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SML0701

GSK-J4

Name: GSK-J4
Brand: SIGMA

≥98% (HPLC), jumonji H3K27 demethylase inhibitor, powder

Synonym(s):

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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About This Item

Empirical Formula (Hill Notation):

C₂₄H₂₇N₅O₂

CAS Number:

1373423-53-0

Molecular Weight:

417.50

UNSPSC Code:

51111800

PubChem Substance ID:

329825585

NACRES:

NA.77

MDL number:

MFCD22683852

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Product Name

GSK-J4, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

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)

InChI key

WBKCKEHGXNWYMO-UHFFFAOYSA-N

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Related Categories

Bioactive Small Molecules

Structural Genomics Consortium

Protein Biology

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Genome-wide association between Six4, MyoD, and the histone demethylase Utx during myogenesis.

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

The H3K27me3-demethylase KDM6A is suppressed in breast cancer stem-like cells, and enables the resolution of bivalency during the mesenchymal-epithelial transition.

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

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)

EZH2, JMJD3, and UTX epigenetically regulate hepatic plasticity inducing retro-differentiation and proliferation of liver cells.

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

Neuronal activity controls Bdnf expression via Polycomb de-repression and CREB/CBP/JMJD3 activation in mature neurons.

Ernest Palomer et al.

Nature communications, 7, 11081-11081 (2016-03-25)

It has been recently described that in embryonic stem cells, the expression of some important developmentally regulated genes is repressed, but poised for fast activation under the appropriate stimuli. In this work we show that Bdnf promoters are repressed by

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Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Global Trade Item Number

SKU	GTIN
SML0701-5MG	04061832634418
SML0701-25MG	04061832634401

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