Desmethylglycitein (Synonyms: 6-hydroxy Daidzein, 6,7,4’-THIF) |
Katalog-Nr.GC38482
One-Click Copy Product Info
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Desmethylglycitein (4',6,7-Trihydroxyisoflavone), ein Metabolit von Daidzein, der aus Glycine max gewonnen wird, mit antioxidativer und Anti-Krebs-AktivitÄt. Desmethylglycitein bindet in vivo direkt an CDK1 und CDK2, was zur UnterdrÜckung der CDK1- und CDK2-AktivitÄt fÜhrt. Desmethylglycitein ist ein direkter Inhibitor der Proteinkinase C (PKC)α gegen die durch solares UV (sUV) induzierte Matrix-Matrix-Metalloproteinase 1 (MMP1). Desmethylglycitein bindet an PI3K in ATP-kompetitiver Weise im Zytosol, wo es die AktivitÄt von PI3K und nachgeschalteten Signalkaskaden hemmt, was zur UnterdrÜckung der Adipogenese in 3T3-L1-PrÄadipozyten fÜhrt.
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 | |
| Überlieferungen | 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 |
| Löslichkeit | 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 | |||
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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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Quality Control & SDS
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- Purity: >98.00% Appearance: A solid
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Average Rating: 5 (Based on Reviews and 26 reference(s) in Google Scholar.)