Novel sulfur and selenium-containing antioxidants: Synthesis and evaluation of their GPx-like activity

Tanini, Damiano; D'Esopo, Veronica; Chen, Dan; Barchielli, Giulia; Capperucci, Antonella

doi:10.1080/10426507.2016.1252365

Cited by 27 publications

(8 citation statements)

References 12 publications

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“…Thus, having developed a novel procedure for the synthesis of small molecules containing the S-Se moiety, we sought to preliminary test their GPx-like activity. The thiol peroxidase-like activity of compounds 3h and 3l was studied according to the DTT oxidation test (Figure 1) [33][34][35]. Indeed, selenenylsulfides 3h,l behaved as medium effective catalysts with T 50 around 70 min [36] Furthermore, in line with previous findings on the antioxidant properties of different organoselenium compounds [37,38], the presence of a methoxy group onto the arylseleno moiety renders selenenylsulfide 3l more efficient than 3h (Figure 1).…”

Section: Resultssupporting

confidence: 71%

Section: Resultsmentioning

confidence: 99%

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Towards New Catalytic Antioxidants: A Simple and Mild Synthesis of Selenenylsulfides

Tanini¹,

Bonardi²,

Viglianisi³

et al. 2019

Catalysts

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A new methodology for the synthesis of small molecules containing the S-Se bond is reported. Aryl-and alkyl-selenols react smoothly with N-thiophthalimides to afford the corresponding selenenylsulfides through a clean S N 2 path occurring at the sulfur atom. The reaction proceeds under very mild conditions in DMF in absence of catalysts for most of the substrates. The scope of the reaction was found to be broad, allowing a wide series of selenols and N-thiophtalimides to be efficiently employed in this procedure. Owing to the instability of the S-Se bond, selenenylsulfides exhibited a remarkable tendency to disproportionate to the corresponding symmetric diselenides and disulfides. Preliminary evaluation of the catalytic antioxidant properties of novel selenenylsulfides showed their behaviour as GPx mimics.Catalysts 2019, 9, 333 2 of 11 a second equivalent of GSH, to reform the selenol, together with oxidized glutathione GSSG. The selenenylsulfide, containing the Se-S bridge, represents the key intermediate for the activity of the enzyme [7,[16][17][18][19]. Taking into account the importance of this process, several synthetic approaches to obtain selenated small molecules as enzyme mimics have been developed. However, to the best of our knowledge, a limited number of methods are reported for the preparation of selenenylsulfides. These methods typically exploited the reactivity of diselenides in thiol-diselenide exchange or foresee the reaction of sulfenyl derivatives with thiols [16,17,[20][21][22].It is well established that the Se-S bridge is unstable and undergoes disproportionation reaction to afford diselenides and disulfides. Some examples are reported on selenenylsulfides stabilized by sterically bulky groups or by intramolecular Se . . . Het (N, O) interactions [23].Owing to the interest in these selenium containing compounds, the search for novel procedures to prepare small molecules containing the Se-S unit is of great interest.Our long-dated interest in the chemistry of silyl chalcogenides allowed to disclose novel procedures to access a plethora of sulfur and selenium containing molecules exploiting the nucleophilic behaviour of the chalcogen atom towards various electrophiles [24][25][26][27][28][29]. Recently we reported the reaction of bis(trimethylsilyl)selenide (HMDSS) with N-thiophtalimides as a mild, general metal free procedure for the synthesis of variously substituted disulfides [30].Indeed, despite the interest in the reactivity of selenols as nucleophilic selenium transfer reagents, their use has been critically limited by their instability. However, HMDSS was efficient in the opening of ring strained heterocycles, namely epoxides, episulfides and aziridines, leading to a wide range of β-functionalized selenols, which were stable enough to react with electrophiles under controlled catalytic conditions [31]. Differently substituted stable aryl selenols were also prepared by reduction of the parent diselenides to explore their activity as enzyme inhibitors [32].On the basis of our findings ...

