Organic selenocompounds: are they the panacea for human illnesses?

Rocha, João Batista Teixeira da; Nogara, Pablo Andrei; Pereira, Meire Ellen; Oliveira, Cláudia S.; Orian, Laura

doi:10.1039/d2nj05694a

Cited by 7 publications

(3 citation statements)

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“…Such a highly electrophilic character of a cyclic selenenyl amide is consistent with the nonbonding interactions between the oxygen atom of the solvent Et 2 O molecule and the selenium atom of the cyclic selenenyl amide moiety in the crystal structures of 2 a and 2 b (Figure 5). Although Sec‐derived cyclic selenenyl amides have been proposed as protective forms for suppressing the degradation of Sec–SeOHs in GPx, [22] these results suggest that they could play potential roles as highly electrophilic intermediates [9] in various selenoproteins.…”

Section: Resultsmentioning

confidence: 96%

“…Selenocysteines (Sec) are involved in several enzymes, [1] such as glutathione peroxidase (GPx) [2][3][4] (one of the most important antioxidant enzymes for mammalians [5,6] ) and thioredoxin reductase (a central component in the thioredoxin system). [7,8] In the catalytic cycle of these selenoenzymes, the generation of Sec-derived electrophilic reactive species [9,10] as key intermediates has been widely accepted. This is exemplified by the formation of Sec selenenic acids (Sec-SeOHs) [11] through the H 2 O 2 oxidation of Sec selenols (Sec-SeHs) in the catalytic site of GPx (Figure 1a, step A).…”

Section: Introductionmentioning

confidence: 99%

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Highly Electrophilic Intermediates in the Bypass Mechanism of Glutathione Peroxidase: Synthesis, Reactivity, and Structures of Selenocysteine‐Derived Cyclic Selenenyl Amides

Masuda,

Karasaki,

Sase

et al. 2023

Chemistry A European J

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Selenocysteine (Sec)‐derived cyclic selenenyl amides, formed by the intramolecular cyclization of Sec selenenic acids (Sec–SeOHs), have been postulated to function as protective forms in the bypass mechanism of glutathione peroxidase (GPx). However, their chemical properties have not been experimentally elucidated in proteins or small‐molecule systems. Recently, we reported the first nuclear magnetic resonance observation of Sec–SeOHs and their cyclization to the corresponding cyclic selenenyl amides using selenopeptide model systems incorporated in a molecular cradle. Herein, we elucidate the structures and reactivities of Sec‐derived cyclic selenenyl amides. The crystal structures and reactions toward a cysteine thiol or a 1,3‐diketone‐type chemical probe indicated the highly electrophilic character of cyclic selenenyl amides. This suggests that they can serve not only as protective forms to suppress the inactivation of Sec–SeOHs in GPx but also as highly electrophilic intermediates in the reactions of selenoproteins.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Highly Electrophilic Intermediates in the Bypass Mechanism of Glutathione Peroxidase: Synthesis, Reactivity, and Structures of Selenocysteine‐Derived Cyclic Selenenyl Amides

Masuda,

Karasaki,

Sase

et al. 2023

Chemistry A European J

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“…4 It is not a coincidence that nature has chosen selenium due to its unique ability to react with oxygen and related ROS in a readily reversible manner, being able to both rapidly become oxidized and then be rapidly reduced (referred to as the “selenium paradox”). 5 To mimic the intracellular GPx antioxidant activity, some organoselenium compounds 6 and selenium (Se)-containing nanomaterials 7 have been investigated with pharmacological purposes.…”

Section: Introductionmentioning

confidence: 99%

A selenoureido-iminoglycolipid transported by zeolitic-imidazolate framework nanoparticles: a novel antioxidant therapeutic approach

Guerrero,

Carmona,

Vidal

et al. 2023

Nanoscale Horiz.

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Organoselenium Compounds in Medicinal Chemistry

Gallo‐Rodriguez,

Rodriguez

2024

ChemMedChem

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The chemical and biological interest in this element and the molecules bearing selenium has been exponentially growing over the years. Selenium, formerly designated as a toxin, becomes a vital trace element for life that appears as selenocysteine and its dimeric form, selenocystine, in the active sites of selenoproteins, which catalyze a wide variety of reactions, including the detoxification of reactive oxygen species and modulation of redox activities. From the point of view of drug developments, organoselenium drugs are isosteres of sulfur‐containing and oxygen—containing drugs with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. This statement is the paramount relevance considering the big number of clinically employed compounds bearing sulfur or oxygen atoms if their structures including nucleosides and carbohydrates. Thus, in this article we have focused on the relevant features of the application of selenium in medicinal chemistry. With the increasing interest in selenium chemistry, we have attempted to highlight the most significant published data on this subject, mainly concentrating the analysis on the last years. In consequence, the recent advances of relevant pharmacological organoselenium compounds are discussed.

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Organic selenocompounds: are they the panacea for human illnesses?

Abstract: The selenium element is essential of some life forms and its biological-chemistry function is mainly performed by the selenol/selenolate moiety (-SeH/-Se-) in a few selenoproteins. Many synthetic organoselenium compounds (OSeCs)...

Cited by 7 publications

References 358 publications

Highly Electrophilic Intermediates in the Bypass Mechanism of Glutathione Peroxidase: Synthesis, Reactivity, and Structures of Selenocysteine‐Derived Cyclic Selenenyl Amides

Highly Electrophilic Intermediates in the Bypass Mechanism of Glutathione Peroxidase: Synthesis, Reactivity, and Structures of Selenocysteine‐Derived Cyclic Selenenyl Amides

A selenoureido-iminoglycolipid transported by zeolitic-imidazolate framework nanoparticles: a novel antioxidant therapeutic approach

Organoselenium Compounds in Medicinal Chemistry

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