| Field | Specification |
|---|---|
| Target | |
| Alternative names | Indirubin-3'-oxime |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C16H11N3O2 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Indirubin-3'-monoxime, also known as Indirubin-3'-oxime, is a potent inhibitor of GSK-3β and a weak inhibitor of 5-Lipoxygenase, with IC50 values of 22 nM and 7.8-10 μM, respectively. It also inhibits CDK5/p25 and CDK1/cyclin B, with IC50 values of 100 nM and 180 nM. It is supplied as a brown to red solid (C16H11N3O2, MW 277.28) at 99.80% purity.
Physical & Chemical Properties
| CAS Number | 160807-49-8 |
|---|---|
| Molecular Formula | C16H11N3O2 |
| Molecular Weight | 277.28 g/mol |
| Purity | 99.80% |
| Appearance | Solid |
| Color | Brown to red |
| SMILES | O=C1NC2=C(C=CC=C2)/C1=C3NC4=C(C=CC=C4)C\3=N/O |
| Target | GSK-3β, CDK5/p25, CDK1/cyclin B, 5-LOX |
| Signaling Pathway | PI3K/Akt/mTOR; Stem Cell/Wnt; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease |
| Solubility | In Vitro: DMSO: 125 mg/mL (450.81 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 2 years; -20°C, 1 year. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Biological Activity
IC50 & Target
[1][3]
|
GSK-3β 22 nM (IC50) |
CDK5/p25 100 nM (IC50) |
CDK1/cyclin B 180 nM (IC50) |
5-LOX 7.8-10 μM (IC50) |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 125 mg/mL (450.81 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 2 years) or -20°C (up to 1 year); avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | ≥ 2.5 mg/mL (9.02 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Data provided by the manufacturer.
In Vitro
Indirubin-3'-monoxime competes with ATP to inhibit GSK-3β, with a Ki of 0.85 μM and a Km of 110 μM. Indirubin-3'-monoxime also blocks GSK-3β-mediated tau phosphorylation, with an IC50 value of around 100 nM, and completely inhibits phosphorylation of the AT100 epitope[1]. Proliferation of vascular smooth muscle cells (VSMC) is inhibited by Indirubin-3'-monoxime, with an IC50 of ～2 μM. Indirubin-3'-monoxime reduces migration of VSMC stimulated with PDGF, interferes with the migratory response of VSMC, and also suppresses production of pro-migratory LT in monocytes. In addition, Indirubin-3'-monoxime inhibits 5-lipoxygenase (5-LO) product synthesis in monocytes and neutrophils with equal potency (IC50=5.0±1.1 and 3.7±1.2 μM, respectively). In cell-free assay, Indirubin-3'-monoxime inhibits 5-LO with an IC50 of 7.8-10 μM[3].
In Vivo
In HFD fed mice, Indirubin-3'-monoxime (0.1, 0.2 and 0.4 mg/kg, i.p) reverses cognitive impairment and counters elevated oxidative stress markers in a dose dependent manner. Indirubin-3'-monoxime also lowers serum glucose, TGs, TC and insulin levels dose dependently, and improves β-cell functioning in HFD fed mice. Furthermore, Indirubin-3'-monoxime treatment significantly decreases HOMA-IR levels versus the HFD group. Indirubin-3'-monoxime (0.4 mg/kg) significantly attenuates the elevated EL in the HFD group[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
Cell Assay[3]
Assess Indirubin-3'-monoxime cytotoxicity in monocytes by MTT assay in a 96-well format with a multi-well scanning spectrophotometer. Incubate neutrophils (5×106 cells/mL) or monocytes (2×106 cells/mL) with Indirubin-3'-monoxime for 30 min, then analyze cell viability by MTT assay. Relative to vehicle (0.3% DMSO), neither cell type shows significant acute cytotoxicity (neutrophils: 103.9±4.4%; monocytes: 129.4±5.4%; n=3, each)[3].
Animal Administration[2]
Randomly assign male mice (5-6 weeks old) to five groups (n=10). Group 1: normal pellet diet (NPD); Group 2: HFD; Group 3-5: HFD for 8 weeks, then Indirubin-3'-monoxime (0.1, 0.2 and 0.4 mg/kg i.p, respectively), given once daily for 1 week. Dissolve Indirubin-3'-monoxime in DMSO (2.5% v/v) in saline. Give the NPD and HFD groups an equal volume of vehicle (2.5% v/v DMSO in saline). Select the Indirubin-3'-monoxime doses. Maintain the mice for 8 weeks under standard husbandry conditions (22±1°C and 60% humidity), a 12/12-h light/dark schedule, and free access to food and water. Record body weight weekly throughout the experimental period[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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A novel indirubin- 3-monoxime derivative I3MV- 8b exhibits remarkable cytotoxicity against multiple myeloma by targeting TRIM28. Biomark Res 2025 Apr 7;13(1):57. PMID: 40197552
CRIP1 involves the pathogenesis of multiple myeloma via dual-regulation of proteasome and autophagy. EBioMedicine 2024 Feb:100:104961. PMID: 38199044
Indirubin-3'-monoxime acts as proteasome inhibitor: Therapeutic application in multiple myeloma. EBioMedicine 2022 Apr;78:103950. PMID: 35344764
Oncosis-like cell death is induced by berberine through ERK1/2-mediated impairment of mitochondrial aerobic respiration in gliomas. Biomed Pharmacother 2018 Jun:102:699-710. PMID: 29604589
