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Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 April 2017) | Viewed by 118600

Special Issue Editors

Prof. Dr. Claudio Santi

E-Mail Website
Guest Editor
Group of Catalysis and Organic Grenn Chemistry, Department of Pharmaceutical Sciences, University of Perugia, 06123 Perugia, PG, Italy
Interests: selenium; catalysis; green chemistry; flow chemistry; synthetic methodologies; redox; complexity
Special Issues, Collections and Topics in MDPI journals
Dr. Luana Bagnoli

E-Mail Website
Assistant Guest Editor
Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, 06123 Perugia, Italy
Interests: organic synthesis; organoselenium compounds; heterocycles; multibond-forming reactions; drug-like molecules; environmentally friendly synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

In 2017, we will celebrate 200 years of research on selenium. In 1817, the Swedish chemists, Berzelius and Gahn, on roasting 200 kg of sulfur from a pyrite from the Falun mine, obtained about 3 g of a precipitate that they first wrongly identified as tellurium. Berzelius doubted this result and repeated the analysis some months later. He then realized that a new element was identified and he named this element Selenium (Greek: selene, moon) in consideration of its resemblance to tellurium (Latin: tellus, earth). Nowadays selenium containing compounds, capitalizing on two centuries of research and developments, play an important role in organic synthesis and biology. In particular, the redox properties of this element were studied and investigated from a synthetical point of view, as well as in consideration of its crucial involvement in several important biological processes. Organoselenium reagents can be efficiently used in selective electrophilic, nucleophilic and radical reactions such as stoichiometric reactants, or as catalysts showing, in this latter case, an appreciable TOF with respect to other analogue organocatalysts. Furthermore, modern application in medicinal chemistry, green chemistry, and chemistry of new materials are forming a new golden age for this element in the present and the near future.

This Special Issue welcomes the submission of papers based on original research that describe selenium compounds and their applications ranging from synthetically relevant organic transformations to the design and development of new selenium containing biologically active compounds and functionalized and smart materials.

Historical reviews as well as prospective analyses for the future in this field of research will be taken into consideration.

Prof. Dr. Claudio Santi
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • selenium
  • electrophile
  • nucleophile
  • radical
  • redox
  • stereoselectivity
  • selenoproteins

Published Papers (17 papers)

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Editorial

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188 KiB  
Editorial
Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospective
by Claudio Santi and Luana Bagnoli
Molecules 2017, 22(12), 2124; https://doi.org/10.3390/molecules22122124 - 02 Dec 2017
Cited by 27 | Viewed by 4765
Abstract
In 2017, the 200th anniversary of the discovery of selenium was celebrated. In 1817, the Swedish chemists, Berzelius and Gahn, on roasting 200 kg of sulfur from a pyrite from the Falun mine, obtained about 3 g of a precipitate that they first [...] Read more.
In 2017, the 200th anniversary of the discovery of selenium was celebrated. In 1817, the Swedish chemists, Berzelius and Gahn, on roasting 200 kg of sulfur from a pyrite from the Falun mine, obtained about 3 g of a precipitate that they first wrongly identified as tellurium. Berzelius doubted this result and repeated the analysis some months later realizing that a new element was in his hands and he named this element Selenium (Greek: Selene, moon) in consideration of its resemblance to Tellurium (Latin: Tellus, earth). Several events were organized in the year for this special celebration and this Special Issue would like to be an additional contribution to the success of a research that, especially during the last decades, rapidly grew in different fields: synthesis, medicinal chemistry, biology, material, and environment. These studies are strongly characterized by multi- and interdisciplinary connections, and, for this reason, we collected here contributions coming from different areas and disciplines, not exclusively synthetic organic chemistry. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)

