performed. Colon tumor incidence and multiplicity were analyzed statistically. RESULTS: No obvious toxic effects were observed following dietary administration of 10 or 20 ppmp-methoxy-BSC or 20 ppm p-XSC. Administration of 20 ppm p-methoxy-BSC in a high-fat diet during the initiation and postinitiation phases of colon carcinogenesis significantly (statistically) reduced colon tumor incidence; 10 ppmp-methoxy-BSC in a high-fat diet significantly reduced colon tumor incidence but only when it was given during the postinitiation phase. Colon tumor incidence was also significantly reduced when 20 ppm p-XSC was given in a high-fat diet during the initiation phase of colon carcinogenesis. When 20 ppm p-XSC was administered in either a high-fat diet or a low-fat diet during the postinitiation phase, both colon tumor incidence and multiplicity were significantly reduced; the greatest reductions were in animals fed a low-fat diet. CONCLUSIONS: In this model system, p-methoxy-BSC and p-XSC are effective agents for the chemoprevention of colon cancer. The effects of p-XSC were enhanced in animals fed a low-fat diet.

Adenocarcinoma↗
PubMed2004

Mechanisms of mammary cancer chemoprevention by organoselenium compounds.

Searching for optimal diets and for naturally occurring agents in routinely consumed foods that may inhibit cancer development, although challenging, constitutes a valuable and plausible approach to finding ways to control and prevent cancer. To date, the use of the micronutrient selenium in human clinical trials is limited but the outcome of these investigations indicates that selenium is one of the most promising agents. Data presented in this mini-review indicate that the dose and the form (structure) in which selenium is used are the most critical determinants of success in future clinical trials. The focus of this mini-review is on the mechanisms of mammary cancer chemoprevention by organoselenium compounds. Among the naturally occurring organoselenium compounds, Se-Methylselenocysteine is more efficacious than the most extensively studied forms, such as selenomethionine. However, we showed that synthetic organoselenium compounds can be tailored to achieve greater chemopreventive efficacy with minimal side effects by structural modifications; it is evident that synthetic agents are superior to the inorganic selenite, naturally occurring selenium compounds and their sulfur-containing analogs. We have demonstrated that 1,4-phenylenebis (methylene) selenocyanate (p-XSC) and its putative metabolite glutathione conjugate (p-XSeSG) are highly promising agents in the chemoprevention of mammary carcinogenesis in the 7,12-dimethylbenz[a]anthracene (DMBA)-rat mammary tumor model system. Both compounds inhibit the initiation phase of carcinogenesis by inhibiting DMBA-DNA adduct formation in the target organ in vivo. cDNA microarray analysis indicates that both selenium compounds alter genes in a manner that leads to inhibition of cell proliferation and induction of apoptosis; modulation of apoptosis and cell proliferation can account for chemoprevention during the post-initiation phase of mammary carcinogenesis. Using a rat mammary cancer cell line, we compared p-XSC and p-XSeSG as inhibitors of cell proliferation; depending on the selenium dose and time point selected, p-XSC was comparable to or better than p-XSeSG. Collectively, the results described here, suggest that the molecular targets modulated by organoselenium compounds are highly useful indicators of success in clinical cancer chemoprevention trials.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed2001

A novel reactivity of SeO(2) with 1,3-dienes: formation of syn 1,2- and 1,4-diols via a facile C-Se bond oxidation.

[reaction: see text] A novel reaction between 1,3-dienes and selenium dioxide to give syn 1,2- and 1,4-diol cyclic selenites was studied in detail. This study indicates that an initial concerted [4 + 2] cycloaddition followed by a stereospecific carbon-selenium bond oxidation is involved in this unprecedented syn dihydroxy addition reaction mediated by selenium dioxide.

Alcohols↗
PubMed2005

Quantification and speciation of mercury and selenium in fish samples of high consumption in Spain and Portugal.

