ArticleJournal of the American Chemical Society2016
A Fluorescence Polarization Assay for Binding to Macrophage Migration Inhibitory Factor and Crystal Structures for Complexes of Two Potent Inhibitors.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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The trial behind it
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Who cites it
23 citing papers in PubMed, 46 citations in OpenAlex.
- MIF tautomerase inhibitor 4-IPP alleviates HFD-induced obesity by restoring CD137-mediated browning of white adipocytes in mice.Acta pharmacologica Sinica · 2026Article
- Rational Design of Stapled Covalent Peptide Modifiers of Oncoprotein E6 from Human Papillomavirus.ACS chemical biology · 2025Article
- Macrophage migration inhibitory factor (MIF) in CNS diseases: Functional regulation and potential therapeutic indication.Fundamental research · 2024Review
- Automated Adaptive Absolute Binding Free Energy Calculations.Journal of chemical theory and computation · 2024Article
- Comparison of Receptor-Ligand Restraint Schemes for Alchemical Absolute Binding Free Energy Calculations.Journal of chemical theory and computation · 2023Article
- Discovery of novel MIF inhibitors that attenuate microglial inflammatory activation by structures-based virtual screening and in vitro bioassays.Acta pharmacologica Sinica · 2022Article
- 4-Iodopyrimidine Labeling Reveals Nuclear Translocation and Nuclease Activity for Both MIF and MIF2.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Immune cell infiltration and the genes associated with ligamentum flavum hypertrophy: Identification and validation.Frontiers in cell and developmental biology · 2022Article
- Bifunctional small molecules that mediate the degradation of extracellular proteins.Nature chemical biology · 2021Article
- Proteolysis Targeting Chimera (PROTAC) for Macrophage Migration Inhibitory Factor (MIF) Has Anti-Proliferative Activity in Lung Cancer Cells.Angewandte Chemie (International ed. in English) · 2021Article
- Designed CXCR4 mimic acts as a soluble chemokine receptor that blocks atherogenic inflammation by agonist-specific targeting.Nature communications · 2020Article
- Explicit Representation of Cation-π Interactions in Force Fields with 1/Journal of chemical theory and computation · 2020Article
- 7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor.Journal of medicinal chemistry · 2020Article
- Inhibition of Macrophage Migration Inhibitory Factor by a Chimera of Two Allosteric Binders.ACS medicinal chemistry letters · 2020Article
- Absolute Free Energy of Binding Calculations for Macrophage Migration Inhibitory Factor in Complex with a Druglike Inhibitor.The journal of physical chemistry. B · 2019Article
- Small-molecule inhibitors of macrophage migration inhibitory factor (MIF) as an emerging class of therapeutics for immune disorders.Drug discovery today · 2018Review
- Advances and Insights for Small Molecule Inhibition of Macrophage Migration Inhibitory Factor.Journal of medicinal chemistry · 2018Article
- Optimization of Pyrazoles as Phenol Surrogates to Yield Potent Inhibitors of Macrophage Migration Inhibitory Factor.ChemMedChem · 2018Article
- π-Cation Interactions in Molecular Recognition: Perspectives on Pharmaceuticals and Pesticides.Journal of agricultural and food chemistry · 2018Review
- Discovery of chromenes as inhibitors of macrophage migration inhibitory factor.Bioorganic & medicinal chemistry · 2018Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Human macrophage migration inhibitory factor (MIF) is both a keto-enol tautomerase and a cytokine associated with numerous inflammatory diseases and cancer. Consistent with observed correlations between inhibition of the enzymatic and biological activities, discovery of MIF inhibitors has focused on monitoring the tautomerase activity using l-dopachrome methyl ester or 4-hydroxyphenyl pyruvic acid as substrates. The accuracy of these assays is compromised by several issues including substrate instability, spectral interference, and short linear periods for product formation. In this work, we report the syntheses of fluorescently labeled MIF inhibitors and their use in the first fluorescence polarization-based assay to measure the direct binding of inhibitors to the active site. The assay allows the accurate and efficient identification of competitive, noncompetitive, and covalent inhibitors of MIF in a manner that can be scaled for high-throughput screening. The results for 22 compounds show that the most potent MIF inhibitors bind with Kd values of ca. 50 nM; two are from our laboratory, and the other is a compound from the patent literature. X-ray crystal structures for two of the most potent compounds bound to MIF are also reported here. Striking combinations of protein-ligand hydrogen bonding, aryl-aryl, and cation-π interactions are responsible for the high affinities. A new chemical series was then designed using this knowledge to yield two more strong MIF inhibitors/binders.
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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.