Research

Jump to: Editorial, Review

1526 KiB  
Article
Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions
by Sumbal Saba, Giancarlo Vaccari Botteselle, Marcelo Godoi, Tiago Elias Allievi Frizon, Fábio Zazyki Galetto, Jamal Rafique and Antonio L. Braga
Molecules 2017, 22(8), 1367; https://doi.org/10.3390/molecules22081367 - 18 Aug 2017
Cited by 43 | Viewed by 6938
Abstract
The efficient and mild copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides under ligand- and solvent-free conditions is described. The cross-coupling reaction was performed using aryl boric acids and 0.5 equiv. of diorganyl dichalcogenides (Te/Se/S) in the presence of 3 mol % of CuI and [...] Read more.
The efficient and mild copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides under ligand- and solvent-free conditions is described. The cross-coupling reaction was performed using aryl boric acids and 0.5 equiv. of diorganyl dichalcogenides (Te/Se/S) in the presence of 3 mol % of CuI and 3 equiv. of DMSO, under microwave irradiation. This new protocol allowed the preparation of several unsymmetrical diorganyl chalcogenides in good to excellent yields. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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487 KiB  
Article
Reaction of bis[(2-chlorocarbonyl)phenyl] Diselenide with Phenols, Aminophenols, and Other Amines towards Diphenyl Diselenides with Antimicrobial and Antiviral Properties
by Mirosław Giurg, Anna Gołąb, Jakub Suchodolski, Rafał Kaleta, Anna Krasowska, Egbert Piasecki and Magdalena Piętka-Ottlik
Molecules 2017, 22(6), 974; https://doi.org/10.3390/molecules22060974 - 12 Jun 2017
Cited by 33 | Viewed by 6007
Abstract
A reaction of bis[(2-chlorocarbonyl)phenyl] diselenide with various mono and bisnucleophiles such as aminophenols, phenols, and amines have been studied as a convenient general route to a series of new antimicrobial and antiviral diphenyl diselenides. The compounds, particularly bis[2-(hydroxyphenylcarbamoyl)]phenyl diselenides and reference benzisoselenazol-3(2H [...] Read more.
A reaction of bis[(2-chlorocarbonyl)phenyl] diselenide with various mono and bisnucleophiles such as aminophenols, phenols, and amines have been studied as a convenient general route to a series of new antimicrobial and antiviral diphenyl diselenides. The compounds, particularly bis[2-(hydroxyphenylcarbamoyl)]phenyl diselenides and reference benzisoselenazol-3(2H)-ones, exhibited high antimicrobial activity against Gram-positive bacterial species (Enterococcus spp., Staphylococcus spp.), and some compounds were also active against Gram-negative E. coli and fungi (Candida spp., A. niger). The majority of compounds demonstrated high activity against human herpes virus type 1 (HHV-1) and moderate activity against encephalomyocarditis virus (EMCV), while they were generally inactive against vesicular stomatitis virus (VSV). Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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4079 KiB  
Article
Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions
by Luca Sancineto, Jaqueline Pinto Vargas, Bonifacio Monti, Massimiliano Arca, Vito Lippolis, Gelson Perin, Eder Joao Lenardao and Claudio Santi
Molecules 2017, 22(6), 953; https://doi.org/10.3390/molecules22060953 - 08 Jun 2017
Cited by 16 | Viewed by 5305
Abstract
We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)2Zn] or [(PhSe)2Zn]TMEDA with acyl chlorides under “on water” conditions. The method is applicable to a series of aromatic and aliphatic [...] Read more.
We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)2Zn] or [(PhSe)2Zn]TMEDA with acyl chlorides under “on water” conditions. The method is applicable to a series of aromatic and aliphatic acyl chlorides and tolerates the presence of other functionalities in the starting material. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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2196 KiB  
Article
Selenium Speciation in the Fountain Creek Watershed (Colorado, USA) Correlates with Water Hardness, Ca and Mg Levels
by James S. Carsella, Irma Sánchez-Lombardo, Sandra J. Bonetti and Debbie C. Crans
Molecules 2017, 22(5), 708; https://doi.org/10.3390/molecules22050708 - 30 Apr 2017
Cited by 7 | Viewed by 5489
Abstract
The environmental levels of selenium (Se) are regulated and strictly enforced by the Environmental Protection Agency (EPA) because of the toxicity that Se can exert at high levels. However, speciation plays an important role in the overall toxicity of Se, and only when [...] Read more.