Mercury (Hg) and selenium (Se) determinations were carried out to evaluate human exposure to those elements through fish consumption in Spain and Portugal. Atomic fluorescence spectroscopy (AFS) was applied in a cold vapor mode for total mercury quantification and was also hyphenated to gas chromatography (GC) to achieve the speciation of organomercurial species in fish samples. The results obtained show the highest concentration of Hg in swordfish and tuna (0.47+/-0.02 and 0.31+/-0.01 microg g-1, respectively), and a much lower concentration in sardine, mackerel shad, and octopus (0.048+/-0.002, 0.033+/-0.001, and 0.024+/-0.001 microg g-1, respectively). The determination of alkyl mercury compounds revealed that 93-98% of mercury in the fish samples was in the organic form. Methylmercury (MeHg) was the only species found in the three fish species with higher mercury content. Total selenium concentration was high in sardine, swordfish, and tuna (0.43+/-0.02, 0.47+/-0.02, and 0.92+/-0.01 microg g-1, respectively), but low in mackerel shad and octopus (0.26+/-0.01 and 0.13+/-0.01 microg g-1, respectively). Speciation of selenium compounds was done by high-performance liquid chromatography in conjunction with inductively coupled plasma mass spectrometry (LC-ICP-MS). Selenomethionine (SeMet) was the only selenium compound identified in the fish samples with higher selenium content. Among the fish species studied, sardine had the most favourable Se:Hg and SeMet:MeHg molar ratios; therefore, its consumption seems to be preferable.

Animals↗
PubMed1991

Effects of selenium supplementation on blood and urine selenium levels and liver function in patients with primary biliary cirrhosis.

To study the mechanism of the reduced serum selenium concentration in patients with liver damage we administered 200 micrograms (2.53 mumol) selenium daily as selenium-rich yeast to 8 patients with primary biliary cirrhosis and 8 healthy controls over 16 weeks. Initially selenium concentrations in serum were 24% lower (P less than 0.001) in patients than controls. During supplementation serum selenium levels increased in both groups but the difference between them persisted. Throughout the study whole blood selenium levels and glutathione peroxidase activities were also somewhat lower (P = NS) in patients than controls. Selenium supplementation had no effect on whole blood glutathione peroxidase activities in either group. The basal 24 h urinary excretion of selenium was similar in both groups but was increased more by supplementation in patients than controls. Selenium administration did not influence the liver function of the patients. We conclude that impaired hepatic production of selenium-containing serum compounds is the most likely explanation for the reduced serum selenium concentration in patients with primary biliary cirrhosis.

Adult↗
PubMed2006

Consequences of vapor enhancement on selenium speciation analysis by HPLC/ICPMS.

Recent work has shown the presence of volatile selenium metabolites in human urine and suggested that these compounds could compromise quantitative selenium analyses by ICPMS. We show that with a commonly used sample introduction system (pneumatic nebulizer and spray chamber), two volatile selenium species recently identified in urine, namely, dimethyl selenide and dimethyl diselenide, gave greatly increased ICPMS responses (up to 58-fold) relative to selenite, an effect related to their volatilization in the spray chamber resulting in enhanced transport to the plasma. The quantitative consequences of this effect were demonstrated by measurement of total selenium and selenium species in certified reference material, NIES CRM 18 human urine. Direct flow injection analysis of the urine gave a total selenium concentration more than 2-fold higher than the certified value. These data suggested that NIES CRM 18 may contain part of its selenium as volatile species, and subsequent reversed-phase HPLC/ICPMS showed the presence of dimethyl selenide in addition to selenosugars and trimethylselenonium ion. Although the practice of quantifying unidentified chromatographic peaks against those of known compounds is common in speciation analysis, this approach when applied to NIES CRM 18 gave a value for the sum of selenium species which was twice the certified total selenium concentration. This work shows that the presence of volatile selenium species in urine precludes the use of flow injection analysis for total selenium measurements and imposes severe restrictions on the quantification of urinary selenium metabolites. In addition, it raises broader issues of the validity of the "dilute and shoot" approach to the determination of metals in clinical analysis of biological fluids.

Chromatography, High Pressure Liquid↗
PubMed2003

The effect of the presence of volatile organoselenium compounds on the determination of inorganic selenium by hydride generation.

