Prodrug of a selective H3K27 histone demethylase inhibitor
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Active Metabolite(s)
12054GSK-J1 (sodium salt)
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GSK-J4 (hydrochloride)

Item No. 12073

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(2-pyridinyl)-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyrimidinyl]-β-alanine, ethyl ester, monohydrochloride
CAS Number
1797983-09-5
Molecular Formula
C24H27N5O2 • HCl
Formula Weight
454.0
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:7): 0.1 mg/mlEthanol: 20 mg/ml
λmax
260 nm
SMILES
O=C(OCC)CCNC1=CC(N2CCC(C=CC=C3)=C3CC2)=NC(C4=CC=CC=N4)=N1.Cl
InChi Code
InChI=1S/C24H27N5O2.ClH/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);1H
InChi Key
TYXWLTBYINKVNT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    The histone H3 lysine 27 (H3K27) demethylase JMJD3 plays important roles in the transcriptional regulation of cell differentiation, development, the inflammatory response, and cancer.1,2 GSK-J4 (hydrochloride) is an ethyl ester derivative of the JMJD3 selective histone demethylase inhibitor GSK-J1 (Item No. 12054) with an IC50 value greater than 50 μM in vitro.3 Acting as a prodrug, GSK-J4 is rapidly hydrolyzed in cells to the otherwise cell impermeable GSK-J1, which exhibits an IC50 value of 60 nM for the purified enzyme. When administered to human primary macrophages, GSK-J4 can reduce LPS-induced proinflammatory cytokine production, most notably including that of TNFα (IC50 = 9 µM).3 See the Structural Genomics Consortium (SGC) website for more information.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Agger, K., Cloos, P.A.C., Christensen, J., et al. UTX and JMJD3 are histone H3K27 demethylases involved in HOX gene regulation and development. Nature 449(7163), 731-734 (2011).

    2. Hübner, M.R., and Spector, D.L. Role of H3K27 demethylases Jmjd3 and UTX in transcriptional regulation. Cold Spring Harb. Symp. Quant. Biol. 75, 43-49 (2010).

    3. Kruidenier, L., Chung, C.W., Cheng, Z., et al. A selective jumonji H3K27 demethylase inhibitor modulates the proinflammatory macrophage response. Nature 488(7411), 404-408 (2012).

    Product Citations

    Yang, B., Alimperti, S., Gonzalez, M.V., et al. Reepithelialization of diabetic skin and mucosal wounds is rescued by treatment with epigenetic inhibitors. Diabetes 73(1), 120-134 (2024).

    Burgess, S.L., Saleh, M., Cowardin, C.A., et al. Role of serum amyloid A, granulocyte-macrophage colony stimulating factor, and bone marrow granulocyte-monocyte precursor expansion in segmented filamentous bacterium-mediated protection from Entamoeba histolytica. Infect. Immun. 84(10), 2824-2832 (2016).