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PubMed2004

Identification of non-peptide species in selenized yeast by MALDI mass spectrometry using post-source decay and orthogonal Q-TOF detection.

The potential of tandem mass spectrometry following matrix-assisted laser desorption ionization (MALDI) was studied for speciation of selenium. Non-peptide selenium-containing compounds were isolated from a selenized yeast aqueous extract by size-exclusion chromatography. Post-source decay (PSD) was compared with orthogonal quadrupole collision cell dissociation for the purpose of obtaining fragmentation and structural information. In the PSD mode, the use of ion gate covering the whole isotopic cluster of the parent compound allowed the immediate recognition of fragments containing Se and those in which this element was absent. The tandem mass spectra obtained by orthogonal MALDI Q-TOF were equally informative in terms of the number of fragments but suffered from a poorer sensitivity. The mass accuracy was ca. 20 times better in the oMALDI configuration than in the PSD mode. An unknown selenium compound with an m/z 388 was detected with a mass accuracy of 3 ppm according to the proposed empiric formula.

Selenium↗
PubMed1997

Antifungal, antibacterial, antiviral and cytotoxic activity of novel thio- and seleno-azoles.

A series of pentaatomic heterocyclic compounds containing sulphur or selenium in position 2, were tested for cytotoxicity, antiviral and antimicrobial activities. Generally, selenium-containing compounds were more toxic than the corresponding sulphur-containing ones (30-75 times more toxic) and, furthermore, the biological activity against some microorganisms was also enhanced. In particular, some selenium-containing derivatives exerted an inhibitory activity on plant pathogenic fungi at doses markedly lower than the toxic ones, showing an interesting selectivity of action. In this case the tested compounds appeared more active than ketoconazole, the control used, with an almost comparable degree of cytotoxicity.

Animals↗
PubMed1988

Hybridoma cultivation in defined serum-free media: growth-supporting substances. V. Trace elements.

The effects of selenium and manganese on growth of hybridomas in serum-free medium were studied. The optimum growth-supporting concentration of Na2SeO3 was about 50 nM. Omission of selenite resulted in decreased growth (60-70% of the number of cells growing with selenite when cultivated for 3 days). The optimum growth-supporting concentration of MnCl2 was 0.5 nM. The number of hybridoma cells growing 3 days without MnCl2 represented about 80% of the cell number obtained by cultivation with MnCl2. Compounds of other trace elements did not display growth-stimulating activity, when tested in short-term culture, perhaps with the exception of lithium at relatively very high concentrations (about 0.2-0.6 mM).

Animals↗
PubMedDate not supplied

The reaction of ebselen with peroxynitrite.

Ebselen, 2-phenyl-1,2-benzisoselenazol-3(2H)-one, rapidly reacts with peroxynitrite, the rate constant being of the order of 10(6) M-1 s-1; the reaction yields the selenoxide of the parent molecule, 2-phenyl-1,2-benzisoselenazol-3(2H)-one 1-oxide, as the sole selenium-containing product; a stoichiometry of 1 mol of ebselen reacted and of the selenoxide formed per mole of peroxynitrite was observed. The reaction was studied in detail at neutral and alkaline pH (pH 10-11). It also proceeds at acidic pH where peroxynitrous acid (ONOOH) is predominant, the yield of the selenoxide being lower because peroxynitrous acid (pKa = 6.8) decays rapidly. Reduction of the selenoxide in cells to regenerate ebselen would allow for a sustained defense against peroxynitrite. This novel reaction constitutes a potential cellular defense line against peroxynitrite, one of the important reactive species in inflammatory processes.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed1999

Selenophosphate as a substrate for mammalian selenocysteine synthase, its stability and toxicity.

