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Advances in Selenium Catalysts and Antioxidants
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Special Issue "Advances in Selenium Catalysts and Antioxidants"

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

Deadline for manuscript submissions: 30 September 2023 | Viewed by 1890

Special Issue Editors

Prof. Dr. Michio Iwaoka

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Guest Editor
Department of Chemistry, School of Science, Tokai University, Kanagawa, Japan
Interests: selenium chemistry; protein chemistry
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Claudio Santi

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Guest Editor
Department of Pharmaceutical Sciences, Group of Catalysis and Organic Green Chemistry, University of Perugia, 06123 Perugia, PG, Italy
Interests: selenium and sulfur chemistry; redox catalysis; bioorganic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Selenium (Se) has recently become an important element in a diverse range of research fields, such as biology, biomimetic chemistry, medicinal chemistry, organic synthesis, material science, etc., owing to its characteristic redox behaviors, which are similar but discretely different from those of sister chalcogen elements such as sulfur (S) and tellurium (Te). In this special issue of Molecules, we invite original research articles and reviews on related topics, focusing on the latest advances in selenium catalysts and antioxidants.

Prof. Dr. Michio Iwaoka
Prof. Dr. Claudio Santi
Guest Editors

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 2300 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

  • selenoenzyme models
  • selenosugars
  • biomimetics
  • reactive oxygen species
  • nanoparticles
  • chalcogen bond
  • catalytic reactions
  • organoselenium compounds

Published Papers (3 papers)

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Article
Chemistry Related to the Catalytic Cycle of the Antioxidant Ebselen
by
Kai N. Sands
,
Austin L. Burman
,
Esther Ansah-Asamoah
and
Thomas G. Back
Molecules 2023, 28(9), 3732; https://doi.org/10.3390/molecules28093732 - 26 Apr 2023
Viewed by 490
Abstract
The antioxidant drug ebselen has been widely studied in both laboratories and in clinical trials. The catalytic mechanism by which it destroys hydrogen peroxide via reduction with glutathione or other thiols is complex and has been the subject of considerable debate. During reinvestigations [...] Read more.
The antioxidant drug ebselen has been widely studied in both laboratories and in clinical trials. The catalytic mechanism by which it destroys hydrogen peroxide via reduction with glutathione or other thiols is complex and has been the subject of considerable debate. During reinvestigations of several key steps, we found that the seleninamide that comprises the first oxidation product of ebselen underwent facile reversible methanolysis to an unstable seleninate ester and two dimeric products. In its reaction with benzyl alcohol, the seleninamide produced a benzyl ester that reacted readily by selenoxide elimination, with formation of benzaldehyde. Oxidation of ebselen seleninic acid did not afford a selenonium seleninate salt as previously observed with benzene seleninic acid, but instead generated a mixture of the seleninic and selenonic acids. Thiolysis of ebselen with benzyl thiol was faster than oxidation by ca. an order of magnitude and produced a stable selenenyl sulfide. When glutathione was employed, the product rapidly disproportionated to glutathione disulfide and ebselen diselenide. Oxidation of the S-benzyl selenenyl sulfide, or thiolysis of the seleninamide with benzyl thiol, afforded a transient thiolseleninate that also readily underwent selenoxide elimination. The S-benzyl derivative disproportionated readily when catalyzed by the simultaneous presence of both the thiol and triethylamine. The phenylthio analogue disproportionated when exposed to ambient or UV (360 nm) light by a proposed radical mechanism. These observations provide additional insight into several reactions and intermediates related to ebselen. Full article
(This article belongs to the Special Issue Advances in Selenium Catalysts and Antioxidants)
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Article
Controlling the Redox Catalytic Activity of a Cyclic Selenide Fused to 18-Crown-6 by the Conformational Transition Induced by Coordination to an Alkali Metal Ion
by
Michio Iwaoka
,
Hajime Oba
and
Takeru Ito
Molecules 2023, 28(8), 3607; https://doi.org/10.3390/molecules28083607 - 20 Apr 2023
Viewed by 422
Abstract
trans-3,4-Dihydroxyselenolane (DHS), a water-soluble cyclic selenide, exhibits selenoenzyme-like unique redox activities through reversible oxidation to the corresponding selenoxide. Previously, we demonstrated that DHS can be applied as an antioxidant against lipid peroxidation and a radioprotector by means of adequate modifications of the [...] Read more.
trans-3,4-Dihydroxyselenolane (DHS), a water-soluble cyclic selenide, exhibits selenoenzyme-like unique redox activities through reversible oxidation to the corresponding selenoxide. Previously, we demonstrated that DHS can be applied as an antioxidant against lipid peroxidation and a radioprotector by means of adequate modifications of the two hydroxy (OH) groups. Herein, we synthesized new DHS derivatives with a crown-ether ring fused to the OH groups (DHS-crown-n (n = 4 to 7), 1–4) and investigated their behaviors of complex formation with various alkali metal salts. According to the X-ray structure analysis, it was found that the two oxygen atoms of DHS change the directions from diaxial to diequatorial by complexation. The similar conformational transition was also observed in solution NMR experiments. The 1H NMR titration in CD3OD further confirmed that DHS-crown-6 (3) forms stable 1:1 complexes with KI, RbCl and CsCl, while it forms a 2:1 complex with KBPh4. The results suggested that the 1:1 complex (3·MX) exchanges the metal ion with metal-free 3 through the formation of the 2:1 complex. The redox catalytic activity of 3 was evaluated using a selenoenzyme model reaction between H2O2 and dithiothreitol. The activity was significantly reduced in the presence of KCl due to the complex formation. Thus, the redox catalytic activity of DHS could be controlled by the conformational transition induced by coordination to an alkali metal ion. Full article
(This article belongs to the Special Issue Advances in Selenium Catalysts and Antioxidants)
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Article
Selenonium Salt as a Catalyst for Nucleophilic Substitution Reactions in Water: Synthesis of Thiocyanites and Selenocyanates
by
Alix Y. Bastidas Ángel
,
Philipe Raphael O. Campos
and
Eduardo E. Alberto
Molecules 2023, 28(7), 3056; https://doi.org/10.3390/molecules28073056 - 29 Mar 2023
Viewed by 687
Abstract
Organothiocyanates and selenocyanates are valuable compounds, both in terms of functional group interconversion and due to their biological activities. In this contribution, we report the synthesis of a series of these important substances in a mixture of water and dimethyl carbonate (20/1 proportion) [...] Read more.
Organothiocyanates and selenocyanates are valuable compounds, both in terms of functional group interconversion and due to their biological activities. In this contribution, we report the synthesis of a series of these important substances in a mixture of water and dimethyl carbonate (20/1 proportion) using potassium thio- or selenocyanates salts and organic bromides. The key to the effectiveness of the reaction is a chalcogen bond interaction between a selenonium salt catalyst and the organic substrate. Full article
(This article belongs to the Special Issue Advances in Selenium Catalysts and Antioxidants)
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