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Desmethylglycitein

Cat No.:V32261 Purity: ≥98%
Desmethylglycitein (4',6,7-Trihydroxyisoflavone), a metabolite of daidzein, developed from soybean Glycine max, has antioxidant and anticancer activities.
Desmethylglycitein
Desmethylglycitein Chemical Structure CAS No.: 17817-31-1
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
Other Sizes
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Product Description
Desmethylglycitein (4',6,7-Trihydroxyisoflavone), a metabolite of daidzein, developed from soybean Glycine max, has antioxidant and anticancer activities. Desmethylglycitein directly binds CDK1 and CDK2 in vivo and inhibits CDK1 and CDK2 activities. Desmethylglycitein is a direct inhibitor of protein kinase C (PKC)α and inhibits solar ultraviolet (sUV)-induced matrix metalloproteinase 1 (MMP1) in normal human skin fibroblasts. Desmethylglycitein binds to PI3K in the cytoplasm in an ATP competitive manner, inhibits the activity of PI3K and downstream signaling cascades, and thereby inhibits adipogenesis in 3T3-L1 preadipocytes.
Biological Activity I Assay Protocols (From Reference)
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].
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].
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.
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.
References

[1]. 6,7,4'-trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2. Carcinogenesis. 2011 Apr;32(4):629-35.

[2]. The daidzein metabolite, 6,7,4'-Trihydroxyisoflavone, is a novel inhibitor of PKCα in suppressing solar UV-induced matrix metalloproteinase 1. Int J Mol Sci. 2014 Nov 19;15(11):21419-32.

[3]. A metabolite of daidzein, 6,7,4'-trihydroxyisoflavone, suppresses adipogenesis in 3T3-L1 preadipocytes via ATP-competitive inhibition of PI3K.

Additional Infomation
4',6,7-trihydroxyisoflavone is a hydroxyisoflavone that is daidzein bearing an additional hydroxy substituent at position 6. It has a role as a metabolite, a PPARalpha agonist, a PPARgamma agonist, an anti-inflammatory agent, an antimutagen and an EC 1.14.18.1 (tyrosinase) inhibitor. It is functionally related to a daidzein.
6,7,4'-Trihydroxyisoflavone has been reported in Capsicum annuum with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O5
Molecular Weight
270.2369
Exact Mass
270.053
CAS #
17817-31-1
PubChem CID
5284649
Appearance
Light yellow to yellow solid powder
Density
1.548g/cm3
Boiling Point
587.1ºC at 760mmHg
Melting Point
322 °C
Flash Point
229.7ºC
Vapour Pressure
2.21E-14mmHg at 25°C
Index of Refraction
1.732
LogP
2.576
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Heavy Atom Count
20
Complexity
411
Defined Atom Stereocenter Count
0
InChi Key
GYLUFQJZYAJQDI-UHFFFAOYSA-N
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
Chemical Name
6,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~462.55 mM)
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.

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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.
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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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