As a result of microbiological activity it is possible to find dimethylselenium (DMSe) and dimethyldiselenium (DMDSe) in a wide type of environmental samples, such as soils, sediments, sewage sludges and plants where methylation can take place. Selenium determination by hydride-generation (HG) techniques requires its presence as Se(IV). Consequently, inorganic speciation by hydride generation techniques is done by first determining Se(IV) and then, after reduction of Se (VI) to Se(IV), the total selenium. Therefore, the concentration of Se (VI) is evaluated as the difference between total inorganic selenium and Se(IV). In the present work it could be demonstrated that DMSe and DMDSe are forming other volatile species by reaction with sodium borohydride, applying the same reduction condition as for inorganic selenium. These species are subsequently detected by several atomic techniques (atomic absorption AAS, atomic fluorescence AFS and inductively coupled plasma-mass spectrometry ICP-MS). The error that their presence can cause in determination of inorganic selenium has been evaluated. The magnitude of this error depends on the specific analytical detector used.The coupling of pervaporation-atomic fluorescence is proposed for the identification of these species and pervaporation-gas chromatography-atomic fluorescence for their individual quantification.

Journal Article↗
PubMed1992

Comparison of selenium and sulfur analogs in cancer prevention.

Several organoselenium compounds have been shown to have powerful anticarcinogenic activity. In view of certain similarities between selenium and sulfur biochemistry, we have evaluated the chemopreventive efficacy of three pairs of analogs using the 7,12-dimethylbenz[a]anthracene (DMBA)-induced mammary tumor model in rats. The compounds tested were selenocystamine/cysteamine, Semethylselenocysteine/S-methylcysteine, selenobetaine/sulfobetaine. In the first study, each agent was added to the basal AIN-76A diet and was given before and continued after DMBA treatment until the end. All three selenium compounds were active; a 50% inhibition was achieved at approximately 25 x 10(-6) mol/kg with Se-methylselenocysteine and selenobetaine and at approximately 40 x 10(-6) mol/kg with selenocystamine. In the sulfur series, only cysteamine and S-methylcysteine produced anticancer activity, and the levels required for comparable responses were 500- to 750-fold higher compared to the corresponding selenium analogs. Sulfobetaine was inactive even when present at near maximally tolerated levels. In the second study, Se-methylselenocysteine and S-methylcysteine were chosen for further examination during the initiation and post-initiation phases of mammary carcinogenesis. Se-Methylselenocysteine was effective when it was given either before or after DMBA administration. In contrast, S-methylcysteine was effective only after DMBA treatment. Thus, compared to the sulfur structural analogs, selenium compounds are much more active in cancer protection and may have a multi-modal mechanism in preventing cellular transformation as well as in delaying or inhibiting the expression of malignancy after carcinogen exposure.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed1998

Enhancement of selenium excretion in bile by sulfobromophthalein: elucidation of the mechanism.

This work was intended to explore the mechanism whereby sulfobromophthalein (BSP), an electrophilic and cholephilic organic acid, increases the biliary excretion of selenium in rats injected with sodium [75Se]selenite. In such animals, neither BSP-glutathione conjugate nor dibromosulfophthalein, nonelectrophilic congeners of BSP, enhanced the hepatobiliary transport of selenium, suggesting that reaction of nucleophilic selenite metabolites formed in vivo with the injected BSP may be involved. Indeed, HPLC analysis of bile from rats receiving [75Se]selenite and BSP revealed two peaks (X and Y) that were simultaneously detected both by absorbance as BSP metabolites and by radioactivity as [75Se] metabolites, indicating that these represent selenium-containing BSP metabolites. Pretreatment of rats with inhibitors of selenium methylation, such as periodate-oxidized adenosine (PAD) and ethionine, drastically diminished the size of peak X, while increasing (PAD) or not influencing (ethionine) the size of peak Y. This finding indicates that production of metabolite X, but not Y, is dependent on formation of methylated selenium metabolites. A compound chromatographically indistinguishable from that in peak X was formed in vitro during incubation of BSP with methylselenol, suggesting that biliary metabolite X is identical to the reaction product of BSP and selenite-derived methylselenol. Incubation of BSP with selenite in the presence of a thiol, namely glutathione, cysteine or N-acetylcysteine (which convert selenite into nucleophilic products, i.e. the respective selenopersulfides and hydrogen selenide) resulted in product(s) chromatographically identical to the biliary selenium-containing BSP metabolite(s) of peak Y, irrespective of the nature of the thiol used. Thus, biliary metabolite(s) Y may be reaction products of BSP and hydrogen selenide. Finally, BSP significantly diminished exhalation of dimethyl selenide in selenite-injected rats, purportedly because it reacted with precursors of dimethyl selenide, that include hydrogen selenide and methylselenol. In summary, BSP increases biliary excretion of selenium in rats receiving selenite because it forms selenium-containing BSP metabolites that are readily transported into bile. It is suggested that the in vivo reaction of nucleophilic selenite metabolites with electrophilic compounds may influence the fate of selenium and may contribute to some of the effects of this essential and anticarcinogenic metalloid.

