CAS Number280744-09-4
Synonyms3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione; S1075_Selleck; SB 216763; SB216763
Molecular FormulaC19H12Cl2N2O2
Molecular Weight371.22
Purity>98 (HPLC)%
Density1.5±0.1 g/cm3
Boiling Point598.1±50.0 °C at 760 mmHg
Melting Point287-288.6ºC(lit.)
Appearanceorange
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 280744-09-4 |
| Catalog No. | 2A-9056277 |
| Chinese Name | SB 216763 |
| Synonyms | 3-(2,4-Dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione; S1075_Selleck; SB 216763; SB216763 |
| Molecular Formula | C19H12Cl2N2O2 |
| Molecular Weight | 371.22 |
| Purity | >98 (HPLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 598.1±50.0 °C at 760 mmHg |
| Melting Point | 287-288.6ºC(lit.) |
| Appearance | orange |
| Water Solubility | DMSO: 20 mg/mL, soluble |
| Storage Condition | −20°C |
| Application | SB 216763 is a potent, selective and ATP-competitive GSK-3 inhibitor with an IC50 of 34.3 nM for GSK-3α and GSK-3β. |
| HTC | 2933990090 |
| PubChem ID | 24278616 |
| MDL Number | MFCD09753369 |
| SMILES | Cn1cc(C2=C(C(=O)NC2=O)c3ccc(Cl)cc3Cl)c4ccccc14 |
| InChI | 1S/C19H12Cl2N2O2/c1-23-9-13(11-4-2-3-5-15(11)23)17-16(18(24)22-19(17)25)12-7-6-10(20)8-14(12)21/h2-9H,1H3,(H,22,24,25) |
| InChI Key | JCSGFHVFHSKIJH-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/56277_1_280744_09_4.pdf |
| Bioactivity | SB 216763 is potent, selective and ATP-competitive GSK-3 inhibitor with IC50s of 34.3 nM for both GSK-3α and GSK-3β. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Neurological Disease Target GSK-3α:34.3 nM (IC50) GSK-3β:34.3 nM (IC50) In Vitro SB-216763 (10-20 µM) induces β-catenin mediated-transcription in a dose-dependent manner in HEK293 cells. SB-216763 (10, 15 and 20 µM) can maintain mESCs with a pluripotent-like morphology in long-term culture. SB-216763 (10 µM) can maintain J1 mESCs in a pluripotent state for more than a month[2]. SB-216763 inhibits GSK-3 with IC50 of 34 nM[3]. SB-216763 is equally effective at inhibiting human GSK-3α and GSK-3β[5]. In Vivo SB216763 (20 mg/kg, i.v.) significantly improves the survival of BLM-treated mice. Mice randomized to receive BLM plus SB216763 shows a noteworthy reduction, compared with BLM-treated mice. SB216763 (20 mg/kg, i.v.) reduces the magnitude of BLM-induced alveolitis[1]. SB 216763 (0.2 mg/kg, i.v.) with either 17β-E100 or Geni100 reverses the ceiling effect because these agents significantly reduce infarct size when the rabbits' hearts are submitted to 30-min CAO[4]. Cell Assay MESCs maintained with LIF or 10 µM SB-216763 for more than a month are resuspended at 40,000 cells/mL in LIF-free mESC medium. EBs are prepared by a hanging drop procedure. Briefly, 20 µL drops containing mESCs are pipetted on the inside of a 10-cm Petri dish lid. The lids are placed onto Petri dishes containing 10 mL of HBSS and the EBs are allowed to form and grow for 4 days in the incubator. After 4 days, 15-20 EBs are transferred to a well containing LIF-free mESC medium in a 24-well plate. The medium is exchanged every two days and autonomously beating cell aggregates are observed and counted. Animal Admin Mice are allocated to four groups (n=12/group) as follows: 1) intratracheal saline + vehicle (25% dimethyl sulfoxide, 25% polyethylene glycol, and 50% saline), 2) intratracheal saline + SB216763 (20 mg/kg) dissolved in vehicle, 3) intratracheal BLM (3 U/kg) + vehicle, and 4) intratracheal BLM + SB216763 (20 mg/kg) in vehicle. Another set of experiments to assess cytokine expression by reverse transcription-PCR is conducted in the mice (n=12/group) to receive 1) intratracheal saline + vehicle, 2) intratracheal BLM, and 3) intratracheal BLM + SB216763. To induce pulmonary fibrosis, BLM is intratracheally administered in mice (n=15/group) on day 0. BLM and saline-treated mice are administered with SB216763 dissolved in vehicle or vehicle alone intravenously at day 0 and then intraperitoneally twice a week until day 28. Mice are