![4,5,6,7-TETRABROMO-1H-BENZO[D][1,2,3]TRIAZOLE structure, CAS 17374-26-4](/structures/150000/133177_1_17374_26_4.png)
CAS Number17374-26-4
Synonyms4,5,6,7-Tetrabromo-1H-benzotriazole; 4,5,6,7-Tetrabromobenzotriazole; 4,5,6,7-tetrabromo-2H-benzotriazole; 4,5,6,7-Tetrabromo-2-azabenzimidazole 4,5,6,7-Tetrabromobenzotriazole; 4,5,6,7-tetrabromo-2-azabenzimidazole; 4,5,6,7-Tetrabromo-2-azabenzimidazole,4,5,6,7-Tetrabromobenzotriazole; TBB; NSC 231634
Molecular FormulaC6HBr4N3
Molecular Weight434.71
Purity≥98 (HPLC)%
Density2.8±0.1 g/cm3
Boiling Point552.5±45.0 °C at 760 mmHg
Melting Point262-266ºC
Appearancesolid
EINECS0
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 17374-26-4 |
| Catalog No. | 2A-0133177 |
| Chinese Name | 4,5,6,7-四溴苯甲腈 |
| Synonyms | 4,5,6,7-Tetrabromo-1H-benzotriazole; 4,5,6,7-Tetrabromobenzotriazole; 4,5,6,7-tetrabromo-2H-benzotriazole; 4,5,6,7-Tetrabromo-2-azabenzimidazole 4,5,6,7-Tetrabromobenzotriazole; 4,5,6,7-tetrabromo-2-azabenzimidazole; 4,5,6,7-Tetrabromo-2-azabenzimidazole,4,5,6,7-Tetrabromobenzotriazole; TBB; NSC 231634 |
| Molecular Formula | C6HBr4N3 |
| Molecular Weight | 434.71 |
| Purity | ≥98 (HPLC) |
| Density | 2.8±0.1 g/cm3 |
| Boiling Point | 552.5±45.0 °C at 760 mmHg |
| Melting Point | 262-266ºC |
| Appearance | solid |
| Storage Condition | 0-10°C; avoid heating |
| Application | TBB is a cell-permeable, ATP-competitive CK2 inhibitor. The IC50 value for inhibiting CK2 in rat liver is 0.15 μM. |
| EINECS | 0 |
| HTC | 2933990090 |
| UN(IATA) | 0 |
| PubChem ID | 24724628 |
| MDL Number | MFCD06411399 |
| SMILES | Brc1c(Br)c(Br)c2[nH]nnc2c1Br |
| 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/133177_1_17374_26_4.pdf |
| Bioactivity | TBB is a cell-permeable and ATP-competitive CK2 inhibitor with an IC50 of 0.15 μM for rat liver CK2. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Casein Kinase Signaling Pathways >> Stem Cell/Wnt >> Casein Kinase Research Areas >> Cancer Target CK2:0.15 μM (IC50, Human CK2) PIM1:1.04 μM (IC50) PIM2:4.3 μM (IC50) PIM3:0.86 μM (IC50) HIPK2:5.3 μM (IC50) HIPK3:4.9 μM (IC50) DYRK1a:4.36 μM (IC50) DYRK2:0.99 μM (IC50) DYRK3:5.3 μM (IC50) PKD1:5.9 μM (IC50) CDK2:14 μM (IC50) In Vitro Investigation of the inhibitory power of TBB with a panel of 33 protein kinases shows highest potency for CK2 (casein kinase 2) (human CK2: IC50=1.6 μM at 100 μM ATP). TBB also inhibits three other kinases with less potency: CDK2 (IC50=15.6 μM), phosphorylase kinase (IC50=8.7 μM) and glycogen synthase kinase 3β (GSK3β) (IC50=11.2 μM). All other kinases tested have IC50 values 50-fold greater than that for CK2[1]. The viability of the androgen insensitive PC-3 cells may be diminished by TBB (60 μM TBB) acting either alone or combined with anticancer agents CPT or TRAIL when a proper time schedule of the administration is applied. The time schedule-dependent activity of TBB does not come from its effect on apoptosis in PC-3 cells[2]. TBB is an ATP/GTP competitive inhibitor of protein kinase casein kinase-2 (CK2), has been examined against a panel of 33 protein kinases, either Ser/Thr- or Tyr-specific. In the presence of 10 μM TBB (and 100 μM ATP) only CK2 is drastically inhibited (>85%) whereas three kinases (phosphorylase kinase, glycogen synthase kinase 3L and cyclin-dependent kinase 2/cyclin A) underwent moderate inhibition, with IC50 values one-two orders of magnitude higher than CK2 (IC50=0.9 μM). TBB also inhibits endogenous CK2 in cultured Jurkat cells[3]. In Vivo The extent of retinal neovascularization in a mouse OIR model is reduced by approximately 60% after treatment with TBB (6 days at 60 mg/kg per day)[4]. Cell Assay PC-3 or HeLa cells are cultured routinely in RPMI-1640 and DMEM media, respectively, which are supplemented with 10% FBS, Penicillin (100 U/mL) and Streptomycin (100 μg/mL) at 37°C in a humidified atmosphere of 5% CO2. Cells are seeded at 5×104 cells/well (PC-3) or 2×104 (HeLa) in 24-wells plates and cultured for 72 h. TBB (final concentration 60 μM), CPT (final concentration 5.8 nM), 2-deoxyglucose (2-DG; final concentration 0.5 mM) or TRAIL (final