Animals↗
PubMed1997

Observations on the efficacy of various forms of selenium for livestock: a review.

Since 1957, selenium has found extensive use in livestock production to maintain an adequate selenium status in animals in areas of soil and feed/forage deficiency. Selenium may be given directly to livestock, or applied as a fertilizer amendment to increase selenium content of their feeds. This paper addresses the area of direct supplementation, which includes oral and parenteral supplementation, and with ruminant animals the use of slow-release boluses. Various chemical forms of selenium have been examined as supplemental sources, with sodium selenite being the earliest compound of choice. Combination of selenium supplementation with other livestock management practices led to use of selenium dioxide, which avoided solubility problems with selenite but produced effective responses. Barium salts have been used with some success as supplemental selenium sources. Experience with ruminal boluses has shown that high pressure pelleting of increased grain size selenium, in hollow pellets, has prolonged their useful life. Attention has been paid recently to residual selenium returned to the soil from livestock supplementation practices and the resulting opinion is that currently approved practices are acceptable from the point of view of environmental quality.

Animal Feed↗
PubMed2006

Selenoprotein expression is regulated at multiple levels in prostate cells.

Selenium supplementation in a population with low basal blood selenium levels has been reported to decrease the incidence of several cancers including prostate cancer. Based on the clinical findings, it is likely that the antioxidant function of one or more selenoproteins is responsible for the chemopreventive effect, although low molecular weight seleno-compounds have also been posited to selectively induce apoptosis in transformed cells. To address the effects of selenium supplementation on selenoprotein expression in prostate cells, we have undertaken an analysis of antioxidant selenoprotein expression as well as selenium toxicity in non-tumorigenic prostate epithelial cells (RWPE-1) and prostate cancer cells (LNCaP and PC-3). Our results show that two of the glutathione peroxidase family members (GPX1 and GPX4) are highly induced by supplemental selenium in prostate cancer cells but only slightly induced in RWPE-1 cells. In addition, GPX1 levels are dramatically lower in PC-3 cells as compared to RWPE-1 or LNCaP cells. GPX2 protein and mRNA, however, are only detectable in RWPE-1 cells. Of the three selenium compounds tested (sodium selenite, sodium selenate and selenomethionine), only sodium selenite shows toxicity in a physiological range of selenium concentrations. Notably and in contrast to previous studies, RWPE-1 cells were significantly more sensitive to selenite than either of the prostate cancer cell lines. These results demonstrate that selenoproteins and selenium metabolism are regulated at multiple levels in prostate cells.

Cell Line, Tumor↗
PubMed1977

[Studies of the tolerance and toxicity of Luzern-green-meal pellets after selenium fertilization].

In a feeding trial, rabbits allotted in 3 experimental groups were fed rations containing 2.09, 9.83 and 19.5 mg selenium/kg feed in the form of selenium-enriched alfalfa green meal pellets. The selenium enrichment was done by foliar application (spraying) of the 20--25 cm high plant stand with 2.5 kg SeO2 per hectare in watery solution. The control animals were given normal alfalfa green meal pellets of 0.16 ppm selenium content. Toxicity and lethality, tolerance limit and nutritive effect of the pellets were studied. Plant-assimilated selenium was found to be converted more efficiently by the animal organism than was selenium from inorganic compounds (higher retention rate, better gain in body weight and lower feed expenditure). Therefore, the selenium supply to farm animals should be improved by feeding crops that were given selenium dressings.

Animal Feed↗