sacrificed by CO2 inhalation on days 2, 7, and 28. In the terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL) experiments, the cohorts of mice are as follows: saline-treated (n=6), BLM-treated (n=6), and BLM + SB216763-treated (n=6). References [1]. Gurrieri, et al. 3-(2,4-dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (SB216763), a glycogen synthase kinase-3 inhibitor, displays therapeutic properties in a mouse model of pulmonary inflammation and fibrosis. J.Pharmacol.Exp.Ther.2010 [2]. Kirby LA, et al. Glycogen synthase kinase 3 (GSK3) inhibitor, SB-216763, promotes pluripotency in mouse embryonic stem cells.PLoS One. 2012;7(6):e39329. Epub 2012 Jun 26. [3]. Wang M, et al. The first synthesis of [(11)C]SB-216763, a new potential PET agent for imaging of glycogen synthase kinase-3 (GSK-3).Bioorg Med Chem Lett. 2011 Jan 1;21(1):245-9. Epub 2010 Nov 11. [4]. The ceiling effect of pharmacological postconditioning with the phytoestrogen genistein is reversed by the GSK3beta inhibitor SB 216763 [3-(2,4-dichlorophenyl)-4(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione] through mitochondrial ATP-dependent potassium channel opening. [5]. Coghlan MP, et al. Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription. Chem Biol. 2000 Oct;7(10):793-803. [6]. Wang W, et al. Inhibition of glycogen synthase kinase 3beta ameliorates triptolide-induced acute cardiac injury by desensitizing mitochondrial permeability transition. Toxicol Appl Pharmacol. 2016 Dec 15;313:195-203. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 598.1±50.0 °C at 760 mmHg Melting Point 287-288.6ºC(lit.) Molecular Formula C19H12Cl2N2O2 Molecular Weight 371.217 Flash Point 315.5±30.1 °C Exact Mass 370.027588 PSA 51.10000 LogP 4.79 Appearance of Characters orange Vapour Pressure 0.0±1.7 mmHg at 25°C Index of Refraction 1.702 InChIKey JCSGFHVFHSKIJH-UHFFFAOYSA-N SMILES Cn1cc(C2=C(c3ccc(Cl)cc3Cl)C(=O)NC2=O)c2ccccc21 Storage condition −20°C Water Solubility DMSO: 20 mg/mL, soluble |
| Use of | SB 216763 is potent, selective and ATP-competitive GSK-3 inhibitor with IC50s of 34.3 nM for both GSK-3α and GSK-3β. Properties Articles17 Name 3-(2,4-dichlorophenyl)-4-(1-methylindol-3-yl)pyrrole-2,5-dione Synonym More Synonyms SB216763 Biological Activity Description SB 216763 is potent, selective and ATP-competitive GSK-3 inhibitor with IC50s of 34.3 nM for both GSK-3α and GSK-3β. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Neurological Disease GSK-3α:34.3 nM (IC50) GSK-3β:34.3 nM (IC50) References [1]. Gurrieri, et al. 3-(2,4-dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (SB216763), a glycogen synthase kinase-3 inhibitor, displays therapeutic properties in a mouse model of pulmonary inflammation and fibrosis. J.Pharmacol.Exp.Ther.2010 [2]. Kirby LA, et al. Glycogen synthase kinase 3 (GSK3) inhibitor, SB-216763, promotes pluripotency in mouse embryonic stem cells.PLoS One. 2012;7(6):e39329. Epub 2012 Jun 26. [3]. Wang M, et al. The first synthesis of [(11)C]SB-216763, a new potential PET agent for imaging of glycogen synthase kinase-3 (GSK-3).Bioorg Med Chem Lett. 2011 Jan 1;21(1):245-9. Epub 2010 Nov 11. [4]. The ceiling effect of pharmacological postconditioning with the phytoestrogen genistein is reversed by the GSK3beta inhibitor SB 216763 [3-(2,4-dichlorophenyl)-4(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione] through mitochondrial ATP-dependent potassium channel opening. [6]. Wang W, et al. Inhibition of glycogen synthase kinase 3beta ameliorates triptolide-induced acute cardiac injury by desensitizing mitochondrial permeability transition. Toxicol Appl Pharmacol. 2016 Dec 15;313:195-203. Chemical & Physical Properties Exact Mass 370.027588 PSA 51.10000 Appearance of Characters orange Index of Refraction 1.702 InChIKey JCSGFHVFHSKIJH-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 14.1 UN dangerous goods number 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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