420104

JAK3 Inhibitor II

Name: JAK3 Inhibitor II
Brand: MM

The JAK3 Inhibitor II, also referenced under CAS 211555-04-3, controls the biological activity of JAK3. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

Synonym(s):

JAK3 Inhibitor II, 4-[(3ʹ-Bromo-4ʹ-hydroxyphenyl)amino]-6,7-dimethoxyquinazoline, WHI-P154

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₄BrN₃O₃

CAS Number:

211555-04-3

Molecular Weight:

376.20

MDL number:

MFCD02179366

UNSPSC Code:

12352200

NACRES:

NA.77

Product Name

JAK3 Inhibitor II, The JAK3 Inhibitor II, also referenced under CAS 211555-04-3, controls the biological activity of JAK3. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

SMILES string

Brc1c(ccc(c1)Nc2ncnc3c2cc(c(c3)OC)OC)O

InChI

1S/C16H14BrN3O3/c1-22-14-6-10-12(7-15(14)23-2)18-8-19-16(10)20-9-3-4-13(21)11(17)5-9/h3-8,21H,1-2H3,(H,18,19,20)

InChI key

CBIAKDAYHRWZCU-UHFFFAOYSA-N

assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze
protect from light

color

pale yellow

solubility

DMSO: 100 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Bioactive Small Molecule Inhibitors

Biochem/physiol Actions

Cell permeable: yes

Primary Target
JAK-3

Product competes with ATP.

Reversible: yes

Target IC₅₀: 5.6 µM against JAK3

Disclaimer

Toxicity: Standard Handling (A)

General description

A potent, cell-permeable, reversible, ATP-competitive, and specific inhibitor of JAK3 (IC₅₀ = 5.6 µM). Has no effect on either JAK1 or JAK2. Has also been shown to prevent the ionizing radiation-induced activation of c-Jun in DT-40 cells. Also acts as a potent inhibitor of glioblastoma cell adhesion and migration.

Other Notes

Ghosh, S., et al. 2001. Acta Crystallogr. C.57, 76.
Sudbeck, E.A., et al. 1999. Clin. Cancer Res. 5, 1569.
Goodman, P.A., et al. 1998. J. Biol. Chem. 273, 17742.
Narla, R.K., et al. 1998. Clin Cancer Res.4, 2463.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

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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Inhibition of human glioblastoma cell adhesion and invasion by 4-(4'-hydroxylphenyl)-amino-6,7-dimethoxyquinazoline (WHI-P131) and 4-(3'-bromo-4'-hydroxylphenyl)-amino-6,7-dimethoxyquinazoline (WHI-P154).

R K Narla et al.

Clinical cancer research : an official journal of the American Association for Cancer Research, 4(10), 2463-2471 (1998-10-31)

Glioblastoma multiforme is a highly invasive primary brain tumor with a disappointingly high local recurrence rate and mortality despite intensive multimodality treatment programs. Therefore, new agents that are capable of inhibiting the infiltration of normal brain parenchyma by glioblastoma cells

4-[3-Bromo-4-hydroxyphenyl)amino]-6,7-dimethoxyquinazolin-1-ium chloride methanol solvate and 4-[(3-hydroxyphenyl)amino]-6,7-dimethoxy-1-quinazolinium chloride.

S Ghosh et al.

Acta crystallographica. Section C, Crystal structure communications, 57(Pt 1), 76-78 (2001-02-15)

The title compounds, C16H15BrN3(O3)(+).Cl(-).CH4O (WHI-P154) and C16H16N3(O3)(+).Cl(-) (WHI-P180), are potent inhibitors [WHI-P154 with IC50 = 5.6 microM and WHI-P180 with IC50 = 4.0 microM for epidermal growth factor receptor (EGFR) kinase inhibition] of the EGFR tyrosine kinase as well as

Structure-based design of specific inhibitors of Janus kinase 3 as apoptosis-inducing antileukemic agents.

E A Sudbeck et al.

Clinical cancer research : an official journal of the American Association for Cancer Research, 5(6), 1569-1582 (1999-07-02)

A novel homology model of the kinase domain of Janus kinase (JAK) 3 was used for the structure-based design of dimethoxyquinazoline compounds with potent and specific inhibitory activity against JAK3. The active site of JAK3 in this homology model measures

Role of tyrosine kinases in induction of the c-jun proto-oncogene in irradiated B-lineage lymphoid cells.

P A Goodman et al.

The Journal of biological chemistry, 273(28), 17742-17748 (1998-07-04)

Exposure of B-lineage lymphoid cells to ionizing radiation induces an elevation of c-jun proto-oncogene mRNA levels. This signal is abrogated by protein-tyrosine kinase (PTK) inhibitors, indicating that activation of an as yet unidentified PTK is mandatory for radiation-induced c-jun expression.