The mechanism of selenocysteine synthesis on tRNASec in mammals was previously studied by means of HSe- as a Se donor to synthesize selenocysteine. It has been recently established that HSe- in E. coli is activated by ATP to become selenophosphate (SeP). In this study, we provide evidence that [75Se]selenocysteine is produced by bovine selenocysteine synthase from Ser-tRNASec and [75Se]Sep, synthesized from elemental 75Se and Tris(trimethylsilyl)phosphite. We also studied the stability of SeP by NMR measurement. SeP was stable during storage under nitrogen at -80 degrees C for 3 months in 0.2 M Hepes buffer at pH 6.8. However, SeP decomposed at 0 degree C in air (half life 32 hrs) or at 22 degrees C under nitrogen (half life 30 hrs) at pH 6.8. The half lives of SeP at -19 degrees C in air and at 0 degree C under nitrogen at pH 6.8 were 740 and 840 hrs, respectively. At pH 4 under nitrogen at 22 degrees C, the half life was 240 hrs. The half life was only 9.2 hrs at pH 9 under nitrogen at 0 degree C. Thus, SeP was proved to be stable at low temperature, under acidic and anaerobic conditions, but labile under neutral and alkaline conditions. The LD50 of SeP administered i.p. to mice was 37.5 mg/kg body weight.

Air↗
PubMed2007

Polymeric organometallic architectures of novel P-Se anions.

The characterisation of a series of compounds obtained from Woollins' reagent (W.R.) offers a novel approach to organometallic coordination polymers. The syntheses were achieved by nucleophilic ring-opening reactions of W.R. with metal salts and crystallisation using solvent-diffusion techniques. One-dimensional coordination polymers are formed as a result, and we demonstrate that the dimensionality of the polymers can be influenced by using hydrated metal salts or by the construction of heterometallic arrangements.

Anions↗
PubMed1984

Synthesis of [75Se]trimethylselenonium iodide from [75Se]selenocystine.

The synthesis of [75Se]trimethylselenonium iodide from [75Se]selenocystine is described. The starting compound is reduced to [75Se]selenocysteine with borohydride and reacted with methyl iodide to form [75Se]Se-methyl-selenocysteine, then treated with methyl iodide in formic acid solution to form Se-dimethyl-selenocysteine selenonium iodide. Over a period of days, the selenonium intermediate undergoes spontaneous elimination to form alanine and dimethyl selenide, which reacts with methyl iodide to give the trimethylselenonium product in over 90% yield.

Borohydrides↗
PubMed2006

Trigonal bipyramidal iron(III) and manganese(III) oxo, sulfido, and selenido complexes. An electronic-structural overview.

Using density functional theory calculations, we have carried out a broad survey of trigonal bipyramidal iron(III) and manganese(III) oxo, sulfido, selenido, and hydroxo complexes, with tripodal tetradentate "triureidoamine" supporting ligands. The calculations reproduce the experimentally observed high-spin states of these compounds; a multifunctional analysis suggests that the high-spin nature of these species follows largely from their trigonal bipyramidal geometry. In conjunction with earlier calculations, the present study provides a broad overview of spin density profiles in iron-oxo species in general. Iron-oxo d(pi)-p(pi) interactions invariably result in a substantial spin density on the oxygen, which in turn may be significantly tuned by hydrogen bonding interactions. The oxygen spin densities are smaller in analogous manganese-oxo species, indicating that manganese is less adept at pi-bonding than iron, which parallels earlier findings on porphyrin systems. The Fe(III)-S/Se spin density profiles provide one of the first confirmations in a transition metal context of Schleyer's prediction that the heavier p-block elements are as effective as their second-row congeners in terms of their pi-donating ability.

Ferric Compounds↗
PubMed2003

Synthesis of a molecular Mo2Fe6S9 cluster with the topology of the PN cluster of nitrogenase by rearrangement of an edge-bridged Mo2Fe6S8 double cubane.

