Poly(vinyl alcohol) Modified via the Hantzsch Reaction for Biosafe Antioxidant Self-Healing Hydrogel

Abstract

Efficient routes for the preparation of functional self-healing hydrogels from functional polymers are needed. In this study, we developed a strategy to effectively produce a vanillinmodified poly(vinyl alcohol) (PVA-vanillin) through the Hantzsch reaction. This polymer was cross-linked with a phenylboronic acidcontaining polymer (PB) that was also prepared using the Hantzsch reaction to fabricate a hydrogel through borate ester linkages under mild conditions (25 °C, pH ∼ 7.4). This hydrogel had excellent antioxidant abilities due to the 1,4-dihydropyridine (DHP) rings and the vanillin moieties in the hydrogel structures; it was also self-healable and injectable owing to the dynamic borate ester linkages. Furthermore, the antioxidant self-healing hydrogel had low cytotoxicity and exhibited favorable safety in animal experiments, indicating its potential as a safe implantable cell or drug carrier. This study developed a method for preparing functional polymers and related self-healing hydrogels in a facile manner; it demonstrated the value of the Hantzsch reaction in exploiting antioxidant self-healing hydrogels for biomedical applications, which may provide insight into the design of other functional self-healing hydrogels through different multicomponent reactions.

Stimuli-responsive chitosan-based injectable hydrogel for “on-demand” drug release

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Antioxidant Hydrogels: Antioxidant Mechanisms, Design Strategies, and Applications in the Treatment of Oxidative Stress‐Related Diseases

“…using the Hantzsch reaction. [87] The resulting antioxidant PVA exhibited superior therapeutic effects in mucosal repair and wound healing when incorporated into composite hydrogels. Additionally, the Biginelli reaction was employed in the synthesis of innovative antioxidant polymers.…”

Ferrocene-Based Antioxidant Self-Healing Hydrogel via the Biginelli Reaction for Wound Healing

“…Recently, several multicomponent reactions (MCRs), such as the Passerini, Ugi, Biginelli, Kabachnik–Fields, Hantzsch, and Mannich reactions, as well as thiolactone-based and metal-catalyzed MCRs, have been employed to develop novel polymers. − In particular, the Biginelli reaction, which was first introduced in 1891, can efficiently produce antioxidant dihydropyrimidin-2­(H)-one (DHPM) groups using common reactants, such as aldehyde, β-ketoester, and thiourea. The obtained DHPM derivatives can be further modified with new functional groups through nucleophilic reactions, , potentially offering a new means to explore antioxidant self-healing hydrogels.…”