ChEMBL ligand: CHEMBL210858
histone deacetylase 6/Histone deacetylase 6 in Human [ChEMBL: CHEMBL1865] [GtoPdb: 2618] [UniProtKB: Q9UBN7] There should be some charts here, you may need to enable JavaScript!
Macrophage migration inhibitory factor in Human [ChEMBL: CHEMBL2085] [UniProtKB: P14174] Macrophage migration inhibitory factor in Mouse [ChEMBL: CHEMBL1926491] [UniProtKB: P34884] Macrophage migration inhibitory factor in Rat [ChEMBL: CHEMBL4524037] [UniProtKB: P30904] There should be some charts here, you may need to enable JavaScript!
sigma non-opioid intracellular receptor 1/Sigma non-opioid intracellular receptor 1 in Rat [ChEMBL: CHEMBL3602] [GtoPdb: 2552] [UniProtKB: Q9R0C9] There should be some charts here, you may need to enable JavaScript!

DB	Assay description	Assay Type	Standard value	Standard parameter	Original value	Original units	Original parameter	Reference
histone deacetylase 6/Histone deacetylase 6 in Human (target type: SINGLE PROTEIN) [ChEMBL: CHEMBL1865] [GtoPdb: 2618] [UniProtKB: Q9UBN7]
ChEMBL	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 with custom peptide substrate	B	6.01	pIC50	985.7	nM	IC50	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
Macrophage migration inhibitory factor in Human (target type: SINGLE PROTEIN) [ChEMBL: CHEMBL2085] [UniProtKB: P14174]
ChEMBL	Displacement of 4'-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-[1,1'-biphenyl]-4-carboxylic acid from C-terminal His-tagged recombinant human MIF expressed in Escherichia coli BL21 (DE3) preincubated for 10 mins followed by probe addition and measured after 10 mins by fluorescence assay	B	4.33	pKd	47000	nM	Kd	J Med Chem (2020) 63: 11920-11933 [PMID:32940040]
ChEMBL	Inhibition of C-terminal His-tagged recombinant human MIF expressed in Escherichia coli BL21 (DE3) using 4-HPP as substrate preincubated for 10 mins followed by substrate addition by UV absorption spectrum analysis	B	4.36	pKi	44000	nM	Ki	J Med Chem (2020) 63: 11920-11933 [PMID:32940040]
ChEMBL	Inhibition of C-terminal His-tagged recombinant human MIF tautomerase activity expressed in Escherichia coli BL21 using 4-hydroxyphenyl pyruvic acid as substrate preincubated for 15 mins followed by substrate addition and measured for 10 mins in presence of 0.5 mM EDTA by UV absorbance based Cheng-Prusoff equation analysis	B	4.36	pKi	44000	nM	Ki	Eur J Med Chem (2020) 186: 111849-111849 [PMID:31767137]
ChEMBL	Inhibition of MIF tautomerase (unknown origin) using 4-HPP as substrate preincubated for 1 hr followed by substrate addition by Lineweaver-Burk plot anlysis	B	4.36	pKi	43500	nM	Ki	Bioorg Med Chem Lett (2022) 55: 128445-128445 [PMID:34758374]
ChEMBL	Inhibition of Tautomerase Activity of Human MIF: Inhibition of the tautomerase activity of MIF was measured using 4-hydroxyphenyl pyruvic acid (HPP) as substrate, largely following previously reported protocols (Taylor et al., Biochemistry, 1999, 38, 7444-7452). HPP was dissolved in 0.5 M acetate buffer, pH 6.0 to a final concentration of 10 mM and incubated overnight at room temperature to allow equilibration of the keto and enol forms. MIF (6 μL) was premixed in 500 mM boric acid, pH 6.2 (142 μL) and transferred to a transparent U bottom 96-well plate to a final concentration of 50 nM MIF. At this concentration high signal-to-noise and linearity were observed after analysis of progress curves for enol production at different protein concentrations. Inhibitors were dissolved in DMSO to 10 mM and an initial screen was performed. For compounds that showed ca. 25% or greater inhibition at 10 μM, an inhibition constant, was measured.Compounds were placed into wells (2 μL) at 6 different concentrations and incubated for 30 minutes until the assay was started by addition of HPP (504) at two concentrations (1.0 and 2.5 mM). The negative control was MIF incubated with DMSO vehicle, which in all assays was 1% and did not influence tautomerase activity. MIF activity was monitored at 305 nm for formation of the borate-enol complex using an Infinite F500 plate reader (TECAN, Morrisville, N.C.) for 175 seconds. Calculation of initial velocities and the nonlinear regression analyses for the enzyme kinetics were repeated three times with the program Prism6 (GraphPad, La Jolla, Calif.).Data obtained for the Example compounds, obtained using the methods described in Example B, are provided in Table 3. Results are also included for a reference compound ISO-1 (Chang, K. F.; Al-Abed, Y. Bioorg. Med. Chem. Lett. 2006, 16, 3376-3379; Balachandran, S. et al. Bioorg. Med. Chem. Lett. 2009, 19, 4773-4776). X-ray crystal structures were obtained for complexes of 3a, 3b, and 3v (Examples 1, 2, and 21) with human MIF as described below in Example C, which confirm the binding of these inhibitors in the tautomerase active site.	B	4.68	pKi	21000	nM	Ki	US-10336721-B2. Biaryltriazole inhibitors of macrophage migration inhibitory factor (2019)
