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| Other Sizes |
| ln Vitro |
3-Hydroxyxanthone inhibited TNF-α induced ICAM-1 expression on HUVECs by 13.7% at a concentration of 66 μg/mL (maximal tolerable concentration).[1]
It inhibited NADPH-catalyzed initiation of liver microsomal lipid peroxidation, reducing the thiobarbituric acid reactive substance (TBRS) to 38% of the control level (i.e., 62% inhibition) at 100 μM.[1] |
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| Enzyme Assay |
Rat liver microsomes were prepared using the method of Ernster and Nordenbrand. The reaction mixture (2.0 mL final volume) contained 0.025 M Tris-HCl (pH 7.5), microsomes (1 mg protein), 3 mM ADP, and 0.15 mM FeCl3. After incubation at 37°C for 10 min, test compound (3-Hydroxyxanthone, 100 μM in 0.2 mL DMSO) was added, followed by another 10 min incubation at 37°C. Then 0.5 mM NADPH was added to initiate enzymatic lipid peroxidation, and the mixture was incubated for different time intervals. The reaction was terminated by adding 0.2 mL of 50% trichloroacetic acid (TCA), 0.2 mL of 5 N HCl, and 1.6 mL of 30% thiobarbituric acid (TBA). Tubes were heated in an oil bath at 95°C for 30 min, cooled, and centrifuged at 3000 rpm. The intensity of the color of the thiobarbituric acid reactive substance (TBRS) was measured at 535 nm. Lipid peroxidation was linear up to 15 min under these conditions.[1]
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| Cell Assay |
Human umbilical vein endothelial cells (HUVECs) were isolated by mild trypsinization and maintained in gelatin-coated flasks in M199 medium supplemented with 20% heat-inactivated fetal calf serum, 2 mM L-glutamine, 100 units/mL penicillin, 100 μg/mL streptomycin, 0.25 μg/mL amphotericin, endothelial cell growth factor (50 μg/mL), and heparin (5 U/mL). Cells were sub-cultured using 0.125% trypsin-0.01 M EDTA in Puck's saline and HEPES buffer, and passages 3-4 were used. Viability was determined by trypan blue exclusion test. For ICAM-1 expression assay, HUVECs plated to confluence in gelatin-coated 96-well plates were incubated with or without 3-Hydroxyxanthone at desired concentrations (66 μg/mL, maximal tolerable concentration) for 1 h, followed by treatment with TNF-α (10 ng/mL) for 16 h. Cells were fixed with 1.0% glutaraldehyde, and non-specific binding was blocked with 3.0% non-fat dry milk in PBS. Cells were incubated overnight at 4°C with ICAM-1 mAb or control IgG Ab (0.25 μg/mL in blocking buffer), then washed with PBS and incubated with peroxidase-conjugated goat anti-mouse secondary antibody (1:1000 in PBS). After washing, cells were exposed to peroxidase substrate (ortho-phenylenediamine dihydrochloride 40 mg/100 mL in citrate phosphate buffer, pH 4.5). The reaction was stopped with 2 N sulfuric acid, and absorbance at 490 nm was measured using an automated microplate reader.[1]
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| Toxicity/Toxicokinetics |
The maximal tolerable concentration of 3-Hydroxyxanthone on HUVECs was determined to be 66 μg/mL using trypan blue exclusion test and morphological observation under microscope. No other toxicity data were reported.[1]
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| References | |
| Additional Infomation |
According to reports, 3-hydroxyxanthon-9-one has been found in Hypericum sampsonii and Rhachidosorus mesosorus, and relevant data are available for reference.
Hydroxy substitution on the xanthone nucleus is required for both antioxidant and ICAM-1 inhibitory activities. Monohydroxylated xanthones like 3-Hydroxyxanthone showed moderate activity, while dihydroxyxanthones exhibited higher potency. The activity is proposed to result from facile oxidation to quinonoid forms. 3-Hydroxyxanthone was less active than 1,4-dihydroxyxanthone (86% ICAM-1 inhibition) and 2,6-dihydroxyxanthone (40.9% inhibition), but more active than methoxylated xanthones (which showed no effect). Acetoxyxanthones showed intermediate activity, possibly due to in situ enzymatic deacetylation.[1] |
| Molecular Formula |
C13H8O3
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|---|---|
| Molecular Weight |
212.2008
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| Exact Mass |
212.047
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| CAS # |
3722-51-8
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| PubChem CID |
5376013
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
403.9±24.0 °C at 760 mmHg
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| Melting Point |
243 °C
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| Flash Point |
162.9±16.4 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.679
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| LogP |
2.83
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
16
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| Complexity |
289
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
XCJHDJAODLKGLG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H8O3/c14-8-5-6-10-12(7-8)16-11-4-2-1-3-9(11)13(10)15/h1-7,14H
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| Chemical Name |
3-hydroxyxanthen-9-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 | 4.7125 mL | 23.5627 mL | 47.1254 mL | |
| 5 mM | 0.9425 mL | 4.7125 mL | 9.4251 mL | |
| 10 mM | 0.4713 mL | 2.3563 mL | 4.7125 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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