The environmental levels of selenium (Se) are regulated and strictly enforced by the Environmental Protection Agency (EPA) because of the toxicity that Se can exert at high levels. However, speciation plays an important role in the overall toxicity of Se, and only when speciation analysis has been conducted will a detailed understanding of the system be possible. In the following, we carried out the speciation analysis of the creek waters in three of the main tributaries—Upper Fountain Creek, Monument Creek and Lower Fountain Creek—located in the Fountain Creek Watershed (Colorado, USA). There are statistically significant differences between the Se, Ca and Mg, levels in each of the tributaries and seasonal swings in Se, Ca and Mg levels have been observed. There are also statistically significant differences between the Se levels when grouped by Pierre Shale type. These factors are considered when determining the forms of Se present and analyzing their chemistry using the reported thermodynamic relationships considering Ca2+, Mg2+, SeO42−, SeO32− and carbonates. This analysis demonstrated that the correlation between Se and water hardness can be explained in terms of formation of soluble CaSeO4. The speciation analysis demonstrated that for the Fountain Creek waters, the Ca2+ ion may be mainly responsible for the observed correlation with the Se level. Considering that the Mg2+ level is also correlating linearly with the Se levels it is important to recognize that without Mg2+ the Ca2+ would be significantly reduced. The major role of Mg2+ is thus to raise the Ca2+ levels despite the equilibria with carbonate and other anions that would otherwise decrease Ca2+ levels. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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2012 KiB  
Article
New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential
by Agata J. Pacuła, Katarzyna B. Kaczor, Jędrzej Antosiewicz, Anna Janecka, Angelika Długosz, Tomasz Janecki, Andrzej Wojtczak and Jacek Ścianowski
Molecules 2017, 22(3), 492; https://doi.org/10.3390/molecules22030492 - 20 Mar 2017
Cited by 38 | Viewed by 6976
Abstract
New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives [...] Read more.
New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives was evaluated and compared to the reactivity of a series of N-amino acid benzisoselenazol-3(2H)-ones obtained by a modified procedure involving the improved synthesis and isolation of the diseleno bis(dibenzoic) acid. The most efficient peroxide scavengers, N-bornyl and N-leucine methyl ester benzisoselenazol-3(2H)-ones, were further evaluated as cytotoxic agents on four cancer cell lines (MCF-7, HEP G2, HL 6, and DU 145) and normal cell line PNT1A. The highest antiproliferative potential was evaluated for two compounds bearing a 3-methylbutyl carbon chain, N-leucine methyl ester and N-3-methylbutyl benzisoselenazol-3(2H)-ones. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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5237 KiB  
Communication
Glycerol as Precursor of Organoselanyl and Organotellanyl Alkynes
by Eder J. Lenardão, Elton L. Borges, Guilherme Stach, Liane K. Soares, Diego Alves, Ricardo F. Schumacher, Luana Bagnoli, Francesca Marini and Gelson Perin
Molecules 2017, 22(3), 391; https://doi.org/10.3390/molecules22030391 - 02 Mar 2017
Cited by 6 | Viewed by 5076
Abstract
Herein we describe the synthesis of organoselanyl and organotellanyl alkynes by the addition of lithium alkynylchalcogenolate (Se and Te) to tosyl solketal, easily obtained from glycerol. The alkynylchalcogenolate anions were generated in situ and added to tosyl solketal in short reaction times, furnishing [...] Read more.
Herein we describe the synthesis of organoselanyl and organotellanyl alkynes by the addition of lithium alkynylchalcogenolate (Se and Te) to tosyl solketal, easily obtained from glycerol. The alkynylchalcogenolate anions were generated in situ and added to tosyl solketal in short reaction times, furnishing in all cases the respective products of substitution in good yields. Some of the prepared compounds were deprotected using an acidic resin to afford new water-soluble 3-organotellanylpropane-1,2-diols. The synthetic versatility of the new chalcogenyl alkynes was demonstrated in the iodocyclization of 2,2-dimethyl-1,3-dioxolanylmethyl(2-methoxyphenylethynyl)selane 3f, which afforded 3-iodo-2-(2,2-dimethyl-1,3-dioxolanylmethyl) selenanylbenzo[b]furan in 85% yield, opening a new way to access water-soluble Se-functionalized benzo[b]furanes. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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2959 KiB  
Article
