Name | (2'Z,3'E)-6-Bromoindirubin-3'-oxime |
Synonyms | BIO 6BIO CS-1934 GSK-3 Inhibitor IX (BIO) (2'Z,3'E)-6-Bromoindirubin-3'-oxim (2'Z,3'E)-6-Bromoindirubin-3'-oxime 2H-Indol-2-one, 6-broMo-3-[(3E)-1,3-dihydro-3-(hydroxyiMino)-2H-indol-2-ylidene]-1,3-dihydro-, (3Z)- |
CAS | 667463-62-9 |
Molecular Formula | C16H10BrN3O2 |
Molar Mass | 356.17 |
Density | 1.80±0.1 g/cm3(Predicted) |
Melting Point | 300°C(lit.) |
Boling Point | 554.3±50.0 °C(Predicted) |
Solubility | DMSO 71 mg/mL Water <1 mg/mL Ethanol 21 mg/mL |
Appearance | solid |
Color | dark red |
pKa | 9.56±0.20(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months. |
Sensitive | Air & Light Sensitive |
MDL | MFCD08705318 |
In vitro study | BIO (6-bromoindiirubin-3 '-oxime) is a specific GSK-3 inhibitor, acting on GSK-3α/β with an IC50 of 5 nM, which is more than 16 times more selective than cdk5. BIO interacts with the ATP-binding pocket of these kinases to reduce β-catenin phosphorylation at GSK-3-specific sites. BIO acts on human and mouse embryonic stem cells to maintain the undifferentiated phenotype and maintain the expression of the pluripotent state-specific transcription factors Oct-3/4, Rex-1 and Nanog. BIO-mediated activation of Wnt signaling is functionally reversible, resulting in normal pluripotent differentiation programs in human and mouse embryonic stem cells after withdrawal of the compound. BIO promotes mammalian cardiomyocyte proliferation. BIO is also a pan-JAK inhibitor, acting on TYK2, JAK1, JAK2 and JAK3 with IC50 values of 0.03, 1.5, 8.0 and 0.5 μm respectively. BIO selectively inhibits STAT3 phosphorylation and induces apoptosis in human melanoma cells. |
In vivo study | BIO-treated mouse xenograft model inhibits melanoma growth. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
WGK Germany | 3 |
RTECS | NM3241900 |
HS Code | 29339900 |
Reference Show more | 1. Liu, C., Tang, X., Zhang, W. et al. 6-Bromoindirubin-3′-Oxime Suppresses LPS-Induced Inflammation via Inhibition of the TLR4/NF-κB and TLR4/MAPK Signaling Pathways. Inflammation 42, 2192–2204 (2019). https://doi.org/10.1007/s10753-019-01083-1 2. [IF=3.212] Chang Liu et al."6-Bromoindirubin-3′-Oxime Suppresses LPS-Induced Inflammation via Inhibition of the TLR4/NF-κB and TLR4/MAPK Signaling Pathways."Inflammation. 2019 Dec;42(6):2192-2204 |
biological activity | BIO (GSK-3 Inhibitor IX, 6-bromoindirubin-3-oxime, 6-bromoindirubin-3 '-oxime, MLS 2052) is a specific GSK-3 inhibitor. IC50 acting on GSK-3α/β in cell-free test is 5 nM, which is more than 16 times higher than that acting on CDK5. It is also a pan-JAK inhibitor, the IC50 value for Tyk2 is 30 nM. BIO induces apoptosis in human melanoma cells. |
Target | Value |
GSK-3 (Cell-free assay) | 5 nM |
TYK2 (Cell-free assay) | 30 nM |
CDK5/p35 (Cell-free assay) | 0.08 μM |
CDK2/CyclinA (Cell-free assay) | 0.30 μM |
CDK1/CyclinB (Cell-free assay) | 0.32 μM |