Desmethylglycitein (Synonyms: 6-hydroxy Daidzein, 6,7,4’-THIF) |
Catalog No.GC38482
One-Click Copy Product Info
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La déméthylglycitéine (4',6,7-trihydroxyisoflavone), un métabolite de la daidzéine, provenant de Glycine max avec des activités antioxydantes et anticancéreuses. La déméthylglycitéine se lie directement À CDK1 et CDK2 in vivo, ce qui supprime l'activité de CDK1 et CDK2. La desméthylglycitéine est un inhibiteur direct de la protéine kinase C (PKC) α, contre la métalloprotéinase matricielle 1 (MMP1) induite par les UV solaires (sUV). La desméthylglycitéine se lie À PI3K de manière compétitive avec l'ATP dans le cytosol, oÙ elle inhibe l'activité de PI3K et des cascades de signalisation en aval, entraÎnant la suppression de l'adipogenèse dans les préadipocytes 3T3-L1.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 17817-31-1
Sample solution is provided at 25 µL, 10mM.
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Desmethylglycitein, a metabolite of daidzein, is a potent tyrosinase inhibitor with an IC50 value of 9.2μM for mushroom tyrosinase [1]. Desmethylglycitein inhibits the development of Aedes aegypti larvae by strongly suppressing the activity of glutathione S-transferase Noppera-bo, with an IC50 value of 0.287μM[2]. Desmethylglycitein simultaneously reduces Pin1 isomerase activity and the downstream activation targets of Pin1 to suppress esophageal cancer growth [3]. Desmethylglycitein has been widely used to inhibit neuronal cell death and alleviate oxidative stress[4].
In vitro, Desmethylglycitein treatment for 72 hours significantly inhibited the proliferation of MCF10CA1a cells, with an IC50 value of 12.4μM [5]. Treatment with 80μM Desmethylglycitein for 8 days significantly inhibited adipogenesis in 3T3-L1 preadipocytes and reduced the expression of PPAR-γ and C/EBP-α[6].
In vivo, Desmethylglycitein treatment via a single oral dose of 5mg/kg improved the cognitive impairment caused by scopolamine in mice within one hour, and enhanced the learning and memory abilities in the Y-maze test[7]. Intraperitoneal injection of 25mg/kg dose of Desmethylglycitein was administered every other day for 20 days, which significantly inhibited the growth of HCT-116 xenograft tumors in mice and reduced the activities of CDK1 and CDK2 within the tumors[8].
References:
[1] Chang T S, Ding H Y, Lin H C. Identifying 6, 7, 4′-trihydroxyisoflavone as a potent tyrosinase inhibitor[J]. Bioscience, biotechnology, and biochemistry, 2005, 69(10): 1999-2001.
[2] Inaba K, Ebihara K, Senda M, et al. Molecular action of larvicidal flavonoids on ecdysteroidogenic glutathione S-transferase Noppera-bo in Aedes aegypti[J]. BMC biology, 2022, 20(1): 43.
[3] Lim T G, Lee S Y, Duan Z, et al. The prolyl isomerase Pin1 is a novel target of 6, 7, 4′-trihydroxyisoflavone for suppressing esophageal cancer growth[J]. Cancer Prevention Research, 2017, 10(5): 308-318.
[4] Ko Y H, Kwon S H, Kim S K, et al. Protective effects of 6, 7, 4′-trihydroxyisoflavone, a major metabolite of daidzein, on 6-hydroxydopamine-induced neuronal cell death in SH-SY5Y human neuroblastoma cells[J]. Archives of Pharmacal Research, 2019, 42(12): 1081.
[5] Lee J H, Lee H J. A daidzein metabolite, 6, 7, 4′-trihydroxyisoflavone inhibits cellular proliferation through cell cycle arrest and apoptosis induction in MCF10CA1a human breast cancer cells[J]. Journal of the Korean Society for Applied Biological Chemistry, 2013, 56(6): 695-700.
[6] Seo S G, Yang H, Shin S H, et al. A metabolite of daidzein, 6, 7, 4′‐trihydroxyisoflavone, suppresses adipogenesis in 3 T 3‐L 1 preadipocytes via ATP‐competitive inhibition of PI 3 K[J]. Molecular nutrition & food research, 2013, 57(8): 1446-1455.
[7] Ko Y H, Kim S Y, Lee S Y, et al. 6, 7, 4′-Trihydroxyisoflavone, a major metabolite of daidzein, improves learning and memory via the cholinergic system and the p-CREB/BDNF signaling pathway in mice[J]. European Journal of Pharmacology, 2018, 826: 140-147.
[8] Lee D E, Lee K W, Jung S K, et al. 6, 7, 4′-trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2[J]. Carcinogenesis, 2011, 32(4): 629-635.
| Cell experiment [1]: | |
Cell lines | MCF10CA1a cells |
Preparation Method | MCF10CA1a cells were grown in DMEM/F12 medium supplemented with 1% penicillin/streptomycin, 5% horse serum, and HEPES buffer at 37°C in an incubator with 5% CO2. Cells were cultured in 96-well plates in culture medium at 1000 cells/well for 24h. Different concentrations of Desmethylglycitein (0, 1, 10, 20, 50 and 100μM) were added and incubated at 37°C with 5% CO2 for 72h. Cell viability was measured. |
Reaction Conditions | 0, 1, 10, 20, 50 and 100μM; 72h |
Applications | Desmethylglycitein treatment significantly reduced cell viability of MCF10CA1a cells in a dose-dependent manner. |
| Animal experiment [2]: | |
Animal models | Female athymic nude mice |
Preparation Method | Female athymic nude mice (5 weeks old; 20g) were housed in an environmentally controlled room (12h light–dark cycle, 50%±10% relative humidity) at 23±2°C in a facility with free access to food and water. Each mouse was subcutaneously injected with HCT116 cells (2×106cells/200μl) in the left flank and the cells were allowed to form tumors. When tumors reached a size of 100mm3, the mice were randomly assigned to groups (six mice/group) and treated with Desmethylglycitein (25mg/kg) in 50% dimethyl sulfoxide/phosphate-buffered saline buffer, given intraperitoneally every other day for 20 days. Tumor size was measured every other day using calipers and tumor volume. |
Dosage form | 25mg/kg/day; every other day for 20 days; i.p. |
Applications | Desmethylglycitein treatment inhibited tumor growth in mice with HCT-116 xenografts. |
References: | |
| Cas No. | 17817-31-1 | SDF | |
| Synonymes | 6-hydroxy Daidzein, 6,7,4’-THIF | ||
| Canonical SMILES | O=C1C(C2=CC=C(O)C=C2)=COC3=CC(O)=C(O)C=C13 | ||
| Formula | C15H10O5 | M.Wt | 270.24 |
| Solubility | DMSO: 125 mg/mL (462.55 mM) | Storage | Store at 2-8°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 3.7004 mL | 18.5021 mL | 37.0041 mL |
| 5 mM | 740.1 μL | 3.7004 mL | 7.4008 mL |
| 10 mM | 370 μL | 1.8502 mL | 3.7004 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 26 reference(s) in Google Scholar.)