![(2E,3E)-3-(HYDROXYIMINO)-[2,3'-BIINDOLINYLIDENE]-2'-ONE structure, CAS 160807-49-8](/structures/100000/95049_1_160807_49_8.png)
CAS Number160807-49-8
Synonyms3-(Hydroxyamino)-1H,2'H-2,3'-biindol-2'-one; (3Z)-3-[(3E)-3-(Hydroxyimino)-1,3-dihydro-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one; Indirubin-3'-oxime; MFCD02683594; Indirubin-3'-monoxime
Molecular FormulaC16H11N3O2
Molecular Weight277.28
Purity≥98 (HPLC)%
Density1.5±0.1 g/cm3
Boiling Point532.2±50.0 °C at 760 mmHg
Melting Point241 °C
Appearancesolid
EINECS0
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 160807-49-8 |
| Catalog No. | 2A-0095049 |
| Chinese Name | 靛玉红-3'-单肟 |
| Synonyms | 3-(Hydroxyamino)-1H,2'H-2,3'-biindol-2'-one; (3Z)-3-[(3E)-3-(Hydroxyimino)-1,3-dihydro-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one; Indirubin-3'-oxime; MFCD02683594; Indirubin-3'-monoxime |
| Molecular Formula | C16H11N3O2 |
| Molecular Weight | 277.28 |
| Purity | ≥98 (HPLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 532.2±50.0 °C at 760 mmHg |
| Melting Point | 241 °C |
| Appearance | solid |
| Storage Condition | -20°C; store under inert gas; protect from light, |
| Application | Indirubin-3'-monoxime is a potent GSK-3β inhibitor with weak inhibitory effect on 5-Lipoxygenase, with IC50 values of 22 nM and 7.8-10 µM respectively; Indirubin-3'-monoxime also has strong effects |
| EINECS | 0 |
| HTC | 2933990090 |
| UN(IATA) | 0 |
| PubChem ID | 24278483 |
| MDL Number | MFCD02683594 |
| SMILES | O\N=C1\C(Nc2ccccc12)=C3\C(=O)Nc4ccccc34 |
| InChI | 1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+ |
| InChI Key | HBDSHCUSXQATPO-BGBJRWHRSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/95049_1_160807_49_8.pdf |
| Bioactivity | Indirubin-3'-monoxime is a potent GSK-3β inhibitor, and weakly inhibits 5-Lipoxygenase, with IC50s of 22 nM and 7.8-10 µM, respectively; Indirubin-3'-monoxime also shows inhibitory activities against CDK5/p25 and CDK1/cyclin B, with IC50s of 100 and 180 nM. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Cancer Target GSK-3β:22 nM (IC50) CDK5/p25:100 nM (IC50) CDK1/cyclin B:180 nM (IC50) 5-Lipoxygenase:7.8-10 μM (IC50) In Vitro Indirubin-3'-monoxime inhibits GSK-3β by competing with ATP, with Ki of 0.85 μM, and Km of 110 μM. Indirubin-3'-monoxime also inhibits tau phosphorylation by GSK-3β, with an IC50 value of around 100 nM. Indirubin-3'-monoxime completely inhibits the phosphorylation of the AT100 epitope[1]. Indirubin-3'-monoxime inhibits vascular smooth muscle cell (VSMC) proliferation with IC50 of ∼2 µM. Indirubin-3'-monoxime blunts migration of VSMC stimulated with the PDGF. Indirubin-3'-monoxime interferes with the migratory response in VSMC, and also suppresses the production of pro-migratory LT in monocytes. Moreover, Indirubin-3'-monoxime inhibits 5-lipoxygenase (5-LO) product synthesis in monocytes and neutrophils, with the same potency (IC50=5.0±1.1 and 3.7±1.2 µM, respectively). Indirubin-3'-monoxime is an inhibitor of 5-LO, with IC50 of 7.8-10 µM in cell-free assay[3]. In Vivo Indirubin-3'-monoxime (0.1, 0.2 and 0.4 mg/kg, i.p) dose dependently reverses the cognitive impairment and combats the elevated oxidative stress markers in HFD fed mice. Indirubin-3'-monoxime also dose dependently lowers the serum glucose, TGs, TC and insulin levels, and improves the β-cell functioning in HFD fed mice. Moreover, Indirubin-3'-monoxime treatment significantly decreases HOMA-IR levels compared to HFD group. Indirubin-3'-monoxime (0.4 mg/kg) significantly attenuates the increased EL in the HFD group[2]. Kinase Assay GSK-3β is expressed in and purified from insect Sf9 cells. It is assayed, following a 1/100 dilution in 1 mg/mL BSA, 10 mM DTT, with 5 μL of 40 μM GS-1 peptide as a substrate, in buffer A, in the presence of 15 μM[γ-32P]ATP (3000 Ci/mmol; 1 