Glutathione Peroxidase-Like Activity of Amino-Substituted Water-Soluble Cyclic Selenides: A Shift of the Major Catalytic Cycle in Methanol
by Kenta Arai, Ayako Tashiro, Yuui Osaka and Michio Iwaoka
Molecules 2017, 22(3), 354; https://doi.org/10.3390/molecules22030354 - 25 Feb 2017
Cited by 19 | Viewed by 6369
Abstract
We previously reported that water-soluble cyclic selenides can mimic the antioxidative function of glutathione peroxidase (GPx) in water through a simple catalytic cycle, in which the selenide (>Se) is oxidized by H2O2 to the selenoxide (>Se=O) and the selenoxide is [...] Read more.
We previously reported that water-soluble cyclic selenides can mimic the antioxidative function of glutathione peroxidase (GPx) in water through a simple catalytic cycle, in which the selenide (>Se) is oxidized by H2O2 to the selenoxide (>Se=O) and the selenoxide is reduced by a thiol back to the selenide. In methanol, however, the GPx-like activity could not be explained by this simple scenario. To look into the reasons for the unusual behaviors in methanol, monoamino-substituted cyclic selenides with a variable ring size were synthesized, and the intermediates of the catalytic cycle were characterized by means of 77Se-NMR and LC–MS spectroscopies. In water, it was confirmed that the selenide and the selenoxide mainly contribute to the antioxidative function, though a slight contribution from the dihydroxy selenane (>Se(OH)2) was also suggested. In methanol, on the other hand, other active species, such as hydroxyselenonium (>Se+–OH) and hydroxy perhydroxy selenane (>Se(OH)(OOH)), could be generated to build another catalytic cycle. This over-oxidation would be more feasible for amino-substituted cyclic selenides, probably because the ammonium (NH3+) group would transfer a proton to the selenoxide moiety to produce a hydroxyselenonium species in the absence of an additional proton source. Thus, a shift of the major catalytic cycle in methanol would make the GPx-like antioxidative function of selenides perplexing. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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823 KiB  
Article
Binding and Conversion of Selenium in Candida utilis ATCC 9950 Yeasts in Bioreactor Culture
by Marek Kieliszek, Stanisław Błażejak and Eliza Kurek
Molecules 2017, 22(3), 352; https://doi.org/10.3390/molecules22030352 - 25 Feb 2017
Cited by 37 | Viewed by 5537
Abstract
Selenium is considered an essential component of all living organisms. The use of yeasts as a selenium supplement in human nutrition has gained much interest over the last decade. The accumulation and biochemical transformation of selenium in yeast cells is particularly interesting to [...] Read more.
Selenium is considered an essential component of all living organisms. The use of yeasts as a selenium supplement in human nutrition has gained much interest over the last decade. The accumulation and biochemical transformation of selenium in yeast cells is particularly interesting to many researchers. In this article, we present the results of the determination of selenium and selenomethionine content in the biomass of feed yeast Candida utilis ATCC 9950 obtained from the culture grown in a bioreactor. The results indicated that C. utilis cells performed the biotransformation of inorganic selenium(IV) to organic derivatives (e.g., selenomethionine). Selenium introduced (20–30 mg Se4+∙L−1) to the experimental media in the form of sodium(IV) selenite (Na2SeO3) salt caused a significant increase in selenium content in the biomass of C. utilis,irrespective of the concentration. The highest amount of selenium (1841 μg∙gd.w.−1) was obtained after a 48-h culture in media containing 30 mg Se4+∙L−1. The highest content of selenomethionine (238.8 μg∙gd.w.−1) was found after 48-h culture from the experimental medium that was supplemented with selenium at a concentration of 20 mg Se4+∙L−1. Biomass cell in the cultures supplemented with selenium ranged from 1.5 to 14.1 g∙L−1. The results of this study indicate that yeast cell biomass of C. utilis enriched mainly with the organic forms of selenium can be a valuable source of protein. It creates the possibility of obtaining selenium biocomplexes that can be used in the production of protein-selenium dietary supplements for animals and humans Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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3849 KiB  
Article
Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol
by Gelson Perin, Angelita M. Barcellos, Eduardo Q. Luz, Elton L. Borges, Raquel G. Jacob, Eder J. Lenardão, Luca Sancineto and Claudio Santi
Molecules 2017, 22(2), 327; https://doi.org/10.3390/molecules22020327 - 20 Feb 2017
