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SML2044

Sigma-Aldrich

DMAT

≥98% (HPLC)

Synonym(s):

CK2 Inhibitor II, 2-Dimethylamino-4,5,6,7-tetrabromo-1H-benzimidazole, 4,5,6,7-Tetrabromo-N,N-dimethyl-1H-benzimidazol-2-amine, 4,5,6,7-Tetrabromo-N,N-dimethyl-1H-benzo[d]imidazol-2-amine, DMAT

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About This Item

Empirical Formula (Hill Notation):
C9H7Br4N3
CAS Number:
749234-11-5
Molecular Weight:
476.79
MDL number:
MFCD08705322
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

shipped in

wet ice

storage temp.

−20°C

SMILES string

CN(C)c1nc2c(Br)c(Br)c(Br)c(Br)c2[nH]1

InChI

1S/C9H7Br4N3/c1-16(2)9-14-7-5(12)3(10)4(11)6(13)8(7)15-9/h1-2H3,(H,14,15)

InChI key

SLPJGDQJLTYWCI-UHFFFAOYSA-N

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Application

DMAT has been used as a casein kinase 2 (CK2) inhibitor:
  • to study its effects on parasite multiplication in a [3H]-hypoxanthine incorporation assay
  • to study its effects on the intracellular response in prostate cancer cells
  • to study its effects on cell division cycle 25C (cdc25C) phosphatase levels in prostate cancer cells

Biochem/physiol Actions

Casein kinase II inhibitor II (Ck2 Inhibitor II) is a high affinity ATP-competitive inhibitor of casein kinase II. Ck2 Inhibitor II inhibits CK2 in rat liver with 1,300-fold greater selectivity for CK2 than for CK1 (IC50 = 140 nM and >200 μM respectively). Ki = 40 nM; In Jurkat human T-cell leukemia cells, Ck2 Inhibitor II does not display side effects on mitochondria polarization at concentrations up to 10 μM; Ck2 Inhibitor II is useful for in vivo studies due to cell permeability and high efficacy in cultured cells and has implications in research and treatment of neoplasia and infective diseases, in which CK2 plays a role and is highly active constitutively.
DMAT is an ATP-competitive (Ki = 40 nM) casein kinase 2 (CK2) inhibitor (IC50 = 140 nM; rat liver CK2, [ATP] = 20 nM) with greatly improved potency and selectivity than its structure analog TBB. With the exception of DYRK1a (IC50 = 120 nM), DMAT is reported to exhibit no CK1 inhibitiory potency up to 200 μM (50% inhibition by 29 μM TBB) and little or no activity against a panel of 32 other protein kinases, nor PI3K α and γ. When tested in Jurkat cultures, DMAT is shown to be a superior apoptosis inducer than TBB (DC50 = 2.7 μM/DMAT vs. 17 μM/TBB).

Caution

Air sensitive

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Mario A Pagano et al.
Biochemical and biophysical research communications, 321(4), 1040-1044 (2004-09-11)
Protein kinase CK2 is a highly pleiotropic enzyme whose high constitutive activity is suspected to be instrumental to the enhancement of the tumour phenotype and to the propagation of infectious diseases. Here we describe a novel compound, 2-dimethylamino-4,5,6,7-tetrabromo-1H-benzimidazole (DMAT), which
Mario A Pagano et al.
Journal of medicinal chemistry, 47(25), 6239-6247 (2004-11-30)
Casein kinase 2 (CK2) is a ubiquitous, essential, and highly pleiotropic protein kinase whose abnormally high constitutive activity is suspected to underlie its pathogenic potential in neoplasia and infective diseases. Thus, CK2 inhibitors designed to dissect the signaling pathways affected
Carolin C Schneider et al.
Oncology reports, 21(6), 1593-1597 (2009-05-09)
Elevated levels of protein kinase CK2 were found in tumour cells compared to normal cells. Thus, inhibition of CK2 kinase activity seems to be an attractive method to stop growth of cancer cells. Two drugs, namely tetrabromobenzotriazole, TBB, and 2-dimethylamino-4,5,6,7-tetrabromo-1H-benzimidazole
Carolin C Schneider et al.
Molecular and cellular biochemistry, 356(1-2), 177-184 (2011-07-14)
Protein kinase CK2 is implicated in the regulation of the cell cycle. In addition to a variety of functions, CK2 has anti-apoptotic properties. So far the role of CK2 linking both pathways in the cell is not clear. Some years
Konrad Kubiński et al.
Molecular and cellular biochemistry, 426(1-2), 195-203 (2016-12-03)
Benzimidazole derivatives of 5,6-dichlorobenzimidazole 1-β-D-ribofuranoside (DRB) comprise the important class of protein kinase CK2 inhibitors. Depending on the structure, benzimidazoles inhibit CK2 with different selectivity and potency. Besides CK2, the compounds can inhibit, with similar activity, other classical eukaryotic protein
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