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5.30654

Sigma-Aldrich

c-Rel Inhibitor, IT-603

Synonym(s):

c-Rel Inhibitor, IT-603, (5 Z)-5-((5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene)-2-sulfanylideneimidazolidin-4-one, (5 Z)-5-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-2-thioxo-4-imidazolidinone, IT603, (5Z)-5-((5-Bromo-2-hydroxy-3-methoxyphenyl)methylidene)-2-sulfanylideneimidazolidin-4-one, (5Z)-5-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-2-thioxo-4-imidazolidinone, IT603

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About This Item

Empirical Formula (Hill Notation):
C11H9BrN2O3S
CAS Number:
292168-90-2
Molecular Weight:
329.17
MDL number:
MFCD02109025
UNSPSC Code:
51111800
PubChem Substance ID:
840180
NACRES:
NA.77

Assay

≥97% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

dark yellow

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

SMILES string

COC1=CC(=CC(=C1O)C=C2C(=O)NC(=S)N2)Br

InChI

1S/C11H9BrN2O3S/c1-17-8-4-6(12)2-5(9(8)15)3-7-10(16)14-11(18)13-7/h2-4,15H,1H3,(H2,13,14,16,18)

InChI key

PYLYAEDUIKQBOT-UHFFFAOYSA-N

General description

A cell-permeable benzylidene-thioxo-imidazolidinone compund that directly and reversibly binds to c-Rel to change its conformation and blocks its DNA binding and transcriptional activity (IC50 = 3 µM in EMSA). Shows good selectivity over Oct1 and AP1. Reduces IL-2 expression in activated T cells without affecting their viability. Induces growth arrest in diffuse large B-cell lymphoma (DLBCL) cell line Ly3 (IC50 = 18 uM). Shown to reduce alloactivation in T cells and diminish graft-versus-host disease (GVHD), but does not impair TCR-mediated killing. Improves the survival rate of lethally irradiated BABL/c mice transplanted with T cell depleted bone marrow cells from C57BL/6 mice (~24 mg/kg, i.p, daily).

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
c-Rel
Reversible: yes

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Use only fresh DMSO for reconstitution.

Other Notes

Shono, Y., et al. 2014. Cancer Discovery4, 578.

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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Global Trade Item Number

SKUGTIN
5.30654.000104055977260410

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