SML0701
GSK-J4
≥98% (HPLC)
Synonym(e):
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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Alle Fotos(1)
About This Item
Empirische Formel (Hill-System):
C24H27N5O2
CAS-Nummer:
Molekulargewicht:
417.50
MDL-Nummer:
UNSPSC-Code:
51111800
PubChem Substanz-ID:
NACRES:
NA.77
Empfohlene Produkte
Qualitätsniveau
Assay
≥98% (HPLC)
Form
powder
Lagerbedingungen
desiccated
Farbe
white to beige
Löslichkeit
DMSO: 20 mg/mL, clear
Lagertemp.
2-8°C
SMILES String
O=C(OCC)CCNC1=CC(N2CCC(C=CC=C3)=C3CC2)=NC(C4=CC=CC=N4)=N1
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)
InChIKey
WBKCKEHGXNWYMO-UHFFFAOYSA-N
Anwendung
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. Wirkung
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
Leistungsmerkmale und Vorteile
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.
Sonstige Hinweise
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.
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Preisangaben
Lagerklassenschlüssel
11 - Combustible Solids
WGK
WGK 3
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
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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)
Cristian Doñas et al.
Journal of autoimmunity, 75, 105-117 (2016-08-17)
As it has been established that demethylation of lysine 27 of histone H3 by the lysine-specific demethylase JMJD3 increases immune responses and thus elicits inflammation, we hypothesize that inhibition of JMJD3 may attenuate autoimmune disorders. We found that in vivo administration
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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
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Staberg M, et al.
Molecular Oncology, 12(3), 406-420 (2018)
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FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 29(11), 4738-4755 (2015-08-01)
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