ArticleJournal of the American Chemical Society2012
Degradable conjugates from oxanorbornadiene reagents.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers, 1 of them a synthesis that pooled it.
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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
22 citing papers in PubMed, 1 synthesis or guideline pooled it, 59 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
- [2.2.1]Heterobicyclic Bromovinyl Sulfones for Thiol-Triggered Strategies in Linker Chemistry: Aza- vs Oxa-Norbornadienic Systems.Bioconjugate chemistry · 2025Article
- Injectable Hydrogels for Programmable Nanoparticle Release.Advanced functional materials · 2025Article
- Experimental and Theoretical Exploration of the Kinetics and Thermodynamics of the Nucleophile-Induced Fragmentation of Ylidenenorbornadiene Carboxylates.The Journal of organic chemistry · 2023Article
- Quantitation of lymphatic transport mechanism and barrier influences on lymph node-resident leukocyte access to lymph-borne macromolecules and drug delivery systems.Drug delivery and translational research · 2021Article
- 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
- Azabicyclic vinyl sulfones for residue-specific dual protein labelling.Chemical science · 2019Article
- Fast, irreversible modification of cysteines through strain releasing conjugate additions of cyclopropenyl ketones.Organic & biomolecular chemistry · 2018Article
- Synthesis and Reactivity of 5-Substituted Furfuryl Carbamates via Oxanorbornadienes.Organic letters · 2017Article
- Efficient Liver Targeting by Polyvalent Display of a Compact Ligand for the Asialoglycoprotein Receptor.Journal of the American Chemical Society · 2017Article
- 1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain.Organic letters · 2016Article
- Albumin-Oxanorbornadiene Conjugates Formed ex Vivo for the Extended Circulation of Hydrophilic Cargo.ACS chemical biology · 2016Article
- Design of Thiol- and Light-sensitive Degradable Hydrogels using Michael-type Addition Reactions.Polymer chemistry · 2015Article
- Modular degradable hydrogels based on thiol-reactive oxanorbornadiene linkers.Journal of the American Chemical Society · 2015Article
- Click chemistry in complex mixtures: bioorthogonal bioconjugation.Chemistry & biology · 2014Review
- Solvent-Free Synthesis and Fluorescence of a Thiol-Reactive Sensor for Undergraduate Organic Laboratories.Journal of chemical education · 2013Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Oxanorbornadienedicarboxylate (OND) reagents were explored for purposes of binding and releasing drugs from serum albumins as representative macromolecular carriers. Being highly reactive Michael acceptors, ONDs form adducts with thiols and amines, which then undergo retro-Diels-Alder fragmentation. A study of more than 30 model adducts revealed a number of modifications that can be used to influence adduct stability. For the most reactive OND linkers, the labeling of the single available bovine serum albumin (BSA) cysteine residue was complete within minutes at a mid-micromolar concentration of reactants. While a selectivity of greater than 1000-fold for thiol over amine was observed with model amino acids, the labeling of protein amines with ONDs is fast enough to be practical, as demonstrated by the reaction with thiol-depleted BSA. The OND-amine adducts were found to be up to 15 times more stable than OND-thiol adducts, and to be sensitive to acid by virtue of a stereochemically dependent acceleration of cycloreversion. The release rate of fluorescent cargo from serum albumins was tuned by selecting the coupling partners: the available half-lives ranged from 40 min to 7 days at 37 °C. Such versatility of release profiles from protein carriers, controlled by the nature of the OND linkage, is a useful addition to the drug delivery toolbox.
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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.