On-Demand Dissoluble Diselenide-Containing Hydrogel

Abstract

On-demand dissolution of hydrogels is being increasingly studied for their potential use in burn wound dressing applications. Herein, a dynamic diselenide-containing hydrogel is developed through a very simple one-pot and two-step process starting from the selenol functionalization of a partially hydrolyzed poly­(2-ethyl-2-oxazoline) with γ-butyroselenolactone. The hydrogel spontaneously cross-links via an in situ oxidation of the selenol functionalities in air. The gelation process and the final viscoelastic properties of the gel are characterized by rheological experiments. The mechanical properties of those new diselenide-containing hydrogels are easily tuned by varying the concentration of γ-butyroselenolactone. The materials also show good skin adhesion and UV light responsiveness. A unique feature of the hydrogel is its capability to be fully and rapidly dissolved on-demand, via oxidation or reduction of the diselenide cross-links, making them particularly attractive for burn wound dressing applications.

Kinetic Analysis of Degradation in Thioester Cross-linked Hydrogels as a Function of Thiol Concentration, pKa, and Presentation

“…Degradable hydrogels play key roles as a class of biomaterials and have applications in medical products such as controlled drug delivery systems, − carriers for cell delivery in vivo, and dissolvable wound dressings. , In addition, there are also recent examples of their utility in high technology applications, such as biofabrication and three-dimensional (3D) printing as applied to tissue engineering. , Many of these applications require cross-link chemistries that allow rapid and on-demand network degradation in the presence of cells and biologics . Enzymatic degradation, which proceeds quickly at low cross-link densities (<5 kPa), is considerably slower in more highly cross-linked systems.…”

Advances in the Stimuli‐Responsive Injectable Hydrogel for Controlled Release of Drugs

“…Better application in biological systems and material systems has been assumed for diselenide linkage-based hydrogels since diselenide bond energy is lower than disulfide bond and so its required dynamic chemistry condition seems to be milder than disulfide. A major obstacle to the development of diselenide-containing hydrogels is the poor solubility of Se-Se, [83] but Se-containing polymers are currently leaving their infancy and gaining good application in the fabrication of hydrogels [84,85] and micelles. [86,87] Nowadays, there have been several reported hydrogels with Se-Se-linkage that exhibit prominent ROS-and GSH responsiveness.…”

Diselenide–yne chemistry for selenium-containing linear polymer modification

“…1 Thus, small molecule selenides have been widely used in organic synthesis. 2,3 In addition, due to the inherent characteristics of selenium atoms, selenium-containing polymers have unique properties, such as redox, 4,5 light, 6,7 radiation 8,9 and coordination 10,11 responsiveness, and have been widely used in different fields, including smart nanocarriers, 12,13 enzyme mimics, 14,15 shape memory materials, 7,16 and self-healing materials. 17–19 Due to the unique photo-reactivity and dynamic nature of the Se–Se bond, diselenide-containing polymers are being more extensively studied.…”