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

Abstract

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 1 H-NMR, 13 C-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 OPEN ACCESSMolecules 2015, 20 10096 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.

Engineering folate-targeting diselenide-containing triblock copolymer as a redox-responsive shell-sheddable micelle for antitumor therapy in vivo

“…Diselenide was prepared as previously described ( Fig. 1A) [34]. Briefly, elemental Se (0.157 g, 1.99 mmol) and NaBH 4 (0.152 g, 3.98 mmol) were placed in a two-neck round-bottom flask and mixed under nitrogen gas flow.…”

“…In vitro release profiles of PTX from micelles were investigated in three different buffers (all containing 1 M sodium salicylate) of PBS (0.01 mol/L, 1 M sodium salicylate, pH 7.4), 2 mM GSH, and 0.1 wt. % H 2 O 2 by the diffusion technique using a dialysis bag [34]. Drug-loaded micelles (1.5 mL) were introduced into a dialysis membrane tubing (Spectra, MWCO=3.5 kDa) and incubated in 25 mL of buffer at 37°C.…”

Reaction of bis[(2-chlorocarbonyl)phenyl] Diselenide with Phenols, Aminophenols, and Other Amines towards Diphenyl Diselenides with Antimicrobial and Antiviral Properties

“…However, in the absence of the soft electrophilic center, no side reactions should occur. Thus, we expected that the reaction of bis[(2-chlorocarbonyl)phenyl] diselenide 3 with aminophenols could be considered as a convenient alternative for low-efficient reductive ring opening of ebselenols [ 53 ] and the preparation from 2,2’-dicarboxydiphenyl diselenide using active ester coupling agents [ 23 , 61 ], where the protection of the hydroxyl group would be recommended.…”

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

“…A similar synthetic strategy was adopted by Rafique et al to prepare a small set of aliphatic and aromatic diselenide derivatives of 2-picolylamide with spacers of different length between the Se atoms and the heteroatoms of the amides [171]. The aim of the authors was to optimize the spacer for an optimal reproduction of the distances measured in the catalytic site of GPx.…”