SML0701
GSK-J4
≥98% (HPLC), jumonji H3K27 demethylase inhibitor, powder
Sinónimos:
Ethyl 3-((6-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2-(pyridin-2-yl)pyrimidin-4-yl)amino)propanoate
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Acerca de este artículo
Fórmula empírica (notación de Hill):
C24H27N5O2
Número CAS:
Peso molecular:
417.50
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Permítanos ayudarleNombre del producto
GSK-J4, ≥98% (HPLC)
SMILES string
O=C(OCC)CCNC1=CC(N2CCC(C=CC=C3)=C3CC2)=NC(C4=CC=CC=N4)=N1
InChI key
WBKCKEHGXNWYMO-UHFFFAOYSA-N
InChI
1S/C24H27N5O2/c1-2-31-23(30)10-14-26-21-17-22(28-24(27-21)20-9-5-6-13-25-20)29-15-11-18-7-3-4-8-19(18)12-16-29/h3-9,13,17H,2,10-12,14-16H2,1H3,(H,26,27,28)
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
Quality Level
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Application
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.
Biochem/physiol Actions
GSK-J4 is a potent selective jumonji H3K27 demethylase inhibitor.
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
To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc
Features and Benefits
GSK-J4 is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit sigma.com/SGC.
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Other Notes
GSK-J4 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the GSK-J4 probe summary on the Chemical Probes Portal website.
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Imane Chakroun et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 29(11), 4738-4755 (2015-08-01)
Adult skeletal muscles can regenerate after injury, due to the presence of satellite cells, a quiescent population of myogenic progenitor cells. Once activated, satellite cells repair the muscle damage by undergoing myogenic differentiation. The myogenic regulatory factors (MRFs) coordinate the
Joseph H Taube et al.
Oncotarget, 8(39), 65548-65565 (2017-10-17)
The deposition of the activating H3K4me3 and repressive H3K27me3 histone modifications within the same promoter, forming a so-called bivalent domain, maintains gene expression in a repressed but transcription-ready state. We recently reported a significantly increased incidence of bivalency following an
Natalia Pediconi et al.
Cell death & disease, 10(7), 518-518 (2019-07-10)
Modification of histones by lysine methylation plays a role in many biological processes, and it is dynamically regulated by several histone methyltransferases and demethylases. The polycomb repressive complex contains the H3K27 methyltransferase EZH2 and controls dimethylation and trimethylation of H3K27
Targeting glioma stem?like cell survival and chemoresistance through inhibition of lysine?specific histone demethylase KDM2B.
Staberg M, et al.
Molecular Oncology, 12(3), 406-420 (2018)
Inhibitor of H3K27 demethylase JMJD3/UTX GSK-J4 is a potential therapeutic option for castration resistant prostate cancer.
Morozov V M, et al.
Oncotarget, 8(37), 62131-62131 (2017)
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