Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions
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...
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MDPI AG
2015-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/6/10095 |
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| author | Jamal Rafique Sumbal Saba Rômulo Faria Santos Canto Tiago Elias Allievi Frizon Waseem Hassan Emily Pansera Waczuk Maryam Jan Davi Fernando Back João Batista Teixeira Da Rocha Antonio Luiz Braga |
| author_facet | Jamal Rafique Sumbal Saba Rômulo Faria Santos Canto Tiago Elias Allievi Frizon Waseem Hassan Emily Pansera Waczuk Maryam Jan Davi Fernando Back João Batista Teixeira Da Rocha Antonio Luiz Braga |
| author_sort | Jamal Rafique |
| collection | DOAJ |
| description | 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 1H-NMR, 13C-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 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. |
| first_indexed | 2024-12-21T23:34:23Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T23:34:23Z |
| publishDate | 2015-06-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-b287bf98e7a14ce3a2f70df2aad5aa332022-12-21T18:46:25ZengMDPI AGMolecules1420-30492015-06-01206100951010910.3390/molecules200610095molecules200610095Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded InteractionsJamal Rafique0Sumbal Saba1Rômulo Faria Santos Canto2Tiago Elias Allievi Frizon3Waseem Hassan4Emily Pansera Waczuk5Maryam Jan6Davi Fernando Back7João Batista Teixeira Da Rocha8Antonio Luiz Braga9Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, BrazilDepartamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, BrazilDepartamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, BrazilDepartamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, BrazilDepartamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, BrazilDepartamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, BrazilInstitute of Chemical Sciences, University of Peshawar, Peshawar 25120, KPK, PakistanDepartamento de Química, Laboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, UFSM, Santa Maria 97115-900, RS, BrazilDepartamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, BrazilDepartamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, BrazilIn 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 1H-NMR, 13C-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 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.http://www.mdpi.com/1420-3049/20/6/10095diselenides2-picolylamideTPxTBARS |
| spellingShingle | Jamal Rafique Sumbal Saba Rômulo Faria Santos Canto Tiago Elias Allievi Frizon Waseem Hassan Emily Pansera Waczuk Maryam Jan Davi Fernando Back João Batista Teixeira Da Rocha Antonio Luiz Braga Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions Molecules diselenides 2-picolylamide TPx TBARS |
| title | Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions |
| title_full | Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions |
| title_fullStr | Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions |
| title_full_unstemmed | Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions |
| title_short | Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions |
| title_sort | synthesis and biological evaluation of 2 picolylamide based diselenides with non bonded interactions |
| topic | diselenides 2-picolylamide TPx TBARS |
| url | http://www.mdpi.com/1420-3049/20/6/10095 |
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