ArticleBiochemistry2009
A new class of isothiocyanate-based irreversible inhibitors of macrophage migration inhibitory factor.
Article in Biochemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed, 57 citations in OpenAlex.
- Identification of a key water molecule involved in the macrophage migration inhibitory factor-catalyzed tautomerization of para-hydroxyphenylpyruvate using neutron crystallography.Protein science : a publication of the Protein Society · 2026Article
- Using weight loss to predict outcome and define a humane endpoint in preclinical sepsis studies.Scientific reports · 2024Article
- Isothiocyanate-Rich Extracts from Cauliflower (International journal of environmental research and public health · 2022Article
- 7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor.Journal of medicinal chemistry · 2020Article
- Cysteine specific bioconjugation with benzyl isothiocyanates.RSC advances · 2020Article
- A selective small-molecule inhibitor of macrophage migration inhibitory factor-2 (MIF-2), a MIF cytokine superfamily member, inhibits MIF-2 biological activity.The Journal of biological chemistry · 2019Article
- p53 mutant-type in human prostate cancer cells determines the sensitivity to phenethyl isothiocyanate induced growth inhibition.Journal of experimental & clinical cancer research : CR · 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
- Post-translational regulation of macrophage migration inhibitory factor: Basis for functional fine-tuning.Redox biology · 2018Review
- The Fate of a Hapten - From the Skin to Modification of Macrophage Migration Inhibitory Factor (MIF) in Lymph Nodes.Scientific reports · 2018Article
- Macrophage Migration Inhibitory Factor protects cancer cells from immunogenic cell death and impairs anti-tumor immune responses.PloS one · 2018Article
- Physiological relevance of covalent protein modification by dietary isothiocyanates.Journal of clinical biochemistry and nutrition · 2018Review
- Plasma Levels of Macrophage Migration Inhibitory Factor and d-Dopachrome Tautomerase Show a Highly Specific Profile in Early Life.Frontiers in immunology · 2017Article
- Macrophage migration inhibitory factor deficiency enhances immune response to Nippostrongylus brasiliensis.Mucosal immunology · 2017Article
- Identification of Iguratimod as an Inhibitor of Macrophage Migration Inhibitory Factor (MIF) with Steroid-sparing Potential.The Journal of biological chemistry · 2016Article
- Isothiocyanates: a class of bioactive metabolites with chemopreventive potential.Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine · 2015Review
- Limiting cardiac ischemic injury by pharmacological augmentation of macrophage migration inhibitory factor-AMP-activated protein kinase signal transduction.Circulation · 2013Article
- Mechanisms of Nrf2/Keap1-dependent phase II cytoprotective and detoxifying gene expression and potential cellular targets of chemopreventive isothiocyanates.Oxidative medicine and cellular longevity · 2013Review
- Macrophage migration inhibitory factor promotes tumor growth and metastasis by inducing myeloid-derived suppressor cells in the tumor microenvironment.Journal of immunology (Baltimore, Md. : 1950) · 2012Article
Corrections and comments
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Authors and funding
11 authors at 5 institutions in 3 countries.
Funding
Abstract
Macrophage migration inhibitory factor (MIF) is a homotrimeric multifunctional proinflammatory cytokine that has been implicated in the pathogenesis of several inflammatory and autoimmune diseases. Current therapeutic strategies for targeting MIF focus on developing inhibitors of its tautomerase activity or modulating its biological activities using anti-MIF neutralizing antibodies. Herein we report a new class of isothiocyanate (ITC)-based irreversible inhibitors of MIF. Modification by benzyl isothiocyanate (BITC) and related analogues occurred at the N-terminal catalytic proline residue without any effect on the oligomerization state of MIF. Different alkyl and arylalkyl ITCs modified MIF with nearly the same efficiency as BITC. To elucidate the mechanism of action, we performed detailed biochemical, biophysical, and structural studies to determine the effect of BITC and its analogues on the conformational state, quaternary structure, catalytic activity, receptor binding, and biological activity of MIF. Light scattering, analytical ultracentrifugation, and NMR studies on unmodified and ITC-modified MIF demonstrated that modification of Pro1 alters the tertiary, but not the secondary or quaternary, structure of the trimer without affecting its thermodynamic stability. BITC induced drastic effects on the tertiary structure of MIF, in particular residues that cluster around Pro1 and constitute the tautomerase active site. These changes in tertiary structure and the loss of catalytic activity translated into a reduction in MIF receptor binding activity, MIF-mediated glucocorticoid overriding, and MIF-induced Akt phosphorylation. Together, these findings highlight the role of tertiary structure in modulating the biochemical and biological activities of MIF and present new opportunities for modulating MIF biological activities in vivo.
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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.