Development of a hydrolysis-based small-molecule hydrogen selenide (H<sub>2</sub>Se) donor

Newton, Turner D.; Pluth, Michael D.

doi:10.1039/c9sc04616j

Cited by 21 publications

(25 citation statements)

References 35 publications

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“…S22 †). 25 The color change of NBD-S8 solution and MBA tests of the solution clearly suggested NBD-S8 could efficiently scavenge H 2 S when the H 2 S-containing gas was passed through the NBD-S8 solution.…”

Section: Resultsmentioning

confidence: 94%

Highly efficient H₂S scavengers via thiolysis of positively-charged NBD amines

et al. 2020

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Section: Resultsmentioning

confidence: 94%

Highly efficient H₂S scavengers via thiolysis of positively-charged NBD amines

et al. 2020

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), natural abundance (7.63%), no quadrupolar moment, magnetogyric ratio (5.12×10 7 rad.s −1 .T −1 ) and negligible nuclear Overhauser effect (nOe) [60]…”

Section: Se Nmr Spectroscopy In Organic Synthesismentioning

confidence: 99%

“…Selenium element has proven to be a suitable nuclide in NMR spectroscopy in studies on stability, [40] reactivity, [41,42] chirality, [43,44,45,46,47,48] polymers, [49,50,51] coordination chemistry, [52,53,54,55] and bio-based experiments. [56,57,58,59] The great potential of 77 Se NMR experiments can be attributed to selenium-77 isotope properties, as spin ( 1 = 2 ), natural abundance (7.63%), no quadrupolar moment, magnetogyric ratio (5.12 × 10 7 rad.s À 1 .T À 1 ) and negligible nuclear Overhauser effect (nOe). [60] The wide spectral window of selenium-77 isotope (δ Se = À 700 to + 2200 ppm) provides an accurate form to identify and quantify organoselenium compounds, which the Figure 1 illustrates the resonance ranges of various selenium organic functions.…”

Section: Se Nmr Spectroscopy In Organic Synthesismentioning

confidence: 99%

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

et al. 2020

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This review article deals with organic synthesis from the perspective of selenium-77 nuclear magnetic resonance (NMR) spectroscopy. Different types of organic reactions are briefly discussed, incorporating mechanism aspects through 77 Se NMR observable intermediates and byproducts. The 77 Se NMR experiments are demonstrated in terms of structural characterization and new insights for organic reactions. The ability to visualize different molecules in a reaction mixture provides a facile and versatile route for the development of synthetic organoselenium compounds. Thus, the review describes the strategies accomplished mainly in the past five years in the syntheses and applications of the organoselenium compounds, focusing on 77 Se NMR spectroscopy.

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“…SeMet can be trans-selenated to SeCys, which is then converted to H 2 Se by SeCys β-lyase [ 4 ]. On the other hand, sodium selenite reduces to H 2 Se through interaction with glutathione (GSH), producing selenodiglutathione (GSSeSG), which is further metabolised by GSH reductase into glutathioselenol (GSSeH), GSSeH either decomposes to GSH and Se 0 or is converted to H 2 Se through enzymatic and non-enzymatic pathways [ 10 ]. H 2 Se is then converted to selenophosphate (HSePO 3 2− ) for downstream incorporation into selenoproteins such as GPx, or excretion in urine as a selenosugar [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Analysis of Bioavailability and Induction of Glutathione Peroxidase by Dietary Nanoelemental, Organic and Inorganic Selenium

et al. 2021

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Dietary organic selenium (Se) is commonly utilized to increase formation of selenoproteins, including the major antioxidant protein, glutathione peroxidase (GPx). Inorganic Se salts, such as sodium selenite, are also incorporated into selenoproteins, and there is evidence that nanoelemental Se added to the diet may also be effective. We conducted two trials, the first investigated inorganic Se (selenite), organic Se (L-selenomethionine) and nanoelemental Se, in conventional mice. Their bioavailability and effectiveness to increase GPx activity were examined. The second trial focused on determining the mechanism by which dietary Se is incorporated into tissue, utilising both conventional and germ-free (GF) mice. Mice were fed a diet with minimal Se, 0.018 parts per million (ppm), and diets with Se supplementation, to achieve 0.07, 0.15, 0.3 and 1.7 ppm Se, for 5 weeks (first trial). Mass spectrometry, Western blotting and enzymatic assays were used to investigate bioavailability, protein levels and GPx activity in fresh frozen tissue (liver, ileum, plasma, muscle and feces) from the Se fed animals. Inorganic, organic and nanoelemental Se were all effectively incorporated into tissues. The high Se diet (1.7 ppm) resulted in the highest Se levels in all tissues and plasma, independent of the Se source. Interestingly, despite being ~11 to ~25 times less concentrated than the high Se, the lower Se diets (0.07; 0.15) resulted in comparably high Se levels in liver, ileum and plasma for all Se sources. GPx protein levels and enzyme activity were significantly increased by each diet, relative to control. We hypothesised that bacteria may be a vector for the conversion of nanoelemental Se, perhaps in exchange for S in sulphate metabolising bacteria. We therefore investigated Se incorporation from low sulphate diets and in GF mice. All forms of selenium were bioavailable and similarly significantly increased the antioxidant capability of GPx in the intestine and liver of GF mice and mice with sulphate free diets. Se from nanoelemental Se resulted in similar tissue levels to inorganic and organic sources in germ free mice. Thus, endogenous mechanisms, not dependent on bacteria, reduce nanoelemental Se to the metabolite selenide that is then converted to selenophosphate, synthesised to selenocysteine, and incorporated into selenoproteins. In particular, the similar efficacy of nanoelemental Se in comparison to organic Se in both trials is important in the view of the currently limited cheap sources of Se.

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Development of a hydrolysis-based small-molecule hydrogen selenide (H₂Se) donor

Abstract: Hydrolysis-based H2Se donors provide new chemical tools for investigating biological H2Se.

Cited by 21 publications

References 35 publications

Highly efficient H₂S scavengers via thiolysis of positively-charged NBD amines

Highly efficient H₂S scavengers via thiolysis of positively-charged NBD amines

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

Analysis of Bioavailability and Induction of Glutathione Peroxidase by Dietary Nanoelemental, Organic and Inorganic Selenium

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Development of a hydrolysis-based small-molecule hydrogen selenide (H2Se) donor

Abstract: Hydrolysis-based H2Se donors provide new chemical tools for investigating biological H2Se.

Cited by 21 publications

References 35 publications

Highly efficient H2S scavengers via thiolysis of positively-charged NBD amines

Highly efficient H2S scavengers via thiolysis of positively-charged NBD amines

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

Analysis of Bioavailability and Induction of Glutathione Peroxidase by Dietary Nanoelemental, Organic and Inorganic Selenium

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Resources

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Development of a hydrolysis-based small-molecule hydrogen selenide (H₂Se) donor

Highly efficient H₂S scavengers via thiolysis of positively-charged NBD amines

Highly efficient H₂S scavengers via thiolysis of positively-charged NBD amines