ChEMBL	Inhibition Assay: Data obtained for the Example compounds, obtained using the methods described in Example B.	B	4.68	pKi	21000	nM	Ki	US-10968198-B2. Biaryltriazole inhibitors of macrophage migration inhibitory factor (2021)
ChEMBL	Inhibition of dopachrome tautomerase activity of human recombinant MIF	B	4	pIC50	>100000	nM	IC50	Bioorg Med Chem Lett (2009) 19: 4773-4776 [PMID:19592246]
ChEMBL	Inhibition of [3H]-BTZO-1 binding to recombinant human C-terminal His-tagged MIF expressed in Escherichia coli BL21 (DE3) measured after 3 hrs by SPA	B	4	pIC50	>100000	nM	IC50	Chem Biol (2010) 17: 1282-1294 [PMID:21168764]
ChEMBL	Inhibition of recombinant His-tagged MIF tautomerase activity (unknown origin) using 4-HPP as substrate	B	4.1	pIC50	79000	nM	IC50	Bioorg Med Chem (2018) 26: 999-1005 [PMID:29428527]
ChEMBL	Inhibition of dopachrome tautomerase activity of MIF in human THP1 cells	B	4.16	pIC50	69000	nM	IC50	Bioorg Med Chem Lett (2009) 19: 4773-4776 [PMID:19592246]
ChEMBL	Inhibition of MIF tautomerase (unknown origin) using 4-HPP as substrate preincubated for 1 hr followed by substrate addition	B	4.19	pIC50	65300	nM	IC50	Bioorg Med Chem Lett (2022) 55: 128445-128445 [PMID:34758374]
ChEMBL	Inhibition of C-terminal His-tagged recombinant human MIF tautomerase activity expressed in Escherichia coli BL21 using 4-hydroxyphenyl pyruvic acid as substrate preincubated for 15 mins followed by substrate addition and measured for 10 mins in presence of 0.5 mM EDTA by UV absorbance analysis	B	4.19	pIC50	64000	nM	IC50	Eur J Med Chem (2020) 186: 111849-111849 [PMID:31767137]
ChEMBL	Inhibition of spontaneous secretion/release/recognition of MIF from freshly isolated human PBMC by ELISA	B	4.6	pIC50	25000	nM	IC50	Bioorg Med Chem Lett (2009) 19: 4773-4776 [PMID:19592246]
ChEMBL	Inhibition of recombinant human MIF (Pro2 to Ala115 residues) expressed in Escherichia coli using dopachrome methyl ester as substrate preincubated with protein followed by substrate addition	B	4.74	pIC50	18200	nM	IC50	J Med Chem (2018) 61: 8104-8119 [PMID:29812929]
ChEMBL	Inhibition of MIF tautomerase activity	B	4.96	pIC50	11000	nM	IC50	Bioorg Med Chem Lett (2006) 16: 3376-3379 [PMID:16682188]
ChEMBL	Inhibition of recombinant MIF (unknown origin) tautomerase activity using dopachrome methyl ester as substrate measured for 2 to 20 secs by spectrophotometric analysis	B	5.15	pIC50	7000	nM	IC50	J Med Chem (2018) 61: 8104-8119 [PMID:29812929]
Macrophage migration inhibitory factor in Mouse (target type: SINGLE PROTEIN) [ChEMBL: CHEMBL1926491] [UniProtKB: P34884]
ChEMBL	Enzyme Assay: MIF tautomerase activity was measured by UV-Visible recording spectrophotometry (SHIMADZU, UV1600U). A fresh stock solution of L-dopachrome methyl ester was prepared at 2.4 mM through oxidation of L-3,4-dihydroxyphenylalanine methyl ester with sodium periodate. 1 μL of MIF solution (800-900 ng/mL) and 1 μL of a DMSO solution with various concentrations of the enzymatic inhibitor were added into a plastic cuvette (10 mm, 1.5 mL) containing 0.7 mL assay buffer (50 mM potassium phosphate, pH 7.2). Then L-dopachrome methyl ester solution (0.3 mL) was added to the assay buffer mixture. Activity was determined at room temperature and the spectrometric measurements were made at λ=475 nm for 20 seconds by monitoring the rate of decolorization of L-dopachrome methyl ester in comparison to a standard solution.	B	4.96	pIC50	11000	nM	IC50	US-8618147-B2. Modified macrophage migration inhibitory factor inhibitors (2013)
Macrophage migration inhibitory factor in Rat (target type: SINGLE PROTEIN) [ChEMBL: CHEMBL4524037] [UniProtKB: P30904]
ChEMBL	Inhibition of recombinant rat MIF expressed in Escherichia coli BL21 (DE3) assessed as reduction in tautomerase activity using L-dopachrome carboxy-methyl ester as substrate by spectrophotometry	B	4.17	pIC50	68000	nM	IC50	Chem Biol (2010) 17: 1282-1294 [PMID:21168764]
sigma non-opioid intracellular receptor 1/Sigma non-opioid intracellular receptor 1 in Rat (target type: SINGLE PROTEIN) [ChEMBL: CHEMBL3602] [GtoPdb: 2552] [UniProtKB: Q9R0C9]
ChEMBL	Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in rat brain by competition binding assay	B	6.99	pKi	102.3	nM	Ki	Medchemcomm (2015) 6: 1093-1103

ChEMBL data shown on this page come from version 36:

Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR. (2024). The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res., 52(D1). DOI: 10.1093/nar/gkad1004. [EPMCID:10767899] [PMID:37933841]
Davies M, Nowotka M, Papadatos G, Dedman N, Gaulton A, Atkinson F, Bellis L, Overington JP. (2015) 'ChEMBL web services: streamlining access to drug discovery data and utilities.' Nucleic Acids Res., 43(W1). DOI: 10.1093/nar/gkv352. [EPMCID:25883136]