CAS Number301836-41-9
Synonyms4-[4-(1,3-Benzodioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl]benzamide; SB 431542; SB-431542; 4-[4-(1,3-Benzodioxol-5-yl)-5-(2-pyridinyl)-1H-imidazol-2-yl]benzamide; 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzamide
Molecular FormulaC22H16N4O3
Molecular Weight384.39 (anhydrous basis)
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point662.4±55.0 °C at 760 mmHg
Melting Point214 °C(dec.)
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 301836-41-9 |
| Catalog No. | 2A-9090786 |
| Chinese Name | SB431542 |
| Synonyms | 4-[4-(1,3-Benzodioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl]benzamide; SB 431542; SB-431542; 4-[4-(1,3-Benzodioxol-5-yl)-5-(2-pyridinyl)-1H-imidazol-2-yl]benzamide; 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzamide |
| Molecular Formula | C22H16N4O3 |
| Molecular Weight | 384.39 (anhydrous basis) |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 662.4±55.0 °C at 760 mmHg |
| Melting Point | 214 °C(dec.) |
| Appearance | powder |
| Water Solubility | DMSO: 10 mg/mL, soluble |
| Storage Condition | Storage method: -20 °C |
| Application | SB-431542 is a potent and selective ALK5 inhibitor with an IC50 value of 94 nM; it is also a transforming growth factor beta receptor (TGF-β Receptor) inhibitor. |
| HTC | 2934999090 |
| PubChem ID | 24724609 |
| MDL Number | MFCD11045982 |
| SMILES | O.NC(=O)c1ccc(cc1)-c2nc(-c3ccc4OCOc4c3)c([nH]2)-c5ccccn5 |
| InChI | 1S/C22H16N4O3.H2O/c23-21(27)13-4-6-14(7-5-13)22-25-19(20(26-22)16-3-1-2-10-24-16)15-8-9-17-18(11-15)29-12-28-17;/h1-11H,12H2,(H2,23,27)(H,25,26);1H2 |
| InChI Key | WQUIJVKNPYBZOF-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 51111800 |
| Hazard Symbols | transportation |
| MSDS | msds/90786_1_301836_41_9.pdf |
| Bioactivity | SB-431542 is a potent and selective inhibitor of ALK5 with an IC50 value of 94 nM, and is also an inhibitor of TGF-β Receptor. Related Catalog Signaling Pathways >> TGF-beta/Smad >> TGF-β Receptor Research Areas >> Cancer Target IC50: 94 nM (ALK5)[2] In Vitro SB-431542 (1 μM) significantly reduces the TGF-β-induced nuclear accumulation of Smad proteins in A498 cells. SB-431542 inhibits TGF-β1-induced collagen Iα1 and PAI-1 mRNA with IC50 values of 60 and 50 nM, respectively. In addition, SB-431542 inhibits TGF-β1-induced fibronectin mRNA and protein with IC50 values of 62 and 22 nM, respectively[1]. SB-431542 (10 μM) is a selective inhibitor of endogenous activin and TGF-β signaling but has no effect on BMP signaling in NIH 3T3 cells[2]. TRKI, SB-431542, inhibits TGF-beta-induced transcription, gene expression, apoptosis, and growth suppression. SB-431542 attenuates the tumor-promoting effects of TGF-beta, including TGF-beta-induced EMT, cell motility, migration and invasion, and vascular endothelial growth factor secretion in human cancer cell lines. SB-431542 induces anchorage independent growth of cells that are growth-inhibited by TGF-beta, whereas it reduces colony formation by cells that are growth-promoted by TGF-beta[3]. SB-431542 (0.3 μM) inhibits cell proliferation induced by TGF-β in MG63 cells[4]. In Vivo SB-431542 (10 mg/kg, i.p.) decreases lung metastasis but does not significantly alter growth of the primary tumor 4T1 xenograft[5]. Kinase Assay A total of 100,000 cells from each pool of A549 and HT29 are seeded into each well of 12-well plate. Cells are cultured in media containing 0.2% FBS for 18 hours, and then treated with 5 ng/mL TGF-β1 in the presence of SB-431542 (10 µM) in 0.5 mL of media for 24 hours. One hundred μLs of each supernatant media is used for VEGF assay according to the manufacturer's instruction. For TGF-β1 ELISA, 100,000 cells from each pool of A549, VMRC-LCD, and HT29 are seeded into each well of 12-well plates and serum-starved for 20 hours. Cells are then treated with SB-431542 in 0.5 mL of serum-free RPMI media for 24 hours. One hundred μLs of each supernatant media is activated and used for TGF-β1 assay according to the manufacturer's instruction. Cell Assay A498 cells are seeded at 5,000 to 10,000 cells/well in 96-well plates. The cells are serum-deprived for 24 h and then treated with SB-431542 for 48 h to assess the cellular toxicity. Cell viability is determined by incubating cells for 4 h with XTT labeling and electron coupling reagent according to the manufacturer's directions. Live cells with active mitochondria produce an orange-colored