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Tbb

CAS No.:
17374-26-4
Catalog Number:
AG001Z5Q
Molecular Formula:
C6HBr4N3
Molecular Weight:
434.7082
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥98%
1 week
United States
$98
- +
10mg
≥98%
1 week
United States
$136
- +
25mg
≥98%
1 week
United States
$203
- +
50mg
≥98%
1 week
United States
$328
- +
Product Description
Catalog Number:
AG001Z5Q
Chemical Name:
Tbb
CAS Number:
17374-26-4
Molecular Formula:
C6HBr4N3
Molecular Weight:
434.7082
MDL Number:
MFCD06411399
IUPAC Name:
4,5,6,7-tetrabromo-2H-benzotriazole
InChI:
InChI=1S/C6HBr4N3/c7-1-2(8)4(10)6-5(3(1)9)11-13-12-6/h(H,11,12,13)
InChI Key:
OMZYUVOATZSGJY-UHFFFAOYSA-N
SMILES:
Brc1c(Br)c(Br)c2c(c1Br)[nH]nn2
NSC Number:
231634
Properties
Complexity:
184  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
434.686g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
434.711g/mol
Monoisotopic Mass:
430.69g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
41.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.8  
Literature
Title Journal
Raf-1/CK2 and RhoA/ROCK signaling promote TNF-α-mediated endothelial apoptosis via regulating vimentin cytoskeleton. Toxicology 20170815
CK2 activity is required for the interaction of FGF14 with voltage-gated sodium channels and neuronal excitability. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20160601
BET protein Brd4 activates transcription in neurons and BET inhibitor Jq1 blocks memory in mice. Nature neuroscience 20151001
Synthesis and physico-chemical properties in aqueous medium of all possible isomeric bromo analogues of benzo-1H-triazole, potential inhibitors of protein kinases. The journal of physical chemistry. B 20120621
Protein kinase CK2 mediates peroxynitrite-induced heme oxygenase-1 expression in articular chondrocytes. International journal of molecular medicine 20120601
Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors. Bioorganic & medicinal chemistry 20120401
Protein kinase CK2 triggers cytosolic zinc signaling pathways by phosphorylation of zinc channel ZIP7. Science signaling 20120207
A pharmacologically-based array to identify targets of cyclosporine A-induced toxicity in cultured renal proximal tubule cells. Toxicology and applied pharmacology 20120115
Time schedule-dependent effect of the CK2 inhibitor TBB on PC-3 human prostate cancer cell viability. Oncology reports 20120101
Influence of five potential anticancer drugs on wnt pathway and cell survival in human biliary tract cancer cells. International journal of biological sciences 20120101
Phosphorylation of CRN2 by CK2 regulates F-actin and Arp2/3 interaction and inhibits cell migration. Scientific reports 20120101
Inhibition of casein kinase 2 modulates XBP1-GRP78 arm of unfolded protein responses in cultured glial cells. PloS one 20120101
GPCRs regulate the assembly of a multienzyme complex for purine biosynthesis. Nature chemical biology 20111201
Multisite-directed inhibitors of protein kinase CK2: new challenges. Molecular and cellular biochemistry 20111001
Design and synthesis of CK2 inhibitors. Molecular and cellular biochemistry 20111001
Down-regulation of CK2 activity results in a decrease in the level of cdc25C phosphatase in different prostate cancer cell lines. Molecular and cellular biochemistry 20111001
The kinase DYRKIA regulates pre-mRNA splicing in spermatogonia and proliferation of spermatogonia and Sertoli cells by phosphorylating a spliceosomal component, SAP155, in postnatal murine testes. Molecular and cellular biochemistry 20110901
The protein kinase CK2 inhibitor TBB mediates up-regulation of MEK3/6 and p38δ activities, down-regulation of ERK1/2 activity and induction of G1/S arrest in normal human epidermal autocrine proliferating keratinocytes. Journal of dermatological science 20110801
The cytosolic protein kinase CK2 phosphorylates cardiac calsequestrin in intact cells. Molecular and cellular biochemistry 20110701
CK2 phosphorylates AP-2α and increases its transcriptional activity. BMB reports 20110701
Protein kinase CK2 increases glutamatergic input in the hypothalamus and sympathetic vasomotor tone in hypertension. The Journal of neuroscience : the official journal of the Society for Neuroscience 20110601
Brain-derived neurotrophic factor enhances Bcl-xL expression through protein kinase casein kinase 2-activated and nuclear factor kappa B-mediated pathway in rat hippocampus. Brain pathology (Zurich, Switzerland) 20110301
Treatment of cultured human astrocytes and vascular endothelial cells with protein kinase CK2 inhibitors induces early changes in cell shape and cytoskeleton. Molecular and cellular biochemistry 20110301
