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Molecules 2015, 20(6), 10095-10109;

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

Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil
Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, Brazil
Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, KPK, Pakistan
Departamento de Química, Laboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, UFSM, Santa Maria 97115-900, RS, Brazil
These authors contributed equally to this work.
Author to whom correspondence should be addressed.
Academic Editor: Thomas G. Back
Received: 30 April 2015 / Revised: 23 May 2015 / Accepted: 27 May 2015 / Published: 1 June 2015
(This article belongs to the Special Issue Selenium Catalysts and Antioxidants)
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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. View Full-Text
Keywords: diselenides; 2-picolylamide; TPx; TBARS diselenides; 2-picolylamide; TPx; TBARS

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Rafique, J.; Saba, S.; Canto, R.F.S.; Frizon, T.E.A.; Hassan, W.; Waczuk, E.P.; Jan, M.; Back, D.F.; Da Rocha, J.B.T.; Braga, A.L. Synthesis and Biological Evaluation of 2-Picolylamide-Based Diselenides with Non-Bonded Interactions. Molecules 2015, 20, 10095-10109.

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