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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)

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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Alexander Ulges et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(36), 10145-10150 (2016-08-25)
T helper 17 (TH17) cells represent a discrete TH cell subset instrumental in the immune response to extracellular bacteria and fungi. However, TH17 cells are considered to be detrimentally involved in autoimmune diseases like multiple sclerosis (MS). In contrast to
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
Qiang Chen et al.
Cell reports, 18(13), 3155-3166 (2017-03-30)
Preadipocytes initiate differentiation into adipocytes through a cascade of events. Mitotic clonal expansion, as one of the earliest events, is essential for adipogenesis. However, the underlying mechanisms that regulate mitotic clonal expansion remain elusive. SIRT6 is a member of the
Da Hye Jung et al.
Immunologic research, 62(1), 35-45 (2015-03-11)
Macrophage-associated nitric oxide (NO) production plays a crucial role in the pathogenesis of tissue damage. However, negative factors that regulate NO production remains poorly understood despite its significance of NO homeostasis. Here, we show that activating transcription factor 3 (ATF3)
Claudia Götz et al.
Biochimica et biophysica acta, 1820(7), 970-977 (2012-03-06)
Abnormally high activity of protein kinase CK2 is linked to various diseases including cancer. Therefore, the inhibition of CK2 is a promising therapeutic strategy to fight this disease. We screened a library of synthetic molecules concerning their capacity to inhibit
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