CK2 inhibition induces apoptosis via the ER stress response. Cellular signalling 20110101
A specific inhibitor of protein kinase CK2 delays gamma-H2Ax foci removal and reduces clonogenic survival of irradiated mammalian cells. Radiation oncology (London, England) 20110101
CK2 is acting upstream of MEK3/6 as a part of the signal control of ERK1/2 and p38 MAPK during keratinocytes autocrine differentiation. Zeitschrift fur Naturforschung. C, Journal of biosciences 20110101
IL-6 stabilizes Twist and enhances tumor cell motility in head and neck cancer cells through activation of casein kinase 2. PloS one 20110101
Downregulation of protein kinase CK2 activity facilitates tumor necrosis factor-α-mediated chondrocyte death through apoptosis and autophagy. PloS one 20110101
Bromophenols in marine algae and their bioactivities. Marine drugs 20110101
Apigenin inhibits proliferation and induces apoptosis in human multiple myeloma cells through targeting the trinity of CK2, Cdc37 and Hsp90. Molecular cancer 20110101
CK2 phosphorylation of Schistosoma mansoni HMGB1 protein regulates its cellular traffic and secretion but not its DNA transactions. PloS one 20110101
Label-free integrative pharmacology on-target of drugs at the β(2)-adrenergic receptor. Scientific reports 20110101
Facilitation of long-term potentiation by muscarinic M(1) receptors is mediated by inhibition of SK channels. Neuron 20101209
Reconstitution of PTEN activity by CK2 inhibitors and interference with the PI3-K/Akt cascade counteract the antiapoptotic effect of human stromal cells in chronic lymphocytic leukemia. Blood 20101007
Phosphorylation of the von Hippel-Lindau protein (VHL) by protein kinase CK2 reduces its protein stability and affects p53 and HIF-1alpha mediated transcription. The international journal of biochemistry & cell biology 20101001
The inhibitory effect of acrylamide on NCAM expression in human neuroblastoma cells: involvement of CK2/Ikaros signaling pathway. Toxicology in vitro : an international journal published in association with BIBRA 20101001
Relative role of halogen bonds and hydrophobic interactions in inhibition of human protein kinase CK2α by tetrabromobenzotriazole and some C5-substituted analogues. The journal of physical chemistry. B 20100819
A medicinal chemist's guide to molecular interactions. Journal of medicinal chemistry 20100722
Genome-wide screen in Saccharomyces cerevisiae identifies vacuolar protein sorting, autophagy, biosynthetic, and tRNA methylation genes involved in life span regulation. PLoS genetics 20100701
Casein kinase 2 inhibition differentially modulates apoptotic effect of trichostatin A against epithelial ovarian carcinoma cell lines. Molecular and cellular biochemistry 20100501
Dynamic regulation of a metabolic multi-enzyme complex by protein kinase CK2. The Journal of biological chemistry 20100409
A FRET-based microplate assay for human protein kinase CK2, a target in neoplastic disease. Journal of enzyme inhibition and medicinal chemistry 20100401
Regulation of PTEN by CK2 and Notch1 in primary T-cell acute lymphoblastic leukemia: rationale for combined use of CK2- and gamma-secretase inhibitors. Haematologica 20100401
p53 is dispensable for the induction of apoptosis after inhibition of protein kinase CK2. The Prostate 20100201
Halogenated imidazole derivatives block RNA polymerase II elongation along mitogen inducible genes. BMC molecular biology 20100101
A CE-based assay for human protein kinase CK2 activity measurement and inhibitor screening. Electrophoresis 20100101
Conserved and distinct modes of CREB/ATF transcription factor regulation by PP2A/B56gamma and genotoxic stress. PloS one 20100101
Kinome profiling of myxoid liposarcoma reveals NF-kappaB-pathway kinase activity and casein kinase II inhibition as a potential treatment option. Molecular cancer 20100101
The 14-3-3ζ protein binds to the cell adhesion molecule L1, promotes L1 phosphorylation by CKII and influences L1-dependent neurite outgrowth. PloS one 20100101
Protein kinase C and rho activated coiled coil protein kinase 2 (ROCK2) modulate Alzheimer's APP metabolism and phosphorylation of the Vps10-domain protein, SorL1. Molecular neurodegeneration 20100101
Efficacy and mechanism of anti-tumor action of new potential CK2 inhibitors toward glioblastoma cells. International journal of oncology 20091101
Selectivity analysis of protein kinase CK2 inhibitors DMAT, TBB and resorufin in cisplatin-induced stress responses. International journal of oncology 20091101
Protein kinase CK2 regulates cytoskeletal reorganization during ionizing radiation-induced senescence of human mesenchymal stem cells. Cancer research 20091015