The structures of the P cluster and cofactor cluster of nitrogenase are well-defined crystallographically. They have been obtained only by biosynthesis; their chemical synthesis remains a challenge. Synthetic routes are sought to the P cluster in the P(N) state in which two cuboidal Fe(3)S(3) units are connected by a mu(6)-S atom and two Fe-(mu(2)-S(Cys))-Fe bridges. A reaction scheme affording a Mo(2)Fe(6)S(9) cluster in molecular form having the topology of the P(N) cluster has been devised. Reaction of the single cubane [(Tp)MoFe(3)S(4)Cl(3)](1)(-) with PEt(3) gives [(Tp)MoFe(3)S(4)(PEt(3))(3)](1+) (2), which upon reduction with BH(4)(-) affords the edge-bridged all-ferrous double cubane [(Tp)(2)Mo(2)Fe(6)S(8)(PEt(3))(4)] (4) (Tp = tris(pyrazolylhydroborate(1-)). Treatment of 4 with 3 equiv of HS(-) produces [(Tp)(2)Mo(2)Fe(6)S(9)(SH)(2)](3)(-) (7) as the Et(4)N(+) salt in 86% yield. The structure of 7 is built of two (Tp)MoFe(3)(mu(3)-S)(3) cuboidal fragments bridged by two mu(2)-S atoms and one mu(6)-S atom in an arrangement of idealized C(2) symmetry. The cluster undergoes three one-electron oxidation reactions and is oxidatively cleaved by p-tolylthiol to [(Tp)MoFe(3)S(4)(S-p-tol)(3)](2)(-) and by weak acids to [(Tp)MoFe(3)S(4)(SH)(3)](2-). The cluster core of 7 has the bridging pattern [Mo(2)Fe(6)(mu(2)-S)(2)(mu(3)-S)(6)(mu(6)-S)](1+) with the probable charge distribution [Mo(3+)(2)Fe(2+)(5)Fe(3+)S(9)](1+). Cluster 7 is a topological analogue of the P(N) cluster but differs in having two heteroatoms and two Fe-(mu(2)-S)-Fe instead of two Fe-(mu(2)-S(Cys))-Fe bridges. A best-fit superposition of the two cluster cores affords a weighted rms deviation in atom positions of 0.38 A. Cluster 7 is the first molecular topological analogue of the P(N) cluster. This structure had been prepared previously only as a fragment of complex high-nuclearity Mo-Fe-S clusters.

Biomimetic Materials↗
PubMed2004

Enzymatic synthesis of phosphoroselenoate DNA using thymidine 5'-(alpha-P-seleno)triphosphate and DNA polymerase for X-ray crystallography via MAD.

We report here the first study of enzymatic synthesis of two phosphoroselenoate (PSe) DNAs using the two alpha-Se-TTP diastereomers (Sp and Rp) and DNA polymerase. The experimental results indicate that Klenow equally recognizes the two individual diastereomers at the same level as natural TTP. The incorporations of the PSe groups at the expected sites have been confirmed by the digestion resistance to exonuclease III, and the different patterns of the digestion resistance of DNA I and II indicate the configurational differences of the PSe centers (Sp or Rp). Unlike chemical synthesis, which is limited to short DNAs and where the separation of the PSe DNA diastereomers is necessary, this enzymatic method can be used to prepare longer DNAs without diastereomer separation. This quantitative enzymatic approach is particular valuable for the synthesis of longer DNAs with multiple PSe groups in large scale for their X-ray crystal structure determination by the MAD phasing technique.

Crystallography, X-Ray↗
PubMed2006

Hydrogen-deuterium exchange between TpRu(PMe3)(L)X (L = PMe3 and X = OH, OPh, Me, Ph, or NHPh; L = NCMe and X = Ph) and deuterated arene solvents: evidence for metal-mediated processes.

At elevated temperatures (90-130 degrees C), complexes of the type TpRu(PMe3)2X (X = OH, OPh, Me, Ph, or NHPh; Tp = hydridotris(pyrazolyl)borate) undergo regioselective hydrogen-deuterium (H/D) exchange with deuterated arenes. For X = OH or NHPh, H/D exchange occurs at hydroxide and anilido ligands, respectively. For X = OH, OPh, Me, Ph, or NHPh, isotopic exchange occurs at the Tp 4-positions with only minimal deuterium incorporation at the Tp 3- or 5-positions or PMe3 ligands. For TpRu(PMe3)(NCMe)Ph, the H/D exchange occurs at 60 degrees C at all three Tp positions and the phenyl ring. TpRu(PMe3)2Cl, TpRu(PMe3)2OTf (OTf = trifluoromethanesulfonate), and TpRu(PMe3)2SH do not initiate H/D exchange in C6D6 after extended periods of time at elevated temperatures. Mechanistic studies indicate that the likely pathway for the H/D exchange involves ligand dissociation (PMe3 or NCMe), Ru-mediated activation of an aromatic C-D bond, and deuteration of basic nondative ligand (hydroxide or anilido) or Tp positions via net D+ transfer.