Cited by 20 | Viewed by 6496
Abstract
A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, [...] Read more.
A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60 °C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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1944 KiB  
Article
Synthesis and Single Crystal Structures of Substituted-1,3-Selenazol-2-amines
by Guoxiong Hua, Junyi Du, Alexandra M. Z. Slawin and J. Derek Woollins
Molecules 2017, 22(1), 46; https://doi.org/10.3390/molecules22010046 - 29 Dec 2016
Cited by 6 | Viewed by 5064
Abstract
The synthesis and X-ray single crystal structures of a series of new 4-substituted-1,3-selenazol-2-amines is reported. The efficient preparation of these compounds was carried out by two-component cyclization of the selenoureas with equimolar amounts of α-haloketones. The selenoureas were obtained from the reaction of [...] Read more.
The synthesis and X-ray single crystal structures of a series of new 4-substituted-1,3-selenazol-2-amines is reported. The efficient preparation of these compounds was carried out by two-component cyclization of the selenoureas with equimolar amounts of α-haloketones. The selenoureas were obtained from the reaction of Woollins’ reagent with cyanamides, followed by hydrolysis with water. All new compounds have been characterized by IR spectroscopy, multi-NMR (1H, 13C, 77Se) spectroscopy, accurate mass measurement and single crystal X-ray structure analysis. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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1452 KiB  
Article
Antimutagenic Effects of Selenium-Enriched Polysaccharides from Pyracantha fortuneana through Suppression of Cytochrome P450 1A Subfamily in the Mouse Liver
by Fan Peng, Xin Guo, Zhihong Li, Changzheng Li, Changdong Wang, Weiran Lv, Junjie Wang, Fangxiang Xiao, Mohammad Amjad Kamal and Chengfu Yuan
Molecules 2016, 21(12), 1731; https://doi.org/10.3390/molecules21121731 - 16 Dec 2016
Cited by 28 | Viewed by 5214
Abstract
Both selenium (Se) and polysaccharides from Pyracantha fortuneana (Maxim.) Li (PFPs) (P. fortuneana) have been reported to possess antioxidative and immuno-protective activities. Whether or not Se-containing polysaccharides (Se-PFPs) have synergistic effect of Se and polysaccharides on enhancing the antioxidant and immune [...] Read more.
Both selenium (Se) and polysaccharides from Pyracantha fortuneana (Maxim.) Li (PFPs) (P. fortuneana) have been reported to possess antioxidative and immuno-protective activities. Whether or not Se-containing polysaccharides (Se-PFPs) have synergistic effect of Se and polysaccharides on enhancing the antioxidant and immune activities remains to be determined. We previously reported that polysaccharides isolated from Se-enriched P. fortuneana (Se-PFPs) possessed hepatoprotective effects. However, it is not clear whether or not they have anti-mutagenic effects. In the present study, we compared and evaluated anti-mutagenic effects of Se-PFPs at three concentrations (1.35, 2.7 and 5.4 g/kg body weight) with those of PFPs, Se alone or Se + PFPs in mice using micronucleus assay in bone marrow and peripheral blood as well as mitomycin C-induced chromosomal aberrations in mouse testicular cells. We also elucidated the underlying mechanism. Our results demonstrated that Se-PFPs inhibited cyclophosphamide (CP)-induced micronucleus formation in both bone marrow and peripheral blood, enhanced the activities of superoxide dismutase (SOD) and glutathione peroxidase (GPx) in mouse liver, and reduced the activity and expression of cytochrome P450 1A (CYP4501A) in mouse liver in a dose-dependent manner. In addition, we found that the anti-mutagenic potential of Se-PFPs was higher than those of PFPs, Se alone or Se + PFPs at the same level. These results suggest that the anti-mutagenic potential of Se-PFPs may be mediated through the inhibition of the activity and expression of CYP4501A. This study indicates that application of Se-PFPs may provide an alternative strategy for cancer therapy by targeting CYP1A family. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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1755 KiB  
Article
The Protective Effect of Selenium on Chronic Zearalenone-Induced Reproductive System Damage in Male Mice
by Miao Long, Shuhua Yang, Yuan Wang, Peng Li, Yi Zhang, Shuang Dong, Xinliang Chen, Jiayi Guo, Jianbin He, Zenggui Gao and Jun Wang
Molecules 2016, 21(12), 1687; https://doi.org/10.3390/molecules21121687 - 07 Dec 2016
Cited by 36 | Viewed by 5879
Abstract
