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

Molecules

Jamal Rafique³  Sumbal Saba³  Rômulo Faria Santos Canto³  Tiago Elias Allievi Frizon³  Waseem Hassan²  Emily Pansera Waczuk²  Maryam Jan¹  Davi Fernando Back⁴  João Batista Teixeira Da Rocha²  Antonio Luiz Braga³ 

[1] Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, KPK, Pakistan; E-Mail:;Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, Brazil; E-Mails:;Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil; E-Mails:;Departamento de Química, Laboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, UFSM, Santa Maria 97115-900, RS, Brazil; E-Mail:

关键词: diselenides;    2-picolylamide;    TPx;    TBARS;   

DOI  :  10.3390/molecules200610095

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.