Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics
Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/15/4446 |
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| author | Giancarlo V. Botteselle Welman C. Elias Luana Bettanin Rômulo F. S. Canto Drielly N. O. Salin Flavio A. R. Barbosa Sumbal Saba Hugo Gallardo Gianluca Ciancaleoni Josiel B. Domingos Jamal Rafique Antonio L. Braga |
| author_facet | Giancarlo V. Botteselle Welman C. Elias Luana Bettanin Rômulo F. S. Canto Drielly N. O. Salin Flavio A. R. Barbosa Sumbal Saba Hugo Gallardo Gianluca Ciancaleoni Josiel B. Domingos Jamal Rafique Antonio L. Braga |
| author_sort | Giancarlo V. Botteselle |
| collection | DOAJ |
| description | Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium. |
| first_indexed | 2024-03-10T09:11:05Z |
| format | Article |
| id | doaj.art-5ed3b569fb7744dbb50e46937ac87b9c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T09:11:05Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5ed3b569fb7744dbb50e46937ac87b9c2023-11-22T05:58:12ZengMDPI AGMolecules1420-30492021-07-012615444610.3390/molecules26154446Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx MimicsGiancarlo V. Botteselle0Welman C. Elias1Luana Bettanin2Rômulo F. S. Canto3Drielly N. O. Salin4Flavio A. R. Barbosa5Sumbal Saba6Hugo Gallardo7Gianluca Ciancaleoni8Josiel B. Domingos9Jamal Rafique10Antonio L. Braga11Departamento de Química, Universidade Estadual do Centro-Oeste (UNICENTRO), Guarapuava 85040-167, PR, BrazilDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilPrograma de Pós-Graduação em Ciências da Saúde, Universidade Federal de Ciências da Saúde de Porto Alegre (UFCSPA), Porto Alegre 90050-170, RS, BrazilDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilInstituto de Química—IQ, Universidade Federal de Goiás—(UFG), Goiânia 74690-900, GO, BrazilDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilDepartment of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, I-56124 Pisa, ItalyDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilInstituto de Química—INQUI, Universidade Federal do Mato Grosso do Sul (UFMS), Campo Grande 79074-460, MS, BrazilDepartamento de Química, Universidade Federal de Santa Catarina (UFSC), Florianópolis 88040-970, SC, BrazilHerein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.https://www.mdpi.com/1420-3049/26/15/4446organoselenidesGPxDFTnon-bonding interactiondiselenidesanilines |
| spellingShingle | Giancarlo V. Botteselle Welman C. Elias Luana Bettanin Rômulo F. S. Canto Drielly N. O. Salin Flavio A. R. Barbosa Sumbal Saba Hugo Gallardo Gianluca Ciancaleoni Josiel B. Domingos Jamal Rafique Antonio L. Braga Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics Molecules organoselenides GPx DFT non-bonding interaction diselenides anilines |
| title | Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics |
| title_full | Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics |
| title_fullStr | Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics |
| title_full_unstemmed | Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics |
| title_short | Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics |
| title_sort | catalytic antioxidant activity of bis aniline derived diselenides as gpx mimics |
| topic | organoselenides GPx DFT non-bonding interaction diselenides anilines |
| url | https://www.mdpi.com/1420-3049/26/15/4446 |
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