Dataset Information

Reversible cross-linking of gelatin by a disulphide-containing bis-succinimide for tunable degradation and release

ABSTRACT: Highlights • A reversible cross-linker was used to control the cross-linking and degradation of gelatin films.• The cross-linked gelatin films could preserve their morphology in 37 ℃ warm water for above 40 days.• The gelatin film changed its microstructure from net to tightness after the cross-linking.• The degradation of the cross-linked gelatin film could be controlled by glutathione. Generally, gelatin was irreversibly cross-linked by chemical reagents to improve its water-resistance. However, few chemical reagents meet both the requirements of high cross-inking efficiency and tunable degradation. Here a reversible cross-linker, disulphide-containing bis-succinimide, was synthesized and used to control the cross-linking and degradation of edible gelatin film. Mixture of the gelatin and cross-linker for 120 min generated gelatin films that could preserve their morphology in 37 ℃ warm water for above 40 days. The gelatin film changed its microstructure from net to tightness after the cross-linking, thus facilitating the embedding of the targeted molecule into the gelatin material. The degradation of the cross-linked gelatin film and the release of its inclusion could be controlled by biocompatible glutathione. This work provides a good method for preparing modified gelatin with promising water-resistance, good biocompatibility, and tunable degradation for food/biomedical engineering applications.

SUBMITTER:

PROVIDER: S-EPMC10195852 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Similar Datasets

Project description:Reversible covalent conjugation chemistries that allow site- and condition-specific coupling and uncoupling reactions are attractive components in nanotechnologies, bioconjugation methods, imaging, and drug delivery systems. Here, we compare three heterobifunctional cross-linkers, containing both thiol- and amine-reactive chemistries, to form pH-labile hydrazones with hydrazide derivatives of the known and often published water-soluble polymer, poly[N-(2-hydroxypropyl methacrylamide)] (pHPMA), while subsequently coupling thiol-containing molecules to the cross-linker via maleimide addition. Two novel cross-linkers were prepared from the popular heterobifunctional cross-linking agent, succinimidyl-4-(N-maleimidomethyl) cyclohexane-1-carboxylate (SMCC), modified to contain either terminal aldehyde groups (i.e., 1-(N-3-propanal)-4-(N-maleimidomethyl) cyclohexane carboxamide, PMCA) or methylketone groups (i.e., 1-(N-3-butanone)-4-(N-maleimidomethyl) cyclohexane carboxamide, BMCA). A third cross-linking agent was the commercially available N-4-acetylphenyl maleimide (APM). PMCA and BMCA exhibited excellent reactivity toward hydrazide-derivatized pHPMA with essentially complete hydrazone conjugation to polymer reactive sites, while APM coupled only ∼60% of available reactive sites on the polymer despite a 3-fold molar excess relative to polymer hydrazide groups. All polymer hydrazone conjugates bearing these bifunctional agents were then further reacted with thiol-modified tetramethylrhodamine dye, confirming cross-linker maleimide reactivity after initial hydrazone polymer conjugation. Incubation of dye-labeled polymer conjugates in phosphate buffered saline at 37 °C showed that hydrazone coupling resulting from APM exhibited the greatest difference in stability between pH 7.4 and 5.0, with hydrolysis and dye release increased at pH 5.0 over a 24 h incubation period. Polymer conjugates bearing hydrazones formed from cross-linker BMCA exhibited intermediate stability with hydrolysis much greater at pH 5.0 at early time points, but hydrolysis at pH 7.4 was significant after 5 h. Hydrazones formed with the PMCA cross-linker showed no difference in release rates at pH 7.4 and 5.0.

Dataset Information

Reversible cross-linking of gelatin by a disulphide-containing bis-succinimide for tunable degradation and release

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets