ArticleJournal of medicinal chemistry2013
Sulfated pentagalloylglucoside is a potent, allosteric, and selective inhibitor of factor XIa.
Article in Journal of medicinal chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 51 papers.
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Who cites it
51 citing papers in PubMed, 89 citations in OpenAlex.
- Chemical Synthesis and Biochemical Evaluation of Decasulfated Galloylglucopyranose Heparin Mimetic.Cardiovascular & hematological agents in medicinal chemistry · 2026Article
- New Non-Saccharide Heparin Mimetics as Inhibitors of Cathepsin G.Chemical biology & drug design · 2026Article
- Factor XI inhibitors for the prevention and treatment of venous and arterial thromboembolism.Nature reviews. Cardiology · 2025Review
- The Discovery of a Novel Anticoagulant Mechanism: Factor XI Activation Inhibitors.ACS pharmacology & translational science · 2025Article
- Emerging Targets, Novel Directions, and Innovative Approaches in Thrombosis Therapy.Aging and disease · 2025Review
- A Robust Proteomics-Based Method for Identifying Preferred Protein Targets of Synthetic Glycosaminoglycan Mimetics.bioRxiv : the preprint server for biology · 2025Article
- Sulfonated Penta-galloyl Glucose (SPGG): The Pharmacological Effects of Promiscuous Glycosaminoglycan Small Molecule Mimetic.Mini reviews in medicinal chemistry · 2025Review
- The foundation for investigating factor XI as a target for inhibition in human cardiovascular disease.Journal of thrombosis and thrombolysis · 2024Review
- Article
- Investigation of the anticoagulant activity of cyclic sulfated glycosaminoglycan mimetics.Carbohydrate research · 2023Article
- Homogeneous, Synthetic, Non-Saccharide Glycosaminoglycan Mimetics as Potent Inhibitors of Human Cathepsin G.Biomolecules · 2023Article
- Designing Smaller, Synthetic, Functional Mimetics of Sulfated Glycosaminoglycans as Allosteric Modulators of Coagulation Factors.Journal of medicinal chemistry · 2023Review
- Designing Synthetic, Sulfated Glycosaminoglycan Mimetics That Are Orally Bioavailable and ExhibitingJournal of medicinal chemistry · 2023Article
- Sulphated penta-galloyl glucopyranoside (SPGG) is glycosaminoglycan mimetic allosteric inhibitor of cathepsin G.RPS pharmacy and pharmacology reports · 2023Article
- Expedient Synthesis of a Library of Heparan Sulfate-Like "Head-to-Tail" Linked Multimers for Structure and Activity Relationship Studies.Angewandte Chemie (International ed. in English) · 2022Article
- Physicochemical Properties and Anticoagulant Activity of Purified Heteropolysaccharides fromMolecules (Basel, Switzerland) · 2022Article
- Lignosulfonic Acid Sodium Is a Noncompetitive Inhibitor of Human Factor XIa.Pharmaceuticals (Basel, Switzerland) · 2021Article
- Sulfated Oligomers of Tyrosol: Toward a New Class of Bioinspired Nonsaccharidic Anticoagulants.Biomacromolecules · 2021Article
- Studies on fragment-based design of allosteric inhibitors of human factor XIa.Bioorganic & medicinal chemistry · 2020Article
- Discovery of Benzyl Tetraphosphonate Derivative as Inhibitor of Human Factor Xia.ChemistryOpen · 2020Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
Inhibition of factor XIa (FXIa) is a novel paradigm for developing anticoagulants without major bleeding consequences. We present the discovery of sulfated pentagalloylglucoside (6) as a highly selective inhibitor of human FXIa. Biochemical screening of a focused library led to the identification of 6, a sulfated aromatic mimetic of heparin. Inhibitor 6 displayed a potency of 551 nM against FXIa, which was at least 200-fold more selective than other relevant enzymes. It also prevented activation of factor IX and prolonged human plasma and whole blood clotting. Inhibitor 6 reduced V(MAX) of FXIa hydrolysis of chromogenic substrate without affecting the K(M), suggesting an allosteric mechanism. Competitive studies showed that 6 bound in the heparin-binding site of FXIa. No allosteric small molecule has been discovered to date that exhibits equivalent potency against FXIa. Inhibitor 6 is expected to open up a major route to allosteric FXIa anticoagulants with clinical relevance.
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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.