| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Inhibits serotonin (5-HT) uptake in rat brain synaptosomes (IC50 = 4.7 ± 0.3 μM) [2]
No or very slight (<10%) inhibitory effect on ligand binding to 5-HT1B receptors in rat striatum and hippocampus [2] |
|---|---|
| ln Vitro |
Inhibits the accumulation of [3H]5-HT in crude synaptosomal suspensions prepared from rat brain frontal cortex in a concentration-dependent manner. The IC50 value for serotonin uptake inhibition is 4.7 ± 0.3 μM [2]
Shows no or very slight (<10%) inhibitory effect on specific binding of [3H]5-HT to 5-HT1B receptors in rat striatum and hippocampus at concentrations ranging from 10^-9 to 10^-4 M [2] |
| Enzyme Assay |
Synaptosomal uptake assay: Crude synaptosomal fraction from rat brain frontal cortex is preincubated for 5 min at 37°C in a solution containing 62.5 nM [3H]5-HT in Krebs-Henseleit bicarbonate buffer (pH 7.4) with increasing concentrations (10^-4 to 10^-9 M) of the test compound. Non-specific accumulation is observed at 0°C in the presence of 1 μM fluoxetine. The reaction is stopped by adding ice-cold incubation buffer and immediate centrifugation (7000 x g, 10 min, 4°C). The pellet is washed and dissolved in solubilizer (Triton X100 + 50% ethanol, 1:4). Radioactivity is counted in liquid scintillation cocktail. GBR 12783 (30 nM) is added to block serotonin transporters operated by dopamine nerve terminals. IC50 values are calculated from log-probit analyses [2]
5-HT1B receptor binding assay: Crude membrane preparations from rat striatum (or hippocampus) are homogenized in 0.05 M Tris buffer (pH 7.7) and centrifuged at 48,000 x g for 10 min. The pellet is resuspended, incubated at 37°C for 10 min, and recentrifuged. The final pellet is resuspended in 0.05 M Tris buffer containing 4 mM CaCl2, 0.01% ascorbic acid, and 10 mM pargyline. Assays are performed with membrane preparation, buffer, vehicle/drug, [3H]5-HT (nM), and 1 μM spiroperidol. Tubes are incubated for 15 min at 25°C. The assay is stopped by vacuum filtration through filters, which are washed with ice-cold Tris buffer. Filters are counted in scintillation cocktail. Specific binding is defined as the difference between total binding and binding in the presence of 10 μM 5-HT [2] |
| Animal Protocol |
Male Wistar rats (180-200 g) are used. Animals are housed in cages (4 per cage) with free access to water and food in a well-ventilated room at 21°C ± 1°C under a 12h light-dark cycle. For synaptosomal uptake and binding experiments, rats are sacrificed by decapitation, and brains are rapidly removed. The frontal cortex is dissected for synaptosomal uptake assays; the striatum and hippocampus are dissected for 5-HT1B binding assays [2]
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| References | |
| Additional Infomation |
Gentisein is a xanthone compound with the structure 9H-xanthone-9-one, substituted with hydroxyl groups at positions 1, 3, and 7. It is a plant metabolite belonging to the xanthone and polyphenol classes. Gentisein has been reported in Anaxagorea luzonensis, Hypericum henryi, and other organisms with relevant data.
Gentisein is a xanthone derivative isolated from Hypericum annulatum Moris subsp. annulatum (a perennial herb indigenous to the Balkan Peninsula and Sardinia). It is obtained as yellow needles following acid hydrolysis of hypericophenonoside (2'-O-β-D-glucopyranosyl-2,4,5',6-tetrahydroxybenzophenone) [2] Previous studies have shown that benzophenones isolated from Hypericum annulatum exert antioxidant and cytotoxic protective effects in different experimental systems. Gentisein has been studied for its potential antidepressant-like mechanisms [2] The mechanism of action of Gentisein is probably not associated with specific binding to serotonin receptors but may be related to the inhibition of serotonin uptake, which differs from classical antidepressants that directly interact with monoaminergic transmission via MAOI, transporter blockade, or receptor stimulation [2] |
| Molecular Formula |
C13H8O5
|
|---|---|
| Molecular Weight |
244.202
|
| Exact Mass |
244.037
|
| CAS # |
529-49-7
|
| PubChem CID |
5281635
|
| Appearance |
Light yellow to yellow solid powder
|
| Melting Point |
321 - 323 °C
|
| LogP |
2.063
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
18
|
| Complexity |
344
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
JJUNZBRHHGLJQW-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C13H8O5/c14-6-1-2-10-8(3-6)13(17)12-9(16)4-7(15)5-11(12)18-10/h1-5,14-16H
|
| Chemical Name |
Xanthen-9-one, 1,3,7-trihydroxy-
|
| Synonyms |
NSC-329491 NSC329491Gentisein NSC 329491
|
| 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~409.50 mM)
|
|---|---|
| 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 | 4.0950 mL | 20.4750 mL | 40.9500 mL | |
| 5 mM | 0.8190 mL | 4.0950 mL | 8.1900 mL | |
| 10 mM | 0.4095 mL | 2.0475 mL | 4.0950 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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