JIB-04Jumonji histone demethylase inihibitor CAS# 199596-05-9 |
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Quality Control & MSDS
3D structure
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| Cas No. | 199596-05-9 | SDF | Download SDF |
| PubChem ID | 6519698 | Appearance | Powder |
| Formula | C17H13ClN4 | M.Wt | 308.76 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 100 mg/mL (323.88 mM; ultrasonic and adjust pH to 2 with 1M HCl) Ethanol : 2 mg/mL (6.48 mM; Need ultrasonic) | ||
| Chemical Name | 5-chloro-N-[(E)-[phenyl(pyridin-2-yl)methylidene]amino]pyridin-2-amine | ||
| SMILES | C1=CC=C(C=C1)C(=NNC2=NC=C(C=C2)Cl)C3=CC=CC=N3 | ||
| Standard InChIKey | YHHFKWKMXWRVTJ-OQKWZONESA-N | ||
| Standard InChI | InChI=1S/C17H13ClN4/c18-14-9-10-16(20-12-14)21-22-17(13-6-2-1-3-7-13)15-8-4-5-11-19-15/h1-12H,(H,20,21)/b22-17+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Pan Jumonji histone demethylase inhibitor (IC50 values are 230, 340, 435, 445, 855 and 1100 nM for JARID1A, JMJD2E, JMJD2B, JMJD2A, JMJD3 and JMJD2C respectively). Exhibits negligible activity at PHD2 and TET1. Selectively blocks cancer cell growth in vitro and diminishes tumor growth in H358 and A549 mouse xenograft models in vivo. Prolongs survival in a mouse model of breast cancer. |
JIB-04 Dilution Calculator
JIB-04 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.2388 mL | 16.1938 mL | 32.3876 mL | 64.7752 mL | 80.969 mL |
| 5 mM | 0.6478 mL | 3.2388 mL | 6.4775 mL | 12.955 mL | 16.1938 mL |
| 10 mM | 0.3239 mL | 1.6194 mL | 3.2388 mL | 6.4775 mL | 8.0969 mL |
| 50 mM | 0.0648 mL | 0.3239 mL | 0.6478 mL | 1.2955 mL | 1.6194 mL |
| 100 mM | 0.0324 mL | 0.1619 mL | 0.3239 mL | 0.6478 mL | 0.8097 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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JIB-04 is a small molecule inhibitor of Jumonji histone demethylase with IC50 values of [1].
JIB-04 is a pyridine hydrazone. It is a pan -selective inhibitor of Jumonji histone demethylases. In a sensitive ELISA assay, JIB-04 inhibits JARID1A, JMJD2A, JMJD2B, JMJD2C, JMJD2E and JMJD3 with IC50 values of 230nM, 445nM, 435nM, 1100nM, 340nM and 855nM, respectively. Among the JMJD2 (KDM4) subfamily, JMJD2D has highest sensitivity. JIB-04 inhibits Jumonji demethylases in a unique manner. It is found not to be a competitive inhibitor of α-ketoglutarate in the competition assay [1].
JIB-04 shows consistently selective for cancer cells over normal cells. It has efficacy in cultured lung and prostate cancer lines with IC50 values as low as 10nM. JIB-04 is also effective in controlling lung cancer growth in animals. It significantly suppresses tumor growth of H358 and A549 lung cancer cell xenografts in mice with IC50 values of 100nM and 250nM, respectively. Furthermore, the anti-proliferation activity of JIB-04 results in a reduction in cancer-induced death rates in mice [1].
References:
[1] Wang L, Chang J, Varghese D, Dellinger M, Kumar S, Best AM, Ruiz J, Bruick R, Peña-Llopis S, Xu J, Babinski DJ, Frantz DE, Brekken RA, Quinn AM, Simeonov A, Easmon J, Martinez ED. A small molecule modulates Jumonji histone demethylase activity and selectively inhibits cancer growth. Nat Commun. 2013;4:2035.
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The small molecule JIB-04 disrupts O2 binding in the Fe-dependent histone demethylase KDM4A/JMJD2A.[Pubmed:28144654]
Chem Commun (Camb). 2017 Feb 9;53(13):2174-2177.
JIB-04, a specific inhibitor of the O2-activating, Fe-dependent histone lysine demethylases, is revealed to disrupt the binding of O2 in KDM4A/JMJD2A through a continuous O2-consumption assay, X-ray crystal structure data, and molecular docking.
A small molecule modulates Jumonji histone demethylase activity and selectively inhibits cancer growth.[Pubmed:23792809]
Nat Commun. 2013;4:2035.
The pharmacological inhibition of general transcriptional regulators has the potential to block growth through targeting multiple tumorigenic signalling pathways simultaneously. Here, using an innovative cell-based screen, we identify a structurally unique small molecule (named JIB-04) that specifically inhibits the activity of the Jumonji family of histone demethylases in vitro, in cancer cells, and in tumours in vivo. Unlike known inhibitors, JIB-04 is not a competitive inhibitor of alpha-ketoglutarate. In cancer, but not in patient-matched normal cells, JIB-04 alters a subset of transcriptional pathways and blocks viability. In mice, JIB-04 reduces tumour burden and prolongs survival. Importantly, we find that patients with breast tumours that overexpress Jumonji demethylases have significantly lower survival. Thus, JIB-04, a novel inhibitor of Jumonji demethylases in vitro and in vivo, constitutes a unique potential therapeutic and research tool against cancer, and validates the use of unbiased cellular screens to discover chemical modulators with disease relevance.
Azinyl and diazinyl hydrazones derived from aryl N-heteroaryl ketones: synthesis and antiproliferative activity.[Pubmed:9435912]
J Med Chem. 1997 Dec 19;40(26):4420-5.
A series of N-heteroaryl hydrazones derived from aryl N-heteroaryl or bis-N-heteroaryl methanones was prepared in search for potential novel antitumor agents. The stereochemistry of these compounds was established by means of NMR spectroscopy. Antiproliferative activity was determined in a panel of human tumor cell lines (CCRF-CEM, Burkitt's lymphoma, HeLa, ZR-75-1, HT-29, and MEXF 276L) in vitro. Generally, the new compounds were found to be more potent (IC50 = 0.011-0.436 microM) than the ribonucleotide reductase inhibitor hydroxyurea (IC50 = 140 microM). Most of the compounds exhibited the highest activity against Burkitt's lymphoma with an IC50 of 0.011-0.035 microM. [14C]Cytidine incorporation into DNA was quantitated for selected hydrazones (Z-A, E-1, Z-3, Z-4, E-5, Z-5, E-13, E-18, Z-19, Z-24, and E-26) as a measure of the inhibition of ribonucleotide reductase in Burkitt's lymphoma cells. The E-configurated compounds were found to inhibit [14C]cytidine incorporation to a greater extent (IC50 = 0.67-5.05 microM) than the Z-isomers (IC50 = 7.20 to > 10 microM). Principal component analysis of the IC50 values obtained for inhibition of cell proliferation revealed that the cell lines tested can be grouped into three main families showing different sensitivities toward the compounds in our series [(i) CCRF-CEM, Burkitt's lymphoma, and Hela; (ii) HT-29; and (iii) MEXF 276 L].