This study aims to explore the protective effect of selenium (Se) on chronic zearalenone (ZEN)-induced reproductive system damage in male mice and the possible protective molecular mechanism against this. The chronic ZEN-induced injury mouse model was established with the continuous intragastric administration of [...] Read more.
This study aims to explore the protective effect of selenium (Se) on chronic zearalenone (ZEN)-induced reproductive system damage in male mice and the possible protective molecular mechanism against this. The chronic ZEN-induced injury mouse model was established with the continuous intragastric administration of 40 mg/kg body mass (B.M.) ZEN for 28 days. Then, interventions with different doses (0.1, 0.2, and 0.4 mg/kg B.M.) of Se were conducted on mice to analyse the changes in organ indexes of epididymis and testis, antioxidant capability of testis, serum level of testosterone, sperm concentration and motility parameters, and the expression levels of apoptosis-associated genes and blood testis barrier- (BTB) related genes. Our results showed that Se could greatly improve the ZEN-induced decrease of epididymis indexes and testis indexes. Results also showed that the decrease in sperm concentration, sperm normality rate, and sperm motility parameters, including percentage of motile sperm (motile), tropism percentage (progressive) and sperm average path velocity (VAP), caused by ZEN were elevated upon administration of the higher dose (0.4 mg/kg) and intermediate dose (0.2 mg/kg) of Se. Selenium also significantly reduced the content of malondialdehyde (MDA) but enhanced the activities of antioxidant enzymes superoxide dismutase (SOD) and glutathione peroxidase (GPx) in the testis tissue. Further research demonstrated that ZEN increased the level of mRNA expression of BCL2-associated X protein (Bax) and caspase 3 (Casp3), decreased the level of mRNA expression of B cell leukemia/lymphoma 2 (Bcl2), vimentin (Vim) and cadherin 2 (Cdh2), whereas the co-administration of Se reversed these gene expression levels. Our results indicated that high levels of Se could protect against reproductive system damage in male mice caused by ZEN and the mechanism might such be that Se improved mice antioxidant ability, inhibited reproductive cell apoptosis, and increased the decrease of BTB integrity-related genes caused by ZEN. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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4602 KiB  
Article
Selenium Nanoparticles Attenuate Oxidative Stress and Testicular Damage in Streptozotocin-Induced Diabetic Rats
by Mohamed A. Dkhil, Rafat Zrieq, Saleh Al-Quraishy and Ahmed E. Abdel Moneim
Molecules 2016, 21(11), 1517; https://doi.org/10.3390/molecules21111517 - 19 Nov 2016
Cited by 86 | Viewed by 8654
Abstract
We investigated the protective and antioxidative effects of selenium nanoparticles (SeNPs) in streptozotocin STZ-induced diabetic rats. STZ-diabetic rats were exposed daily to treatments with SeNPs and/or insulin and then the effect of these treatments on the parameters correlated to oxidative damage of the [...] Read more.
We investigated the protective and antioxidative effects of selenium nanoparticles (SeNPs) in streptozotocin STZ-induced diabetic rats. STZ-diabetic rats were exposed daily to treatments with SeNPs and/or insulin and then the effect of these treatments on the parameters correlated to oxidative damage of the rat testes were assessed. Biochemical analysis revealed that SeNPs are able to ameliorate the reduction in the serum testosterone caused by STZ-induced diabetes. Furthermore, SeNPs could significantly decrease testicular tissue oxidative stress markers, namely lipid peroxidation and nitric oxide. In contrast, treatment of the STZ-diabetic rats with SeNPs increased the glutathione content and antioxidant enzyme activities in testicular tissues. Moreover, microscopic analysis proved that SeNPs are able to prevent histological damage in the testes of STZ-diabetic rats. Molecular analysis revealed that the mRNA level of Bcl-2 (B-cell lymphoma 2) is significantly upregulated. On the contrary, the mRNA level of Bax (Bcl-2 Associated X Protein) was significantly downregulated. Furthermore, treatment of STZ-diabetic rats with SeNPs led to an elevation in the expression of PCNA (Proliferating Cell Nuclear Antigen Gene). Interestingly, the insulin treatment also exhibited a significant improvement in the testicular function in STZ-diabetic rats. Collectively, our results demonstrated the possible effects of SeNPs in attenuating diabetes-induced oxidative damage, in particular in testicular tissue. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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Review

