Addition of butoxycarbonyl group to phenylalanine derived chalcogenide increases the toxic potential: Importance of non-bonding nitrogen interaction

Hassan, Waseem; Schiar, Viviane Patrícia Pires; Santos, Danúbia Bonfanti; Duarte, Marta M. M. F.; Vargas, Fabrı́cio; Nogueira, Cristina W.; Zeni, Gilson; Braga, Antônio L.; Rocha, João Batista Teixeira da

doi:10.1016/j.cbi.2013.10.017

Cited by 2 publications

(5 citation statements)

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“…[7] Glutathione peroxidases (Gpx) are selenoenzymes responsible for scavenging peroxides and hydrogen peroxide at the expense of glutathione (GSH), preventing oxidative damage. [8] Additionally, organoselenium compounds are widely related to biological and medicinal properties, [9,10,11] as well as might provide SARS-CoV-2 infection control. [12] The selenium moiety can be introduced in an organic substrate through electrophilic, nucleophilic and radical pathways.…”

Section: Introductionmentioning

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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Section: Introductionmentioning

confidence: 99%

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

et al. 2020

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“…However, it is interesting to note that employing butoxycarbonyl (BOC group), which usually blocks the interactions in synthetic routes, significantly reduced the TPx-like potential of chalcogenides [32]. In fact, the addition of BOC to amino-acid derived diselenides increased the toxic potential apparent from considerably increased ALT activity, serum creatinine and triglyceride levels after in vivo treatment in mice [34]. Although not very relevant to selenium molecules, but only to depict the diverse scenarios, we have obtained persuasive evidence that nonbonding interactions can also significantly interact with sulfur (disulfides) [32].…”

Section: Resultsmentioning

confidence: 99%

“…Aromatization of this side chain restricts the possible conformations and thus favors the interaction. Based on experimental TPx activity, XRD analysis and relevant literature [32,34,50,51] we can assume the important catalytic influence of nonbonding interactions.…”

Section: Resultsmentioning

confidence: 99%

“…In this context, our group has recently synthesized diselenides with heteroatoms in close proximity to the selenium atom with interesting GPx-like activity [30,31]. In fact, we have provided conclusive and baseline data that the presence of proximal heteroatom drastically affect GPx-like activity which furthermore enhances both in vitro and in vivo antioxidant activity with negligible toxicity [32,33,34].…”

Section: Introductionmentioning

confidence: 99%

“…As part of our wider research program aimed at designing and developing biologically active new organoselenium compounds [15,32,33,34], herein we report a series of 2-picolylamide-based diselenides with proximal non-bonded interactions. The focus of the present paper is to address and explore the synthetic avenues and biosignificance of diselenides with amide groups in close proximity i.e.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions

et al. 2015

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Abstract:In this paper, we report the synthesis and biological evaluation of picolylamide-based diselenides with the aim of developing a new series of diselenides with O···Se non-bonded interactions. The synthesis of diselenides was performed by a simple and efficient synthetic route. All the products were obtained in good yields and their structures were determined by 1 H-NMR, 13 C-NMR and HRMS. All these new compounds showed promising activities when tested in different antioxidant assays. These amides exhibited strong thiol peroxidase-like (TPx) activity. In fact one of the compounds showed 4.66 times higher potential than the classical standard i.e., diphenyl diselenide. The same compound significantly inhibited iron (Fe)-induced thiobarbituric acid reactive species (TBARS) production in rat's brain homogenate. In addition, the X-ray structure of the most active OPEN ACCESSMolecules 2015, 20 10096 compound showed non-bonded interaction between the selenium and the oxygen atom that are in close proximity and may be responsible for the increased antioxidant activity. The present study provides evidence about the possible biochemical influence of nonbonding interactions on organochalcogens potency.

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Addition of butoxycarbonyl group to phenylalanine derived chalcogenide increases the toxic potential: Importance of non-bonding nitrogen interaction

Cited by 2 publications

References 17 publications

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

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

Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions

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