ArticleJournal of the American Chemical Society2023
Sulfamate Acetamides as Self-Immolative Electrophiles for Covalent Ligand-Directed Release Chemistry.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 37 citations in OpenAlex.
- Chemical reactions for the ligand-directed modification of native proteins.Chemical Society reviews · 2026Review
- Progress and challenges in traceless ligand-directed labelling chemistry.Communications chemistry · 2026Review
- Recent advances in site-specific modifications of peptides and proteins.Chemical science · 2026Review
- α-Halothioamide warheads with enhanced cysteine reactivity and specificity for covalent protein labelling.Nature communications · 2026Article
- Discovery of New OTUB1 Covalent Ligands via Structure-Activity Relationship Studies for Targeted Protein Stabilization.Journal of medicinal chemistry · 2026Article
- Attempts to Achieve Targeted Covalent Inhibition of Hsp90β.Chemical biology & drug design · 2026Article
- Tunable Aromatic Sulfoxides and Sulfones as Cysteine-Targeting Warheads: Exploring the Structure-Reactivity Relationship.Journal of medicinal chemistry · 2026Article
- Lysine Targeting Group-Transfer Chimeras for Proximity Induction.Angewandte Chemie (International ed. in English) · 2026Article
- Modular Vinyl Phosphonamidates for Cysteine-Directed Protein Targeting.Journal of the American Chemical Society · 2026Article
- Exploiting intracellular oncogenic proteins to release cytotoxins.RSC medicinal chemistry · 2026Article
- Shaping Antimalarials: A Geometry-First Approach toJournal of medicinal chemistry · 2026Article
- Developments and challenges in hit progression within fragment-based drug discovery.Nature communications · 2026Review
- Article
- Template-Based Docking Using Automated Maximum Common Substructure Identification with EnzyDock: Mechanistic and Inhibitor Docking.Journal of chemical information and modeling · 2025Article
- Total syntheses of cyclohelminthol I-IV reveal a new cysteine-selective covalent reactive group.Chemical science · 2025Article
- Chemoselective Stabilized Triphenylphosphonium Probes for Capturing Reactive Carbonyl Species and Regenerating Covalent Inhibitors with Acrylamide Warheads in Cellulo.Journal of the American Chemical Society · 2025Article
- Covalent Proximity Inducers.Chemical reviews · 2025Review
- Extrapolating Lessons from Targeted Protein Degradation to Other Proximity-Inducing Drugs.ACS chemical biology · 2024Review
- Electrophilic Compounds in the Human Diet and Their Role in the Induction of the Transcription Factor NRF2.International journal of molecular sciences · 2024Review
- Using a Function-First "Scout Fragment"-Based Approach to Develop Allosteric Covalent Inhibitors of Conformationally Dynamic Helicase Mechanoenzymes.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
21 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Electrophiles for covalent inhibitors that are suitable for in vivo administration are rare. While acrylamides are prevalent in FDA-approved covalent drugs, chloroacetamides are considered too reactive for such purposes. We report sulfamate-based electrophiles that maintain chloroacetamide-like geometry with tunable reactivity. In the context of the BTK inhibitor ibrutinib, sulfamate analogues showed low reactivity with comparable potency in protein labeling, in vitro, and cellular kinase activity assays and were effective in a mouse model of CLL. In a second example, we converted a chloroacetamide Pin1 inhibitor to a potent and selective sulfamate acetamide with improved buffer stability. Finally, we show that sulfamate acetamides can be used for covalent ligand-directed release (CoLDR) chemistry, both for the generation of "turn-on" probes as well as for traceless ligand-directed site-specific labeling of proteins. Taken together, this chemistry represents a promising addition to the list of electrophiles suitable for in vivo covalent targeting.
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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.