mCi/mL) in a final volume of 30 μL. After 30-min incubation at 30°C, 25-μL aliquots of supernatant are spotted onto 2.5×3-cm pieces of Whatman P81 phosphocellulose paper, and, 20 s later, the filters are washed five times (for at least 5 min each time) in a solution of 10 mL of phosphoric acid/liter of water. The wet filters are counted in the presence of 1 mL of ACS scintillation fluid[1]. Cell Assay Cytotoxicity of Indirubin-3'-monoxime in monocytes is analysed by MTT assay in a 96-well format using a multi-well scanning spectrophotometer. Neutrophils (5×106 cells/mL) or monocytes (2×106 cells/mL) are incubated for 30 min with Indirubin-3'-monoxime, and the viability of the cells is analysed by MTT assay. Compared with vehicle (0.3% DMSO), no significant acute cytotoxicity is observed (neutrophils: 103.9±4.4%; monocytes: 129.4±5.4%; n=3, each)[3]. Animal Admin Male mice (5-6 weeks old) are randomLy assigned into five groups (n=10). Group 1: receive normal pellet diet (NPD); Group 2: receive a HFD; Group 3-5 receive HFD for 8 weeks followed by Indirubin-3'-monoxime treatment (0.1, 0.2 and 0.4 mg/kg i.p, respectively) once daily for 1 week. Indirubin-3'-monoxime is dissolved in (2.5% v/v) DMSO in saline. The mice in NPD and HFD groups receive an equivalent volume of vehicle (2.5% v/v DMSO in saline). Doses of Indirubin-3'-monoxime are selected. Mice are kept under standard husbandry conditions (22±1°C and 60% humidity) and maintained on a 12/12-h light/dark schedule with free access to food and water for 8 weeks. Body weight is recorded weekly throughout the experimental period[2]. References [1]. Leclerc S, et al. Indirubins inhibit glycogen synthase kinase-3 beta and CDK5/p25, two protein kinases involved in abnormal tau phosphorylation in Alzheimer's disease. A property common to most cyclin-dependent kinase inhibitors? J Biol Chem. 2001 Jan 5;276(1):251-60. [2]. Sharma S, et al. Neuroprotective role of Indirubin-3'-monoxime, a GSKβ inhibitor in high fat diet induced cognitive impairment in mice. Biochem Biophys Res Commun. 2014 Oct 3;452(4):1009-15. [3]. Blazevic T, et al. Indirubin-3'-monoxime exerts a dual mode of inhibition towards leukotriene-mediated vascular smooth muscle cell migration. Cardiovasc Res. 2014 Mar 1;101(3):522-32. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 532.2±50.0 °C at 760 mmHg Melting Point 241 °C Molecular Formula C16H11N3O2 Molecular Weight 277.277 Flash Point 275.7±30.1 °C Exact Mass 277.085114 PSA 73.72000 LogP 1.08 Vapour Pressure 0.0±1.5 mmHg at 25°C Index of Refraction 1.772 InChIKey FQCPPVRJPILDIK-UHFFFAOYSA-N SMILES O=Nc1c(-c2c(O)[nH]c3ccccc23)[nH]c2ccccc12 |
| Use of | Properties Name Indirubin-3'-monoxime Synonym More Synonyms Indirubin-3'-monoxime Biological Activity Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Cancer GSK-3β:22 nM (IC50) 5-Lipoxygenase:7.8-10 μM (IC50) References [2]. Sharma S, et al. Neuroprotective role of Indirubin-3'-monoxime, a GSKβ inhibitor in high fat diet induced cognitive impairment in mice. Biochem Biophys Res Commun. 2014 Oct 3;452(4):1009-15. [3]. Blazevic T, et al. Indirubin-3'-monoxime exerts a dual mode of inhibition towards leukotriene-mediated vascular smooth muscle cell migration. Cardiovasc Res. 2014 Mar 1;101(3):522-32. Chemical & Physical Properties Molecular Formula C16H11N3O2 Exact Mass 277.085114 PSA 73.72000 Index of Refraction 1.772 InChIKey FQCPPVRJPILDIK-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 0.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: No dangerous goods IMDG Code: No dangerous goods International Air Transport Dangerous Regulations: No 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 Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special precautions for users No data available |
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