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Section: Resultssupporting

confidence: 71%

Section: Resultsmentioning

confidence: 99%

Towards New Catalytic Antioxidants: A Simple and Mild Synthesis of Selenenylsulfides

Tanini¹,

Bonardi²,

Viglianisi³

et al. 2019

Catalysts

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“…Having disclosed novel procedures for the synthesis of unreported functionalized cyclic and open‐chain selenides, we next preliminary evaluated their catalytic antioxidant activity as GPx mimics. Therefore, the thiol peroxidase‐like properties of selected compounds were determined by using both the DTT oxidation text,,, and the GSH/GR coupled assay ,,. Results of this investigation are reported in Figures and .…”

Section: Resultsmentioning

confidence: 99%

“…GPx‐like activity measurments . Glutathione peroxidase‐like activity was evaluated following reported procedures ,,,…”

Section: Methodsmentioning

confidence: 99%

Seleno‐Michael Reaction of Stable Functionalised Alkyl Selenols: A Versatile Tool for the Synthesis of Acyclic and Cyclic Unsymmetrical Alkyl and Vinyl Selenides

et al. 2019

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Seleno-Michael additions of stable functionalised primary alkyl selenols to activated alkenes and alkynes are described. In the presence of Al 2 O 3 , β-hydroxy-, β-amino-, and β-mercapto selenols react smoothly with electron-poor alkenes and alkynes to afford the corresponding unsymmetrical functionalised dialkyl-and alkylÀ vinyl-selenides in good yield. The very mild conditions allow a broad range of selenols and Michael acceptors to be converted into the corresponding synthetically valuable seleno-Michael adducts, demonstrating high selectivity and excellent functional group tolerance. Hydroxy-and mercapto-substituted vinyl selenides were efficiently employed for the synthesis of functionalised 1,3-oxaselenolanes, 1,3-thiaselenolanes, and 1,4thiaselenanes through intramolecular oxa-and thia-Michael additions. Furthermore, a NaH-promoted lactonization enables the synthesis of variously substituted 2-oxo-1,4-oxaselenanes from hydroxyÀ vinylselenides. Evaluation of thiol peroxidase-like properties of novel functionalised organoselenides demonstrated that they possess a remarkable catalytic antioxidant activity.

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“…In order to develop novel hCA activators with antioxidant properties, we also evaluated the thiol peroxidase-like properties of selected β-arylchalcogeno amines. Therefore, the activity of sulfides 3a,c, selenides 5a,e,l and tellurides 7a-c,f as mimics of glutathione peroxidase (GPx) was assessed by using the dithiothreitol (DTT) oxidation test [36][37][38][39] and the GSH/GR coupled assay. [39][40] Results of this investigation are reported in Table 2.…”

Section: Antioxidant Assaysmentioning

confidence: 99%

Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators

Tanini

Capperucci

Supuran

2019

Bioorganic Chemistry

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A new series of β-aminochalcogenides were designed and synthesized to identify new carbonic anhydrase activator (CAA) agents as novel tools for the management of several neurodegenerative and metabolic disorders which represent a clinical challenge without effective therapies available. Some β-aminoselenides and β-aminotellurides showed effective CA activating effects and a potent antioxidant activity. CAAs may have applications for memory therapy and CA deficiency syndromes.

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Novel sulfur and selenium-containing antioxidants: Synthesis and evaluation of their GPx-like activity

Cited by 27 publications

References 12 publications

Towards New Catalytic Antioxidants: A Simple and Mild Synthesis of Selenenylsulfides

Towards New Catalytic Antioxidants: A Simple and Mild Synthesis of Selenenylsulfides

Seleno‐Michael Reaction of Stable Functionalised Alkyl Selenols: A Versatile Tool for the Synthesis of Acyclic and Cyclic Unsymmetrical Alkyl and Vinyl Selenides

Sulfur, selenium and tellurium containing amines act as effective carbonic anhydrase activators

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