PACS-1 mediates phosphorylation-dependent ciliary trafficking of the cyclic-nucleotide-gated channel in olfactory sensory neurons. The Journal of neuroscience : the official journal of the Society for Neuroscience 20090826
Inhibition of protein kinase CK2 induces E2F1 nuclear export, formation of p21/E2F1 complexes and suppression of DNA synthesis in normal human epidermal keratinocytes. Journal of dermatological science 20090801
Involvement of reactive oxygen species in apoptosis induced by pharmacological inhibition of protein kinase CK2. Annals of the New York Academy of Sciences 20090801
Structural insight into human CK2alpha in complex with the potent inhibitor ellagic acid. Bioorganic & medicinal chemistry letters 20090601
DMAT, an inhibitor of protein kinase CK2 induces reactive oxygen species and DNA double strand breaks. Oncology reports 20090601
Synthesis of new analogs of benzotriazole, benzimidazole and phthalimide--potential inhibitors of human protein kinase CK2. Bioorganic & medicinal chemistry 20090215
Phosphorylation of the HuR ligand APRIL by casein kinase 2 regulates CD83 expression. European journal of immunology 20090101
Identification of hematein as a novel inhibitor of protein kinase CK2 from a natural product library. BMC cancer 20090101
The selectivity of inhibitors of protein kinase CK2: an update. The Biochemical journal 20081101
Protein kinase CK2 catalyzes tyrosine phosphorylation in mammalian cells. Cellular signalling 20081101
New inhibitors of protein kinase CK2, analogues of benzimidazole and benzotriazole. Molecular and cellular biochemistry 20080901
Evaluating CK2 activity with the antibody specific for the CK2-phosphorylated form of a kinase-targeting cochaperone Cdc37. Molecular and cellular biochemistry 20080901
Impact of protein kinase CK2 on inhibitor of apoptosis proteins in prostate cancer cells. Molecular and cellular biochemistry 20080901
Role of heme oxygenase-2 in pial arteriolar response to acetylcholine in mice with and without transfusion of cell-free hemoglobin polymers. American journal of physiology. Regulatory, integrative and comparative physiology 20080801
Hemoglobin neurotoxicity is attenuated by inhibitors of the protein kinase CK2 independent of heme oxygenase activity. Current neurovascular research 20080801
Protein kinase CK2 modulates synaptic plasticity by modification of synaptic NMDA receptors in the hippocampus. The Journal of physiology 20080701
An unbiased evaluation of CK2 inhibitors by chemoproteomics: characterization of inhibitor effects on CK2 and identification of novel inhibitor targets. Molecular & cellular proteomics : MCP 20080601
Regulation of the epithelial Na+ channel by the protein kinase CK2. The Journal of biological chemistry 20080509
Inhibition of casein kinase 2 enhances the death ligand- and natural kiler cell-induced hepatocellular carcinoma cell death. Clinical and experimental immunology 20080501
A role for CK2 upon interkinetic nuclear migration in the cell cycle of retinal progenitor cells. Developmental neurobiology 20080401
CK2beta gene silencing increases cell susceptibility to influenza A virus infection resulting in accelerated virus entry and higher viral protein content. Journal of molecular signaling 20080101
Ecto-phosphorylation of CD98 regulates cell-cell interactions. PloS one 20080101
A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases. Proceedings of the National Academy of Sciences of the United States of America 20071218
Inhibition of HCV replicon cell growth by 2-arylbenzofuran derivatives isolated from Mori Cortex Radicis. Planta medica 20071101
The reverse in-gel kinase assay to profile physiological kinase substrates. Nature methods 20071101
Organization and regulation of small conductance Ca2+-activated K+ channel multiprotein complexes. The Journal of neuroscience : the official journal of the Society for Neuroscience 20070227
Protein kinase CK2alpha as an unfavorable prognostic marker and novel therapeutic target in acute myeloid leukemia. Clinical cancer research : an official journal of the American Association for Cancer Research 20070201
Tetrabromocinnamic acid (TBCA) and related compounds represent a new class of specific protein kinase CK2 inhibitors. Chembiochem : a European journal of chemical biology 20070102
CK2 phosphorylation of SAG at Thr10 regulates SAG stability, but not its E3 ligase activity. Molecular and cellular biochemistry 20070101
Differential regulation of mouse equilibrative nucleoside transporter 1 (mENT1) splice variants by protein kinase CK2. Molecular membrane biology 20070101
A CK2-dependent mechanism for degradation of the PML tumor suppressor. Cell 20060728