concentration 13.3 ng/mL) are added to the medium individually or in a combination and the cells are cultured for additional time, indicated on each figure. After treatment, the medium with the agent is removed and 500 μL of MTT mixture (0.5 mg/mL for PC-3 and 5.0 mg/mL for HeLa cells in medium without phenol red) is added to each well and incubated for an additional 1 h at 37°C. The formazan crystals are diluted in 250 μL of DMSO. The absorbance is measured at 570 nm[2]. Animal Admin Mice[4] The heterozygous C57BL/6J mice are used. Emodin and TBB are injected intraperitoneally in volumes of 50 μL or less per mouse at doses of 15 to 30 mg/kg body weight, twice daily, starting from day 11. Control mice are injected with PEG-Tween vehicle alone. References [1]. De Moliner E, et al. Alternative binding modes of an inhibitor to two different kinases. Eur J Biochem. 2003 Aug;270(15):3174-81. [2]. Orzechowska E, et al. Time schedule-dependent effect of the CK2 inhibitor TBB on PC-3 human prostate cancer cell viability. Oncol Rep. 2012 Jan;27(1):281-5. [3]. Sarno S, et al. Selectivity of 4,5,6,7-tetrabromobenzotriazole, an ATP site-directed inhibitor of protein kinase CK2 ('casein kinase-2'). FEBS Lett. 2001 May 4;496(1):44-8. [4]. Ljubimov AV, et al. Involvement of protein kinase CK2 in angiogenesis and retinal neovascularization. Invest Ophthalmol Vis Sci. 2004 Dec;45(12):4583-91. [5]. Pagano MA, et al. The selectivity of inhibitors of protein kinase CK2: an update. Biochem J. 2008 Nov 1;415(3):353-65. [6]. Chen Z, et al. CK2α promotes advanced glycation end products-induced expressions of fibronectin and intercellular adhesion molecule-1 via activating MRTF-A in glomerular mesangial cells. Biochem Pharmacol. 2017 Dec 6;148:41-51. Chemical & Physical Properties Density 2.8±0.1 g/cm3 Boiling Point 552.5±45.0 °C at 760 mmHg Melting Point 262-266ºC Molecular Formula C6HBr4N3 Molecular Weight 434.708 Flash Point 288.0±28.7 °C Exact Mass 430.690369 PSA 41.57000 LogP 3.96 Vapour Pressure 0.0±1.5 mmHg at 25°C Index of Refraction 1.801 InChIKey OMZYUVOATZSGJY-UHFFFAOYSA-N SMILES Brc1c(Br)c(Br)c2n[nH]nc2c1Br |
| Use of | TBB is a cell-permeable and ATP-competitive CK2 inhibitor with an IC50 of 0.15 μM for rat liver CK2. Properties Articles17 Name 4,5,6,7-Tetrabromo-1H-benzotriazole Synonym More Synonyms TBB Biological Activity Description TBB is a cell-permeable and ATP-competitive CK2 inhibitor with an IC50 of 0.15 μM for rat liver CK2. Related Catalog Signaling Pathways >> Cell Cycle/DNA Damage >> Casein Kinase Signaling Pathways >> Stem Cell/Wnt >> Casein Kinase Research Areas >> Cancer CK2:0.15 μM (IC50, Human CK2) PIM1:1.04 μM (IC50) PIM2:4.3 μM (IC50) PIM3:0.86 μM (IC50) HIPK2:5.3 μM (IC50) HIPK3:4.9 μM (IC50) DYRK1a:4.36 μM (IC50) DYRK2:0.99 μM (IC50) DYRK3:5.3 μM (IC50) PKD1:5.9 μM (IC50) CDK2:14 μM (IC50) References [1]. De Moliner E, et al. Alternative binding modes of an inhibitor to two different kinases. Eur J Biochem. 2003 Aug;270(15):3174-81. [2]. Orzechowska E, et al. Time schedule-dependent effect of the CK2 inhibitor TBB on PC-3 human prostate cancer cell viability. Oncol Rep. 2012 Jan;27(1):281-5. [3]. Sarno S, et al. Selectivity of 4,5,6,7-tetrabromobenzotriazole, an ATP site-directed inhibitor of protein kinase CK2 ('casein kinase-2'). FEBS Lett. 2001 May 4;496(1):44-8. [4]. Ljubimov AV, et al. Involvement of protein kinase CK2 in angiogenesis and retinal neovascularization. Invest Ophthalmol Vis Sci. 2004 Dec;45(12):4583-91. [5]. Pagano MA, et al. The selectivity of inhibitors of protein kinase CK2: an update. Biochem J. 2008 Nov 1;415(3):353-65. [6]. Chen Z, et al. CK2α promotes advanced glycation end products-induced expressions of fibronectin and intercellular adhesion molecule-1 via activating MRTF-A in glomerular mesangial cells. Biochem Pharmacol. 2017 Dec 6;148:41-51. Chemical & Physical Properties Molecular Formula C6HBr4N3 Exact Mass 430.690369 PSA 41.57000 Index of Refraction 1.801 InChIKey OMZYUVOATZSGJY-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified |
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