ArticleChemical communications (Cambridge, England)2018
Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs.
Article in Chemical communications (Cambridge, England), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Click-to-Release Reactions for Tertiary Amines and Pyridines.Journal of the American Chemical Society · 2026Article
- Bioactive Sulfonamides Derived from Amino Acids: Their Synthesis and Pharmacological Activities.Mini reviews in medicinal chemistry · 2025Review
- Sydnthiones are versatile bioorthogonal hydrogen sulfide donors.Nature communications · 2024Article
- Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors.Molecules (Basel, Switzerland) · 2021Review
- Bioorthogonal Reactions of Triarylphosphines and Related Analogues.Chemical reviews · 2021Review
- Gold-Based Pharmacophore Inhibits Intracellular MYC Protein.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs.Molecules (Basel, Switzerland) · 2020Review
- Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.Journal of the American Chemical Society · 2020Article
- Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups.Chemical science · 2020Article
- Developing bioorthogonal probes to span a spectrum of reactivities.Nature reviews. Chemistry · 2020Article
- Isomeric triazines exhibit unique profiles of bioorthogonal reactivity.Chemical science · 2019Article
- Stable, Reactive, and Orthogonal Tetrazines: Dispersion Forces Promote the Cycloaddition with Isonitriles.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.
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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.