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420148

Sigma-Aldrich

JAK3/GSK-3β/PKCα Inhibitor

The JAK3/GSK-3β/PKCα Inhibitor, also referenced under CAS 1260181-14-3, controls the biological activity of JAK3/GSK-3β/PKCα. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

Synonym(s):

JAK3/GSK-3β/PKCα Inhibitor, 3-(5-(4-(2-Hydroxy-2-methyl-propionyl)-piperazin-1-yl)-2-trifluoromethyl-phenyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione, JAK3 Inhibitor XII, NIBR3049, JAK3 Inhibitor XII, NIBR3049, 3-(5-(4-(2-Hydroxy-2-methyl-propionyl)-piperazin-1-yl)-2-trifluoromethyl-phenyl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione

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About This Item

Empirical Formula (Hill Notation):
C27H25F3N4O4
CAS Number:
1260181-14-3
Molecular Weight:
526.51
MDL number:
MFCD19380092
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

yellow

solubility

DMSO: soluble

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C1NC(C(C2=CNC3=C2C=CC=C3)=C1C4=CC(N5CCN(C(C(C)(C)O)=O)CC5)=CC=C4C(F)(F)F)=O

InChI

1S/C27H25F3N4O4/c1-26(2,38)25(37)34-11-9-33(10-12-34)15-7-8-19(27(28,29)30)17(13-15)21-22(24(36)32-23(21)35)18-14-31-20-6-4-3-5-16(18)20/h3-8,13-14,31,38H,9-12H2,1-2H3,(H,32,35,36)

InChI key

CLGRAWDGLMENOD-UHFFFAOYSA-N

General description

A cell-permeable phenyl-indolyl maleimide compound that acts as a potent, ATP-binding site targeting and reversible inhibitor of GSK-3β, JAK3, PKCα and PKCθ (IC50 = 3, 8, 13 and 68 nM, respectively) with excellent selectivity over 40-kinases, including JAK1, JAK2 and Tyk2 (IC50 = 1.017, 2.55 and 8.055 µM, respectively). Shown to efficiently block interleukin stimulated STAT5 phosphorylation and T cell costimulation (IC50 = 0.525, 1.294 and 0.689 µM in IL15-MO7, IL2-CTLL and TCR/CD28-Jurkat cells, respectively).

Packaging

Packaged under inert gas

Other Notes

Haan, C., et al. 2011. Chem. Biol.18, 314.
Thoma, G., et al. 2011. J. Med. Chem.54, 284.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gebhard Thoma et al.
Journal of medicinal chemistry, 54(1), 284-288 (2010-12-16)
We describe a synthetic approach toward the rapid modification of phenyl-indolyl maleimides and the discovery of potent Jak3 inhibitor 1 with high selectivity within the Jak kinase family. We provide a rationale for this unprecedented selectivity based on the X-ray
Claude Haan et al.
Chemistry & biology, 18(3), 314-323 (2011-03-29)
Genetic deficiency of Jak3 leads to abrogation of signal transduction through the common gamma chain (γc) and thus to immunodeficiency suggesting that specific inhibition of Jak3 kinase may result in immunosuppression. Jak1 cooperates with Jak3 in signaling through γc-containing receptors.

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