Cadmium Compounds↗
PubMed2004

Nanocluster magic.

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Cadmium Compounds↗
PubMed2005

Colloidal CdSe nanocrystals from tri-n-octylphosphine: Part 1: growth and optical properties from polar and non-polar solvents.

This manuscript reports the ready synthesis of high-quality colloidal CdSe nanocrystals from tri-n-octylphosphine (TOP) and reports the optical properties of the resulting CdSe dispersed in nonpolar and polar environments. With cadmium oxide (CdO) as the Cd precursor and TOPSe as the Se source, the CdSe nanocrystals were synthesized in a reaction medium consisting of TOP. The synthetic approach is as simple as: the swift injection of a TOPSe/TOP solution into a CdO/TOP solution at one particular (high) temperature, with subsequent growth at a lower temperature. The temporal evolution of the optical properties, including absorption and luminescence, were monitored in detail. The photoluminescence (PL) properties of the TOP-capped CdSe investigated comprise the intensity, emission peak wavelength, full width at half maximum of the PL spectra, and stability; these PL properties are sensitive to the history of growth as well as the environment of dispersion. An appropriate parameter, termed "Sensitivity Index (SI)," is proposed to define the percent difference in the PL intensity that arises when the dots are dispersed in non-polar hexane (Hex) as compared to polar tetrahydrofuran (THF). The decrease in the PL efficiency on going from Hex to THF is attributed to changes in surface states rather than in the internal core as more ligands are removed in THF. Dilution experiments further confirm the suggestion of the ligand removal mechanism and provide a conceptual estimate of surface quality via the SI parameter. Due to a slow growth in size (the size of the nanocrystals is almost constant during early 20 min) and good PL stability (tested as PL changes after storage for days both in dispersed or solid states, as well as after UV-irradiation), we suggest that our synthetic approach is likely to be practical for large-scale CdSe nanocrystals with good PL stability.

Cadmium↗
PubMed2005

Colloidal CdSe nanocrystals from tri-n-octylphosphine: Part II: control of growth rate for high quality and large-scale production by tuning Cd-to-Se stoichiometry.

Colloidal CdSe nanocrystals were synthesized in reaction media consisting of tri-n-octylphosphine (TOP) without addition of other species; the single-step approach used cadmium oxide (CdO) and TOPSe as Cd and Se sources, respectively. The temporal evolution of the optical properties of the growing TOP-capped CdSe nanocrystals was monitored for a couple of hours, showing that there are two distinguishable stages of growth: an early stage (less than 5 minutes) and a later stage; the growth kinetics of the two stages is a function of the Cd-to-Se precursor molar ratios. A rational choice of 2-6Cd-to-1Se molar ratio was found, based on the temporal evolution of the photoluminescent (PL) efficiency (studied as PL intensity and sensitivity to the media of dispersion, and non-resonant Stokes shifts). For a 2Cd-to-1Se synthesis, the growth in size was slow in the early stages and became fast in the later stages; this fast-later-stage feature could be suppressed by going to a synthesis with a 4-6Cd-to-1Se mole ratio: the nanocrystals between 0.5-60 min growth time exhibit very much similar optical properties, with less than 19 nm redshift of bandgap absorption and emission occurring. Thus, the synthetic route developed here, with a rational 4-6Cd-to-1Se molar ratio, enables us to produce high-quality CdSe nanocrystals on a large-scale with a high degree of synthetic reproducibility. The insights gained facilitate a deeper understanding of the concept of what constitutes high-quality nano-crystals: high PL efficiency resulting from a low growth rate, which can be thoroughly and readily investigated by the red-shift rate of the band-gap peak positions; in addition, the insights gained help us to define a proper synthetic approach for large-scale production with high-quality product.

Cadmium↗