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256 KiB  
Review
Selenium Enrichment of Horticultural Crops
by Martina Puccinelli, Fernando Malorgio and Beatrice Pezzarossa
Molecules 2017, 22(6), 933; https://doi.org/10.3390/molecules22060933 - 04 Jun 2017
Cited by 107 | Viewed by 7897
Abstract
The ability of some crops to accumulate selenium (Se) is crucial for human nutrition and health. Selenium has been identified as a cofactor of the enzyme glutathione peroxidase, which is a catalyzer in the reduction of peroxides that can damage cells and tissues, [...] Read more.
The ability of some crops to accumulate selenium (Se) is crucial for human nutrition and health. Selenium has been identified as a cofactor of the enzyme glutathione peroxidase, which is a catalyzer in the reduction of peroxides that can damage cells and tissues, and can act as an antioxidant. Plants are the first link in the food chain, which ends with humans. Increasing the Se quantity in plant products, including leafy and fruity vegetables, and fruit crops, without exceeding the toxic threshold, is thus a good way to increase animal and human Se intake, with positive effects on long-term health. In many Se-enriched plants, most Se is in its major organic form. Given that this form is more available to humans and more efficient in increasing the selenium content than inorganic forms, the consumption of Se-enriched plants appears to be beneficial. An antioxidant effect of Se has been detected in Se-enriched vegetables and fruit crops due to an improved antioxidative status and to a reduced biosynthesis of ethylene, which is the hormone with a primary role in plant senescence and fruit ripening. This thus highlights the possible positive effect of Se in preserving a longer shelf-life and longer-lasting quality. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
2787 KiB  
Review
Electrophilic Selenium Catalysis with Electrophilic N-F Reagents as the Oxidants
by Ruizhi Guo, Lihao Liao and Xiaodan Zhao
Molecules 2017, 22(5), 835; https://doi.org/10.3390/molecules22050835 - 19 May 2017
Cited by 74 | Viewed by 8063
Abstract
A suitable oxidative system is crucial to electrophilic selenium catalysis (ESC). This short review offers the overview of recent development in ESC with electrophilic N-F reagents as the oxidants. Several highly selective transformations of alkenes such as allylic or vinylic imidation, pyridination, syn [...] Read more.
A suitable oxidative system is crucial to electrophilic selenium catalysis (ESC). This short review offers the overview of recent development in ESC with electrophilic N-F reagents as the oxidants. Several highly selective transformations of alkenes such as allylic or vinylic imidation, pyridination, syn-dichlorination, oxidative cyclization and asymmetric cyclization have been described. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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1551 KiB  
Review
Current Knowledge on the Importance of Selenium in Food for Living Organisms: A Review
by Marek Kieliszek and Stanisław Błażejak
Molecules 2016, 21(5), 609; https://doi.org/10.3390/molecules21050609 - 10 May 2016
Cited by 319 | Viewed by 17308
Abstract
Selenium is one of the elements classified within the group of micronutrients which are necessary in trace amounts for the proper functioning of organisms. Selenium participates in the protection of cells against excess H2O2, in heavy metal detoxification, and [...] Read more.
Selenium is one of the elements classified within the group of micronutrients which are necessary in trace amounts for the proper functioning of organisms. Selenium participates in the protection of cells against excess H2O2, in heavy metal detoxification, and regulation of the immune and reproductive systems as well. It also ensures the proper functioning of the thyroid gland. Selenium induces the occurrence of the selenoprotein synthesis process involved in the antioxidant defense mechanism of the organism. Recent years have brought much success in the studies on selenium. Anticarcinogenic properties of selenium against some cancers have been reported. Supplementation is increasingly becoming a solution to this problem. A large number of different supplementation methods are promoting studies in this area. Slight differences in the selenium content can result in excess or deficiency, therefore supplementation has to be done carefully and cautiously. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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