Expression of protein kinase CK2 in astroglial cells of normal and neovascularized retina. The American journal of pathology 20060501
Intracellular hydrogen peroxide production is an upstream event in apoptosis induced by down-regulation of casein kinase 2 in prostate cancer cells. Molecular cancer research : MCR 20060501
Role of protein kinase CK2 in the regulation of tumor necrosis factor-related apoptosis inducing ligand-induced apoptosis in prostate cancer cells. Cancer research 20060215
Adaptor heat shock protein complex formation regulates trafficking of the asialoglycoprotein receptor. American journal of physiology. Gastrointestinal and liver physiology 20060201
Transcriptional analysis of calcium-dependent and calcium-independent signalling pathways induced by oligogalacturonides. Journal of experimental botany 20060101
Tetrabromobenzotriazole (TBBt) and tetrabromobenzimidazole (TBBz) as selective inhibitors of protein kinase CK2: evaluation of their effects on cells and different molecular forms of human CK2. Biochimica et biophysica acta 20051230
CDK phosphorylation inhibits the DNA-binding and ATP-hydrolysis activities of the Drosophila origin recognition complex. The Journal of biological chemistry 20051202
A protein kinase CK2 site flanking the nuclear targeting signal enhances nuclear transport of human cytomegalovirus ppUL44. Traffic (Copenhagen, Denmark) 20051101
Development and exploitation of CK2 inhibitors. Molecular and cellular biochemistry 20050601
Phosphorylation of the acidic domain of Mdm2 by protein kinase CK2. Molecular and cellular biochemistry 20050601
Spinal CK2 regulates nociceptive signaling in models of inflammatory pain. Pain 20050501
Control of hepatitis C: a medicinal chemistry perspective. Journal of medicinal chemistry 20050113
Synthesis and biological activity of 1H-benzotriazole and 1H-benzimidazole analogues--inhibitors of the NTpase/helicase of HCV and of some related Flaviviridae. Antiviral chemistry & chemotherapy 20050101
Optimization of protein kinase CK2 inhibitors derived from 4,5,6,7-tetrabromobenzimidazole. Journal of medicinal chemistry 20041202
Inhibitors of the NTPase/helicases of hepatitis C and related Flaviviridae viruses. Acta poloniae pharmaceutica 20041201
Flow-dependent regulation of endothelial Toll-like receptor 2 expression through inhibition of SP1 activity. Circulation research 20041001
2-Dimethylamino-4,5,6,7-tetrabromo-1H-benzimidazole: a novel powerful and selective inhibitor of protein kinase CK2. Biochemical and biophysical research communications 20040903
Expression of the Stp1 LMW-PTP and inhibition of protein CK2 display a cooperative effect on immunophilin Fpr3 tyrosine phosphorylation and Saccharomyces cerevisiae growth. Cellular and molecular life sciences : CMLS 20040501
Protein kinase CK2 phosphorylates the cell cycle regulatory protein Geminin. Biochemical and biophysical research communications 20040319
TBBz but not TBBt discriminates between two molecular forms of CK2 in vivo and its implications. Biochemical and biophysical research communications 20031219
Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid (IQA). The Biochemical journal 20030915
Alternative binding modes of an inhibitor to two different kinases. European journal of biochemistry 20030801
Selectivity of 4,5,6,7-tetrabromobenzimidazole as an ATP-competitive potent inhibitor of protein kinase CK2 from various sources. Biochemical and biophysical research communications 20030620
Halogenated benzimidazoles and benzotriazoles as inhibitors of the NTPase/helicase activities of hepatitis C and related viruses. European journal of biochemistry 20030401
The role of calcium in oligogalacturonide-activated signalling in soybean cells. Planta 20020801
Identification of protein kinase CK2 as a potent kinase of Epstein-Barr virus latent membrane protein 1. Biochemical and biophysical research communications 20020614
Protein kinase CK2 inhibitor 4,5,6,7-tetrabromobenzotriazole (TBB) induces apoptosis and caspase-dependent degradation of haematopoietic lineage cell-specific protein 1 (HS1) in Jurkat cells. The Biochemical journal 20020515
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells. The Journal of biological chemistry 20020419
Toward the rational design of protein kinase casein kinase-2 inhibitors. Pharmacology & therapeutics 20020101
Structural features underlying selective inhibition of protein kinase CK2 by ATP site-directed tetrabromo-2-benzotriazole. Protein science : a publication of the Protein Society 20011101
Selectivity of 4,5,6,7-tetrabromobenzotriazole, an ATP site-directed inhibitor of protein kinase CK2 ('casein kinase-2'). FEBS letters 20010504
Properties