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407602

Sigma-Aldrich

Interleukin-1 Receptor-Associated-Kinase-1/4 Inhibitor

InSolution, ≥98%

Synonym(s):

InSolution Interleukin-1 Receptor-Associated-Kinase-1/4 Inhibitor, N-(1-(2-morpholinoethyl)-1H-benzo[d]imidazol-2-yl)-3-nitrobenzamide, N-(2-Morpholinylethyl)-2-(3-nitrobenzoylamido)-benzimidazole

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About This Item

Empirical Formula (Hill Notation):
C20H21N5O4
CAS Number:
509093-47-4
Molecular Weight:
395.41
MDL number:
MFCD09752602
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
avoid repeated freeze/thaw cycles
desiccated (hygroscopic)
protect from light

shipped in

dry ice

storage temp.

−70°C

InChI

1S/C20H21N5O4/c26-19(15-4-3-5-16(14-15)25(27)28)22-20-21-17-6-1-2-7-18(17)24(20)9-8-23-10-12-29-13-11-23/h1-7,14H,8-13H2,(H,21,22,26)

InChI key

QTCFYQHZJIIHBS-UHFFFAOYSA-N

General description

A cell-permeable benzimidazole compound that acts as a potent and selective inhibitor of interleukin-1 receptor-associated kinases (IC50 = 300 nM and 200 nM for IRAK-1 and -4). Shown to exhibit little activity against a panel of 27 other kinases (IC50 >10 µM), including lck and src. The solid form of this compound (Cat. No. 407601) is also available.

Biochem/physiol Actions

Primary Target
IRAK-1/4
Reversible: yes
Target IC50: 300 nM and 200 nM for IRAK-1 and -4

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Physical form

A 25 mM (5 mg/506 µL) solution of Interleukin-1 Receptor-Associated-Kinase-1/4 Inhibitor (Cat. No. 407601) in DMSO.

Reconstitution

Following initial thaw, aliquot and freeze (-70°C). Aliquots are stable for up to 6 months at -70°C.

Other Notes

Srivastava, R., et al. 2012. Cancer Res.72, In press.
Bhattacharyya, S., et al. 2007. Am. J. Physiol. Gastrointest. Liver Physiol.293, G429.
Powers, J.P., et al. 2006. Bioorg. Med. Chem. Lett.16, 2842.

Legal Information

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

188.6 °F - closed cup - (refers to pure substance)

Flash Point(C)

87 °C - closed cup - (refers to pure substance)

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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Humayara Khan et al.
3 Biotech, 13(1), 14-14 (2022-12-22)
Combination of docetaxel, cisplatin and 5-FU, known as TPF, is an FDA-approved treatment for head and neck squamous cell carcinoma (HNSCC). Acquired chemo-resistance to TPF, a primary reason for non-responsiveness to the treatment and relapse of tumor is a major
Ratika Srivastava et al.
Cancer research, 72(23), 6209-6216 (2012-10-09)
Toll-like receptors (TLR) are expressed by a variety of cancers, including melanoma, but their functional contributions in cancer cells are uncertain. To approach this question, we evaluated the effects of stimulating or inhibiting the TLR/IL-1 receptor-associated kinases IRAK-1 and IRAK-4
Jay P Powers et al.
Bioorganic & medicinal chemistry letters, 16(11), 2842-2845 (2006-03-28)
High-throughput screening of a small-molecule compound library resulted in the identification of a novel series of N-acyl 2-aminobenzimidazoles that are potent inhibitors of interleukin-1 receptor-associated kinase-4.
Sumit Bhattacharyya et al.
American journal of physiology. Gastrointestinal and liver physiology, 293(2), G429-G437 (2007-06-02)
Lipopolysaccharide (LPS) is recognized as an inducer of the inflammatory response associated with gram-negative sepsis and systemic inflammatory response syndrome. LPS induction proceeds through Toll-like receptor (TLR) in immune cells and intestinal epithelial cells (IEC). This report presents the first

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