| Identification | Back Directory | [Name]
GSK J4 HCl | [CAS]
1373423-53-0 | [Synonyms]
GSK J4
GSK-J4
CS-2143
CS-1667
GSK J4 HCl
6-Triiodophenol
GSK J4 free base
GSKJ4HCL(free base)
GSK J4 HCl USP/EP/BP
GSK J4 HCl (GSKJ4 HCl)
H3K27 histone demethylase inhibitor J4 HCl
Histone Lysine Demethylase Inhibitor VIII, GSK-J4
Histone Lysine Demethylase Inhibitor VIII, GSK-J4 - CAS 1373423-53-0 - Calbiochem
Ethyl 3-((6-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2-(pyridin-2-yl)pyrimidin-4-yl)amino)prop
ethyl 3-[[2-pyridin-2-yl-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)pyrimidin-4-yl]amino]propanoate
N-[2-(2-Pyridinyl)-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyriMidinyl]-|-alanine ethyl ester
Ethyl 3-((6-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2-(pyridin-2-yl)pyrimidin-4-yl)amino)propanoate
β-Alanine, N-[2-(2-pyridinyl)-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyrimidinyl]-, ethyl ester
N-[2-(2-Pyridinyl)-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyrimidinyl]-beta-alanine ethyl ester
β-Alanine, N-[2-(2-pyridinyl)-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyrimidinyl]-, ethyl ester, hydrochloride (1:1) | [Molecular Formula]
C24H27N5O2 | [MDL Number]
MFCD22683852 | [MOL File]
1373423-53-0.mol | [Molecular Weight]
417.5 |
| Chemical Properties | Back Directory | [Boiling point ]
581.2±50.0 °C(Predicted) | [density ]
1.216±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
Tan semi-solid | [pka]
5.95±0.10(Predicted) | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [InChIKey]
WBKCKEHGXNWYMO-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Description]
GSK-J4 (1373423-53-0) is a histone demethylase JMJD3/UTX inhibitor. Inhibits demethylation of histone H3K27. Reduces LPS-induced proinflammatory cytokine production in primary human macrophages (IC50 = 9 μM for the inhibition of TNFα release). Cell permeable, ethyl ester of GSK J1 (cat.# 10-1393).1 GSK-J4 rescues newborn pups from embryonic lethality in BRAF knockin mice which recapitulate major features of RASopathies.2 | [Uses]
GSK-J4 has been used to study the effect of KDM2B (Jumonji (JmjC) domain histone 3 lysine 36 (H3K36) di-demethylase) inhibition on the survival and DNA repair potential of glioblastoma cells. It has also been used in sulforhodamine B (SRB) cell growth assay and cell viability assay. | [Definition]
ChEBI: 3-[[2-(2-pyridinyl)-6-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)-4-pyrimidinyl]amino]propanoic acid ethyl ester is an organonitrogen heterocyclic compound. | [Biochem/physiol Actions]
GSK-J4 is cell permeable prodrug rapidly hydrolysed by macrophage esterases to GSK-J1, a potent selective jumonji H3K27 demethylase inhibitor. Jumonji C domain-containing histone demethylases (JHDMs) are Fe(II) and α-ketoglutarate dependent enzymes that oxygenate methylated histone lysine residues and thereby cause their demethylation. GSK-J1 is selective for the KDM6 subfamily members JMJD3 and UTX with an IC50 of 60 nM in a JMJD3 assay, and is inactive against other demethylases of the JMJ family and over 100 tested kinases and histone deacetylases. The prodrug GSK-J4 inhibited TNF-α production with an IC50 of 9 μM in LPS-stimulated human macrophages and blocked the production of TNF-α by macrophages derived from patients with rheumatoid arthritis. For characterization details for GSK-J4 and full characterization details for GSK-J1, please visit the GSK-J1 probe summary on the Structural Genomics Consortium (SGC) website.To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc | [storage]
Room temperature | [References]
1) Kruidenier et al. (2012), Selective jumonji H3K27 demethylase inhibitor modulates the proinflammatory macrophage response; Nature, 488 404
2) Inoue et al. (2014) New Braf knockin mice provide a pathogenic mechanism of developmental defects and therapeutic approach in cardio-facio-cutaneous syndrome; Hum. Mol. Genet.,?23?6553 |
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