| Size | Price | Stock | Qty |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
Desmethylglycitein directly binds to and inhibits CDK1 and CDK2 in vivo. It also binds to PI3K in an ATP-competitive manner in the cytosol, inhibiting PI3K activity and downstream signaling cascades. Additionally, it is a direct inhibitor of protein kinase C (PKC)α and exhibits inhibitory activity against glutathione S-transferase Noppera-bo.
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| ln Vitro |
In a dose- and time-dependent manner, desmethylglycitein (4',6,7-TriHydroxyisoflavone) (0-100 μM; 24-72 hours) inhibits the anchorage-dependent growth of HCT-116 and DLD1 cells without causing cytotoxicity[1]. In a dose-dependent manner, desmethylglycitein (4',6,7-TriHydroxyisoflavone) (0-100 μM; 24-72 hours) inhibits both CDK1 and CDK2 activity in HCT-116 cells [1]. Cell cycle arrest is induced in S and G2/M phases by desmethylglycitein (4',6,7-TriHydroxyisoflavone) (0-100 μM; 24-72 hours), with a higher percentage of cells in S phase at 100 μM6,7. In the 4'-THIF treatment group, the same pattern was observed in the G2/M phase (29.5% vs. 19.1%) [1].
In vitro, desmethylglycitein (0–100 µM; 24–72 hours) inhibits CDK1 and CDK2 activity in HCT-116 human colon cancer cells in a dose-dependent manner. It significantly inhibits acetylcholinesterase and thiobarbituric acid reactive substance (TBARS) activities. In ex vivo kinase assays using HCT-116 cells, it significantly inhibits cyclin B1/CDK1 and cyclin A/CDK2 complex activities in a dose-dependent manner. |
| ln Vivo |
In addition to acting as a potent anticancer treatment, desmethylglycitein (4',6,7-trihydroxyisoflavone) (ip; 5 or 25 mg/kg; once daily; 20 days) inhibits the growth of tumors in mice and may also prevent or postpone the tumorigenicity of HCT-116 cells in an in vivo system [1].
In vivo, desmethylglycitein binds directly to CDK1 and CDK2, suppressing their activity. It significantly improves scopolamine-induced cognitive dysfunction and enhances learning and memory performance in behavioral tests. It also suppresses adipogenesis in 3T3-L1 preadipocytes via ATP-competitive inhibition of PI3K. |
| Enzyme Assay |
Kinase inhibition assays are performed using recombinant CDK1/cyclin B1 and CDK2/cyclin A complexes. Desmethylglycitein is incubated with the kinase, ATP, and a substrate peptide. Activity is measured by quantifying phosphorylated substrate using scintillation counting or ELISA after separation. For PKCα, activity is measured using a kinase assay kit with a specific substrate peptide, and inhibition is determined by measuring incorporated radioactive phosphate or using a fluorescence-based method.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: HCT-116 Cell Tested Concentrations: 0, 12.5, 25, 50 or 100 μM Incubation Duration: 24, 48 or 72 hrs (hours) Experimental Results: Inhibition of anchorage-dependent and -independent inhibition of HCT-116 cells grow. Western Blot Analysis [1] Cell Types: HCT-116 and DLD1 cells Tested Concentrations: 0, 25, 50 or 100 μM Incubation Duration: 48 hrs (hours) Experimental Results: Inhibition of CDK1 and CDK2 expression. Cell cycle analysis[1] Cell Types: HCT-116 Cell Tested Concentrations: 0, 25, 50 or 100 μM Incubation Duration: 24, 48 or 72 hrs (hours) Experimental Results: Induced cell cycle of HCT-116 cells in S phase and G2/M phase Stagnation. Human HCT-116 colon cancer cells are cultured and treated with desmethylglycitein at concentrations ranging from 0 to 100 µM for 24–72 hours. Cell proliferation is assessed using MTT or CCK-8 assays. For cell cycle analysis, cells are stained with propidium iodide and analyzed by flow cytometry. CDK1 and CDK2 activity in cell lysates is measured using immunoprecipitation followed by kinase assays with histone H1 as substrate. 3T3-L1 preadipocytes are used to study adipogenesis inhibition. |
| Animal Protocol |
Animal/Disease Models: Female athymic nude mice were injected subcutaneously (sc) (sc) with HCT-116 cells [1]
Doses: 5 or 25 mg/kg Route of Administration: intraperitoneal (ip) injection; 5 or 25 mg/kg; one time/day; 20-day Experimental Results: HCT-116 xenogeneic Tumor growth, size, and weight of the grafts were diminished. Scopolamine-induced cognitive dysfunction models in rodents are used. Desmethylglycitein is administered orally or intraperitoneally, and cognitive function is assessed using the Morris water maze or passive avoidance tests. For anticancer activity, HCT-116 human colon cancer xenograft models in nude mice are employed. Tumor volume is measured, and CDK1/CDK2 activity in tumor tissues is analyzed by immunohistochemistry or Western blot. |
| ADME/Pharmacokinetics |
Desmethylglycitein is a small molecule (MW 270.24). As a daidzein metabolite, it is expected to have moderate oral bioavailability, undergoing phase II metabolism (glucuronidation and sulfation) similar to other isoflavones. It likely distributes to various tissues. Detailed PK parameters such as half-life, Cmax, and AUC are not well characterized in the literature.
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| Toxicity/Toxicokinetics |
Desmethylglycitein is generally considered safe at pharmacological doses based on its natural origin as a dietary isoflavone metabolite. No significant acute toxicity has been reported in animal studies at doses used for cognitive improvement or anticancer efficacy. It has antioxidant properties and may offer protective effects against oxidative stress. Comprehensive toxicological profiles, including chronic toxicity and genotoxicity, are not extensively documented.
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| References |
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| Additional Infomation |
4',6,7-Trihydroxyisoflavone is a hydroxyisoflavone, formed by adding a hydroxyl substituent at the 6-position to daidzein. It possesses multiple functions, including as a metabolite, PPARα agonist, PPARγ agonist, anti-inflammatory agent, antimutagenic agent, and EC 1.14.18.1 (tyrosinase) inhibitor. Its functions are related to daidzein. 6,7,4'-Trihydroxyisoflavone has been reported to be present in chili peppers (Capsicum annuum), and relevant data are available.
Desmethylglycitein is primarily used as a research tool to study cell cycle regulation, cancer biology, and adipogenesis. Its mechanism involves multi-target inhibition of CDK1, CDK2, PKCα, and PI3K. It is not an approved drug and is not in clinical trials. It serves as a valuable reference compound for studying the biological activities of isoflavone metabolites. |
| Molecular Formula |
C15H10O5
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|---|---|
| Molecular Weight |
270.2369
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| Exact Mass |
270.053
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| CAS # |
17817-31-1
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| PubChem CID |
5284649
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.548g/cm3
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| Boiling Point |
587.1ºC at 760mmHg
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| Melting Point |
322 °C
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| Flash Point |
229.7ºC
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| Vapour Pressure |
2.21E-14mmHg at 25°C
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| Index of Refraction |
1.732
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| LogP |
2.576
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
20
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| Complexity |
411
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
GYLUFQJZYAJQDI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-14-6-13(18)12(17)5-10(14)15(11)19/h1-7,16-18H
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| Chemical Name |
6,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~462.55 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.70 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (7.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (7.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7004 mL | 18.5021 mL | 37.0041 mL | |
| 5 mM | 0.7401 mL | 3.7004 mL | 7.4008 mL | |
| 10 mM | 0.3700 mL | 1.8502 mL | 3.7004 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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