BIO-acetoximeCAS# 667463-85-6 |
Quality Control & MSDS
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| Cas No. | 667463-85-6 | SDF | Download SDF |
| PubChem ID | 24906283 | Appearance | Powder |
| Formula | C18H12BrN3O3 | M.Wt | 398.21 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 20.83 mg/mL (52.31 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble) | ||
| Chemical Name | [[2-(6-bromo-2-oxo-1H-indol-3-ylidene)indol-3-yl]amino] acetate | ||
| SMILES | CC(=O)ONC1=C2C=CC=CC2=NC1=C3C4=C(C=C(C=C4)Br)NC3=O | ||
| Standard InChIKey | ORWSYHWTBSHFIV-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C18H12BrN3O3/c1-9(23)25-22-16-12-4-2-3-5-13(12)20-17(16)15-11-7-6-10(19)8-14(11)21-18(15)24/h2-8,22H,1H3,(H,21,24) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Selective GSK-3α/β inhibitor (IC50 values are 0.01, 2.4, 4.3 and 63 μM for GSK-3α/β, CDK5/p25, CDK2/cyclin A and CDK1/cyclin B respectively). Induces Wnt signaling and inhibits CD8+ T cell effector differentiation. |
BIO-acetoxime Dilution Calculator
BIO-acetoxime Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.5112 mL | 12.5562 mL | 25.1124 mL | 50.2248 mL | 62.7809 mL |
| 5 mM | 0.5022 mL | 2.5112 mL | 5.0225 mL | 10.045 mL | 12.5562 mL |
| 10 mM | 0.2511 mL | 1.2556 mL | 2.5112 mL | 5.0225 mL | 6.2781 mL |
| 50 mM | 0.0502 mL | 0.2511 mL | 0.5022 mL | 1.0045 mL | 1.2556 mL |
| 100 mM | 0.0251 mL | 0.1256 mL | 0.2511 mL | 0.5022 mL | 0.6278 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Antiherpetic potential of 6-bromoindirubin-3'-acetoxime (BIO-acetoxime) in human oral epithelial cells.[Pubmed:23392633]
Arch Virol. 2013 Jun;158(6):1287-96.
Glycogen synthase kinase 3 (GSK-3) functions in the regulation of glycogen metabolism, in the cell cycle, and in immune responses and is targeted by some viruses to favor the viral life cycle. Inhibition of GSK-3 by 6-bromoindirubin-3'-acetoxime (BIO-acetoxime), a synthetic derivative of a compound from the Mediterranean mollusk Hexaplex trunculus, protects cells from varicella infection. In this study, we examined the effects of BIO-acetoxime against herpes simplex virus-1 (HSV-1) infection in human oral epithelial cells, which represent a natural target cell type. The results revealed that BIO-acetoxime relieves HSV-1-induced cytopathic effects and apoptosis. We also found that BIO-acetoxime reduced viral yields and the expression of different classes of viral proteins. Furthermore, addition of BIO-acetoxime before, simultaneously with or after HSV-1 infection significantly reduced viral yields. Collectively, BIO-acetoxime may suppress viral gene expression and protect oral epithelial cells from HSV-1 infection. These results suggest the possible involvement of GSK-3 in HSV-1 infection.
Wnt signaling arrests effector T cell differentiation and generates CD8+ memory stem cells.[Pubmed:19525962]
Nat Med. 2009 Jul;15(7):808-13.
Self-renewing cell populations such as hematopoietic stem cells and memory B and T lymphocytes might be regulated by shared signaling pathways. The Wnt-beta-catenin pathway is an evolutionarily conserved pathway that promotes hematopoietic stem cell self-renewal and multipotency by limiting stem cell proliferation and differentiation, but its role in the generation and maintenance of memory T cells is unknown. We found that induction of Wnt-beta-catenin signaling by inhibitors of glycogen sythase kinase-3beta or the Wnt protein family member Wnt3a arrested CD8(+) T cell development into effector cells. By blocking T cell differentiation, Wnt signaling promoted the generation of CD44(low)CD62L(high)Sca-1(high)CD122(high)Bcl-2(high) self-renewing multipotent CD8(+) memory stem cells with proliferative and antitumor capacities exceeding those of central and effector memory T cell subsets. These findings reveal a key role for Wnt signaling in the maintenance of 'stemness' in mature memory CD8(+) T cells and have major implications for the design of new vaccination strategies and adoptive immunotherapies.
Structural basis for the synthesis of indirubins as potent and selective inhibitors of glycogen synthase kinase-3 and cyclin-dependent kinases.[Pubmed:14761195]
J Med Chem. 2004 Feb 12;47(4):935-46.
Pharmacological inhibitors of glycogen synthase kinase-3 (GSK-3) and cyclin-dependent kinases have a promising potential for applications against several neurodegenerative diseases such as Alzheimer's disease. Indirubins, a family of bis-indoles isolated from various natural sources, are potent inhibitors of several kinases, including GSK-3. Using the cocrystal structures of various indirubins with GSK-3beta, CDK2 and CDK5/p25, we have modeled the binding of indirubins within the ATP-binding pocket of these kinases. This modeling approach provided some insight into the molecular basis of indirubins' action and selectivity and allowed us to forecast some improvements of this family of bis-indoles as kinase inhibitors. Predicted molecules, including 6-substituted and 5,6-disubstituted indirubins, were synthesized and evaluated as CDK and GSK-3 inhibitors. Control, kinase-inactive indirubins were obtained by introduction of a methyl substitution on N1.
GSK-3-selective inhibitors derived from Tyrian purple indirubins.[Pubmed:14700633]
Chem Biol. 2003 Dec;10(12):1255-66.
Gastropod mollusks have been used for over 2500 years to produce the "Tyrian purple" dye made famous by the Phoenicians. This dye is constituted of mixed bromine-substituted indigo and indirubin isomers. Among these, the new natural product 6-bromoindirubin and its synthetic, cell-permeable derivative, 6-bromoindirubin-3'-oxime (BIO), display remarkable selective inhibition of glycogen synthase kinase-3 (GSK-3). Cocrystal structure of GSK-3beta/BIO and CDK5/p25/indirubin-3'-oxime were resolved, providing a detailed view of indirubins' interactions within the ATP binding pocket of these kinases. BIO but not 1-methyl-BIO, its kinase inactive analog, also inhibited the phosphorylation on Tyr276/216, a GSK-3alpha/beta activation site. BIO but not 1-methyl-BIO reduced beta-catenin phosphorylation on a GSK-3-specific site in cellular models. BIO but not 1-methyl-BIO closely mimicked Wnt signaling in Xenopus embryos. 6-bromoindirubins thus provide a new scaffold for the development of selective and potent pharmacological inhibitors of GSK-3.
