Next Article in Journal
Application of the Cre/loxP Site-Specific Recombination System for Gene Transformation in Aurantiochytrium limacinum
Next Article in Special Issue
Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents
Previous Article in Journal
PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp.
Previous Article in Special Issue
Xerogel-Sequestered Silanated Organochalcogenide Catalysts for Bromination with Hydrogen Peroxide and Sodium Bromide
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(6), 10095-10109; doi:10.3390/molecules200610095

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

1
Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil
2
Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, Brazil
3
Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, KPK, Pakistan
4
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)
View Full-Text   |   Download PDF [999 KB, uploaded 1 June 2015]   |  

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 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
Figures

Figure 1

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).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top