Hydrogel Cross-Linking via Thiol-Reactive Pyridazinediones

TY - JOUR

T1 - Hydrogel Cross-Linking via Thiol-Reactive Pyridazinediones

AU - Spicer, Chris

AU - Grey, William George

AU - Barber, Lydia

AU - Stankevich, Ksenia

AU - Lazarov, Vlado

AU - Kerrigan, Adam

AU - Ramirez Rosales, Angela

N1 - © 2022 The Authors.

PY - 2023/10/4

Y1 - 2023/10/4

N2 - Thiol-reactive Michael acceptors are commonly used for the formation of chemically cross-linked hydrogels. In this paper, we address the drawbacks of many Michael acceptors by introducing pyridazinediones as new cross-linking agents. Through the use of pyridazinediones and their mono- or dibrominated analogues, we show that the mechanical strength, swelling ratio, and rate of gelation can all be controlled in a pH-sensitive manner. Moreover, we demonstrate that the degradation of pyridazinedione-gels can be induced by the addition of thiols, thus providing a route to responsive or dynamic gels, and that monobromo-pyridazinedione gels are able to support the proliferation of human cells. We anticipate that our results will provide a valuable and complementary addition to the existing toolkit of cross-linking agents, allowing researchers to tune and rationally design the properties of biomedical hydrogels.

AB - Thiol-reactive Michael acceptors are commonly used for the formation of chemically cross-linked hydrogels. In this paper, we address the drawbacks of many Michael acceptors by introducing pyridazinediones as new cross-linking agents. Through the use of pyridazinediones and their mono- or dibrominated analogues, we show that the mechanical strength, swelling ratio, and rate of gelation can all be controlled in a pH-sensitive manner. Moreover, we demonstrate that the degradation of pyridazinedione-gels can be induced by the addition of thiols, thus providing a route to responsive or dynamic gels, and that monobromo-pyridazinedione gels are able to support the proliferation of human cells. We anticipate that our results will provide a valuable and complementary addition to the existing toolkit of cross-linking agents, allowing researchers to tune and rationally design the properties of biomedical hydrogels.

U2 - 10.1021/acs.biomac.3c00290

DO - 10.1021/acs.biomac.3c00290

M3 - Article

C2 - 37792488

SN - 1525-7797

JO - Biomacromolecules

JF - Biomacromolecules

ER -