product, formazan, which is detected using a plate reader at between A 450 nm and A 500 nm with a reference wavelength greater than 600 nm. The absorbance values correlate with the number of viable cells. Animal Admin Ten thousand 4T1 cells are injected subcutaneously into the second mammary fat pad of 6-week-old Balb/c female mice. Tumors are measured twice weekly, and volume is calculated using the following formula: Volume = width2×length×0.52. Mice are randomly assigned to two treatment groups: control, n = 14 (20% DMSO/80% corn oil); SB-431542-treated, n = 15 (10 mg/kg body weight in 20% DMSO/80% corn oil, administered intraperitoneally three times per week starting one day after tumor cell inoculation. Primary tumors are resected when the volume at day 10 post-injection of 4T1 cells. All mice are monitored daily and euthanized after 4 weeks. The metastases are dissected to snap-freeze for further analysis. References [1]. N. J. Laping, et al. Inhibition of Transforming Growth Factor (TGF)-β1-Induced Extracellular Matrix with a Novel Inhibitor of the TGF-β Type I Receptor Kinase Activity: SB-431542. [2]. Inman GJ, et al. SB-431542 is a potent and specific inhibitor of transforming growth factor-beta superfamily type I activin receptor-like kinase (ALK) receptors ALK4, ALK5, and ALK7. Mol Pharmacol, 2002, 62(1), 65-74. [3]. Halder SK, et al. A specific inhibitor of TGF-beta receptor kinase, SB-431542, as a potent antitumor agent for human cancers. Neoplasia, 2005, 7(5), 509-521. [4]. Matsuyama S, et al. SB-431542 and Gleevec inhibit transforming growth factor-beta-induced proliferation of human osteosarcoma cells. Cancer Res, 2003, 63(22), 7791-7798. [5]. Sato M, et al. Differential Proteome Analysis Identifies TGF-β-Related Pro-Metastatic Proteins in a 4T1 Murine Breast Cancer Model. PLoS One. 2015 May 18;10(5):e0126483. [6]. "Ma J, et al. Growth differentiation factor 11 improves neurobehavioral recovery and stimulates angiogenesis in rats subjected to cerebral ischemia/reperfusion. Brain Res Bull. 2018 Feb 9;139:38-47." Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 662.4±55.0 °C at 760 mmHg Melting Point 214 °C(dec.) Molecular Formula C22H16N4O3 Molecular Weight 384.387 Flash Point 354.4±31.5 °C Exact Mass 384.122253 PSA 103.12000 LogP 4.28 Appearance of Characters powder Vapour Pressure 0.0±2.0 mmHg at 25°C Index of Refraction 1.680 InChIKey FHYUGAJXYORMHI-UHFFFAOYSA-N SMILES NC(=O)c1ccc(-c2nc(-c3ccc4c(c3)OCO4)c(-c3ccccn3)[nH]2)cc1 Storage condition −20°C Water Solubility DMSO: 10 mg/mL, soluble |
| Use of | SB-431542 is a potent and selective inhibitor of ALK5 with an IC50 value of 94 nM, and is also an inhibitor of TGF-β Receptor. Properties Name sb 431542 Synonym More Synonyms SB431542 Biological Activity Description SB-431542 is a potent and selective inhibitor of ALK5 with an IC50 value of 94 nM, and is also an inhibitor of TGF-β Receptor. Related Catalog Signaling Pathways >> TGF-beta/Smad >> TGF-β Receptor Research Areas >> Cancer IC50: 94 nM (ALK5)[2] References [1]. N. J. Laping, et al. Inhibition of Transforming Growth Factor (TGF)-β1-Induced Extracellular Matrix with a Novel Inhibitor of the TGF-β Type I Receptor Kinase Activity: SB-431542. [2]. Inman GJ, et al. SB-431542 is a potent and specific inhibitor of transforming growth factor-beta superfamily type I activin receptor-like kinase (ALK) receptors ALK4, ALK5, and ALK7. Mol Pharmacol, 2002, 62(1), 65-74. [3]. Halder SK, et al. A specific inhibitor of TGF-beta receptor kinase, SB-431542, as a potent antitumor agent for human cancers. Neoplasia, 2005, 7(5), 509-521. [4]. Matsuyama S, et al. SB-431542 and Gleevec inhibit transforming growth factor-beta-induced proliferation of human osteosarcoma cells. Cancer Res, 2003, 63(22), 7791-7798. [5]. Sato M, et al. Differential Proteome Analysis Identifies TGF-β-Related Pro-Metastatic Proteins in a 4T1 Murine Breast Cancer Model. PLoS One. 2015 May 18;10(5):e0126483. [6]. "Ma J, et al. Growth differentiation factor 11 improves neurobehavioral recovery and stimulates angiogenesis in rats subjected to cerebral ischemia/reperfusion. Brain Res Bull. 2018 Feb 9;139:38-47." Chemical & Physical Properties Molecular Formula C22H16N4O3 Exact Mass 384.122253 PSA 103.12000 Appearance of Characters powder Index of Refraction 1.680 InChIKey FHYUGAJXYORMHI-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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