| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Targets |
Genistein 8-C-glucoside targets the mitochondrial metabolism and apoptosis pathways. Its primary mechanism of action involves the induction of mitochondrial membrane depolarization, which disrupts the electrochemical gradient across the inner mitochondrial membrane. This depolarization triggers the release of cytochrome c and other pro-apoptotic factors from the mitochondria into the cytosol, activating the caspase cascade and ultimately leading to apoptotic cell death. The compound's action on mitochondria places it within the metabolic enzyme/protease pathway category, specifically affecting mitochondrial function. Unlike its aglycone genistein, which primarily targets tyrosine kinases and estrogen receptors, Genistein 8-C-glucoside appears to exert its cytotoxic effects predominantly through mitochondrial disruption rather than receptor-mediated signaling, although the precise molecular targets within the mitochondrial pathway remain to be fully elucidated.
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| ln Vitro |
In vitro studies have demonstrated that Genistein 8-C-glucoside exhibits significant cytotoxic activity against human cancer cell lines. Research conducted on the human SK-OV-3 ovarian carcinoma cell line showed that the compound induces mitochondrial membrane depolarization and triggers apoptosis. The compound's ability to cause mitochondrial dysfunction is a key feature of its in vitro activity, as it disrupts the normal physiological function of mitochondria in cancer cells. The C-glycoside structure of Genistein 8-C-glucoside distinguishes it from other isoflavone glycosides, and its activity profile suggests that it may have different cellular uptake mechanisms and intracellular targets compared to genistein itself. The compound has been evaluated in various cancer cell models, and its cytotoxicity is attributed to the induction of the intrinsic apoptotic pathway through mitochondrial membrane depolarization.
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| ln Vivo |
In vivo activity data for Genistein 8-C-glucoside are limited, as the compound is predominantly used in in vitro research settings. However, given its structural similarity to genistein and other isoflavones, it may be expected to exhibit systemic bioavailability and biological activity following oral administration in animal models, though the C-glycosidic linkage may affect absorption and metabolism compared to O-glycosides. The compound's primary application remains in cell-based mechanistic studies of apoptosis and mitochondrial function rather than in vivo efficacy studies.
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| Enzyme Assay |
In vitro non-cell enzyme/receptor binding assays for Genistein 8-C-glucoside typically involve mitochondrial membrane potential measurements using isolated mitochondria or mitochondrial preparations. The compound is incubated with isolated mitochondria in the presence of appropriate buffers and substrates, and mitochondrial membrane depolarization is assessed using fluorescent dyes such as JC-1 or tetramethylrhodamine ethyl ester (TMRE). Changes in fluorescence intensity are measured spectrophotometrically or fluorometrically to quantify the extent of membrane depolarization induced by the compound. Dose-response experiments are performed to determine the concentration-dependent effects on mitochondrial function.
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| Cell Assay |
In vitro cell-based assays for Genistein 8-C-glucoside utilize human cancer cell lines such as SK-OV-3 ovarian carcinoma cells cultured in appropriate media supplemented with fetal bovine serum and antibiotics. Cells are seeded in multi-well plates and allowed to attach overnight, then treated with varying concentrations of Genistein 8-C-glucoside for specified incubation periods (typically 24-72 hours). Following treatment, mitochondrial membrane potential is assessed using fluorescent probes such as JC-1 or TMRE, with fluorescence measured by flow cytometry or fluorescence microscopy. Apoptosis is evaluated using Annexin V/PI staining, caspase activity assays, or DNA fragmentation analysis. Cell viability is determined using MTT, CCK-8, or similar colorimetric assays.
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| Animal Protocol |
In vivo animal studies for Genistein 8-C-glucoside are not well documented in the published literature. Based on standard protocols for evaluating isoflavone compounds, potential in vivo studies would involve oral or intraperitoneal administration of the compound to rodent models, followed by assessment of tissue distribution, pharmacokinetic parameters, and biological activity. Xenograft tumor models could be employed to evaluate anticancer efficacy, with tumor volume measurements, histopathological analysis, and assessment of apoptotic markers in tumor tissues. However, specific published in vivo data for this particular compound remain limited.
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| ADME/Pharmacokinetics |
Genistein 8-C-glucoside has a molecular weight of 432.38 g/mol and a molecular formula of C₂₁H₂₀O₁₀. It exhibits a boiling point of 767.7±60.0 °C at 760 mmHg. The compound is soluble in DMSO and other organic solvents, with recommended storage as a powder at -20°C for up to three years or at 4°C for up to two years. As a C-glycoside, it is expected to have greater metabolic stability compared to O-glycosides, potentially leading to improved oral bioavailability. Detailed pharmacokinetic parameters such as half-life, volume of distribution, clearance, and bioavailability have not been extensively characterized in the literature.
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| Toxicity/Toxicokinetics |
The toxicity profile of Genistein 8-C-glucoside has not been comprehensively evaluated in published studies. As a naturally occurring isoflavone glycoside, it is generally considered to have low toxicity, consistent with the safety profile of other isoflavones found in dietary sources such as soy and lupin. The compound is classified as a research reagent and is not intended for human therapeutic use. Standard laboratory safety precautions should be followed when handling the compound, including the use of appropriate personal protective equipment. Comprehensive toxicological studies, including acute, subchronic, and chronic toxicity assessments, have not been reported.
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| References | |
| Additional Infomation |
Genistein 8-C-glucoside is a C-glycoside compound with a structure in which genistein is replaced at the 8-position by a β-D-glucopyranose residue via a C-glycosidic bond. It is a plant metabolite belonging to the 7-hydroxyisoflavone class and is functionally related to genistein. Genistein 8-C-glucoside has been reported to be found in Dalbergia sissoo, Genista ephedroides, and other organisms with relevant data.
Genistein 8-C-glucoside is a C-glycoside isoflavone naturally occurring in Lupinus luteus L. flowers. It is also known by various synonyms including 8-C-β-Glucosylgenistein, Genistein 8-C-β-D-glucopyranoside, and Genistein 8-C-β-glucoside. The compound is used as a research tool for studying mitochondrial apoptosis pathways and as a reference standard in natural product chemistry. Its C-glycosidic bond provides enhanced stability compared to O-glycosides, making it valuable for mechanistic studies. Not approved for clinical use; intended for research purposes only. |
| Molecular Formula |
C21H20O10
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|---|---|
| Molecular Weight |
432.3775
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| Exact Mass |
432.106
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| CAS # |
66026-80-0
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| PubChem CID |
5281757
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| Appearance |
Off-white to light yellow solid powder
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| Boiling Point |
767.7±60.0 °C at 760 mmHg
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| LogP |
0.091
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
31
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| Complexity |
690
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC(=CC=C1C2=COC3=C(C2=O)C(=CC(=C3[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
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| InChi Key |
HIWJJOYYZFELEZ-FFYOZGDPSA-N
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| InChi Code |
InChI=1S/C21H20O10/c22-6-13-17(27)18(28)19(29)21(31-13)15-12(25)5-11(24)14-16(26)10(7-30-20(14)15)8-1-3-9(23)4-2-8/h1-5,7,13,17-19,21-25,27-29H,6H2/t13-,17-,18+,19-,21+/m1/s1
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| Chemical Name |
5,7-dihydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3128 mL | 11.5639 mL | 23.1278 mL | |
| 5 mM | 0.4626 mL | 2.3128 mL | 4.6256 mL | |
| 10 mM | 0.2313 mL | 1.1564 mL | 2.3128 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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