ArticleJournal of the American Chemical Society2015
Modular degradable hydrogels based on thiol-reactive oxanorbornadiene linkers.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers, 1 of them a synthesis that pooled it.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
17 citing papers in PubMed, 1 synthesis or guideline pooled it, 35 citations in OpenAlex.
- Lymphatic immunomodulation using engineered drug delivery systems for cancer immunotherapy.Advanced drug delivery reviews · 2020Pooled it
- Tunable Linkers for Dynamic Thiol-Based Bioconjugation Strategies.Biomacromolecules · 2026Review
- Development of Bioorthogonally Degradable Tough Hydrogels Using Enamine N-Oxide Based Crosslinkers.Advanced materials (Deerfield Beach, Fla.) · 2025Article
- Injectable Hydrogels for Programmable Nanoparticle Release.Advanced functional materials · 2025Article
- Extracellular vesicle biopotentiated hydrogels for diabetic wound healing: The art of living nanomaterials combined with soft scaffolds.Materials today. Bio · 2023Review
- Experimental and Theoretical Exploration of the Kinetics and Thermodynamics of the Nucleophile-Induced Fragmentation of Ylidenenorbornadiene Carboxylates.The Journal of organic chemistry · 2023Article
- The Influence of Substitution on Thiol-Induced Oxanorbornadiene Fragmentation.Organic letters · 2021Article
- Azanorbornadienes as Thiol-Reactive Cleavable Linkers.Organic letters · 2020Article
- Degradable Hydrogels for the Delivery of Immune-modulatory Proteins in the Wound Environment.ACS applied bio materials · 2020Article
- Programmable multistage drug delivery to lymph nodes.Nature nanotechnology · 2020Article
- Assembly of (l+d)-Tryptophan Derivatives Containing an Imidazole Group Selectively Forms a Rare Purple NiChemistryOpen · 2019Article
- Fast, irreversible modification of cysteines through strain releasing conjugate additions of cyclopropenyl ketones.Organic & biomolecular chemistry · 2018Article
- Recent advances of on-demand dissolution of hydrogel dressings.Burns & trauma · 2018Review
- Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes.Organic letters · 2017Article
- In Situ-Forming Polyamidoamine Dendrimer Hydrogels with Tunable Properties Prepared via Aza-Michael Addition Reaction.ACS applied materials & interfaces · 2017Article
- Hierarchical Assembly of Bioactive Amphiphilic Molecule Pairs into Supramolecular Nanofibril Self-Supportive Scaffolds for Stem Cell Differentiation.Journal of the American Chemical Society · 2016Article
- Albumin-Oxanorbornadiene Conjugates Formed ex Vivo for the Extended Circulation of Hydrophilic Cargo.ACS chemical biology · 2016Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Oxanorbornadiene dicarboxylate (OND) reagents are potent Michael acceptors, the adducts of which undergo fragmentation by retro-Diels-Alder reaction at rates that vary with the substitution pattern on the OND moiety. Rapid conjugate addition between thiol-terminated tetravalent PEG and multivalent ONDs yielded self-supporting hydrogels within 1 min at physiological temperature and pH. Erosion of representative hydrogel formulations occurred with predictable and pH-independent rates on the order of minutes to weeks. These materials could be made non-degradable by epoxidation of the OND linkers without slowing gelation. Hydrogels prepared with OND linkers of equal valence had comparable physical properties, as determined by equilibrium swelling behavior, indicating similar internal network structure. Diffusion and release of entrained cargo varied with both the rate of degradation of PEG-OND hydrogels and the hydrodynamic radius of the entrained species. These results highlight the utility of OND linkers in the preparation of degradable network materials with potential applications in sustained release.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.