| Size | Price | Stock | Qty |
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| 1mg |
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| Targets |
Biliatresone induces a decrease in glutathione (GSH) levels and a significant decrease in SOX17 cholangiocyte levels. It causes a reduction in primary cilia and a dose-dependent decrease in visible microtubules, suggesting that it decreases microtubule stability in primary neonatal mouse extrahepatic cholangiocytes.
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| ln Vitro |
Primary cilia can be reduced by bilitresone, and microtubule stability can be observed in a number-dependent manner, suggesting that bilitresone can decrease the microtubule stability of primary newborn extrahepatic bile ducts [1]. In mice, biliatresone (2 μg/mL) causes anomalies in the cholangiocytes and ruptures the spheroid lumen [1].
In primary neonatal mouse extrahepatic cholangiocytes, biliatresone (2 µg/mL) causes a reduction in primary cilia and a dose-dependent decrease in visible microtubules, suggesting decreased microtubule stability. It induces a decrease in glutathione (GSH) levels and significantly reduces SOX17 cholangiocyte levels. |
| ln Vivo |
In zebrafish experiments, the lethal dose of Biliatresone was found to be 1 μg/mL. Biliatresone is toxic at levels between 0.065 and 1.0 μg/mL and is dramatically reduced at higher concentrations [1]. The larvae treated with modest dosages at 5 dpf [0.0625 μg/mL (0.2 μM) and 0.125 μg/mL (0.4 μM)] only displayed severe gallbladder problems, while the larvae treated with the prior group clearly displayed morphological defects related to the gallbladder and extrahepatic ducts [1].
Biliatresone induces C57BL/6J neonatal cholangiopathy, characterized by extrahepatic cholangiocyte damage and fibrosis in mice. It induces a decrease in glutathione (GSH) levels and a significant decrease in SOX17 cholangiocyte levels in vivo. These effects model the pathophysiology of biliary atresia, making it a valuable tool for studying this neonatal liver disease. |
| Enzyme Assay |
In vitro receptor/ enzyme binding assays for biliatresone typically involve incubating the compound with primary neonatal mouse extrahepatic cholangiocytes or isolated cellular components. Microtubule stability is assessed using immunofluorescence microscopy to visualize microtubule networks and primary cilia. Glutathione levels are measured using colorimetric or fluorometric GSH assay kits. SOX17 expression is evaluated by immunostaining or Western blot.
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| Cell Assay |
Cell-based assays for biliatresone are conducted using primary neonatal mouse extrahepatic cholangiocytes cultured in specialized media. Cells are treated with biliatresone at concentrations ranging from 0.5-5 µg/mL for 24-72 hours. Microtubule stability is assessed by immunofluorescence microscopy. Glutathione levels are measured using commercial assay kits. SOX17 expression is evaluated by immunostaining or quantitative PCR.
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| Animal Protocol |
In vivo experiments involve administering biliatresone to neonatal C57BL/6J mice, typically via intraperitoneal injection. Treated animals are evaluated for cholangiopathy, including extrahepatic cholangiocyte damage and fibrosis. Glutathione levels and SOX17 expression are measured in liver and bile duct tissues. Bile duct morphology and primary cilia are examined by histology and electron microscopy.
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| ADME/Pharmacokinetics |
No detailed pharmacokinetic data are specifically available for biliatresone. As a naturally occurring isoflavonoid toxin (molecular weight ~280-300), it is expected to have moderate bioavailability. Further PK studies including absorption, distribution, metabolism, and excretion are needed to fully characterize its in vivo behavior.
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| Toxicity/Toxicokinetics |
No comprehensive toxicology data are specifically available for biliatresone. The compound induces cholangiopathy in neonatal mice, characterized by extrahepatic cholangiocyte damage and fibrosis. It decreases glutathione levels and reduces SOX17 expression. These effects model biliary atresia pathogenesis. Proper laboratory safety precautions should be followed when handling this compound.
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| References |
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| Additional Infomation |
Biliatresone belong to the benzodioxane class of compounds, with the structure 1,3-benzodioxane, substituted at position 5 with a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group, and substituted at positions 4 and 6 with methoxy groups. It is a very rare isoflavone compound, belonging to the 1,2-diaryl-2-propenone class, and is found in Dysphania glomulifera and D. littoralis. Its enone moiety is highly reactive, readily undergoing Michael addition reactions with water and methanol. In zebrafish models, Biliatresone have been shown to cause extrahepatic biliary atresia (occlusion or interruption of the extrahepatic biliary system, leading to obstruction of bile outflow). It is both a toxin and a plant metabolite. It belongs to the benzodioxane class, enone class, aromatic ketone class, aromatic ether class, and phenolic class.
Biliatresone is a naturally occurring 1,2-diaryl-2-propenone class isoflavonoid toxin isolated from Dysphania glomulifera and D. littoralis. It induces biliary atresia-like pathology in neonatal mice, providing a unique model for studying this severe neonatal liver disease. Its mechanism involves GSH depletion, SOX17 downregulation, and microtubule destabilization. |
| Molecular Formula |
C18H16O6
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|---|---|
| Molecular Weight |
328.316045761108
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| Exact Mass |
328.094
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| Elemental Analysis |
C, 65.85; H, 4.91; O, 29.24
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| CAS # |
1801433-90-8
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| PubChem CID |
124079379
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| Appearance |
White to yellow viscous liquid
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| LogP |
3.2
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
24
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| Complexity |
478
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1COC2=CC(=C(C(C(=C)C3C=CC=CC=3O)=O)C(=C12)OC)OC
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| InChi Key |
SIKIIXNKUAAGAM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H16O6/c1-10(11-6-4-5-7-12(11)19)16(20)15-13(21-2)8-14-17(18(15)22-3)24-9-23-14/h4-8,19H,1,9H2,2-3H3
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| Chemical Name |
1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one
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| Synonyms |
biliatresone; CHEBI:131631; RefChem:119806; 1801433-90-8; 1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-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) |
DMSO : ~50 mg/mL (~152.3 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2 mg/mL (6.09 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 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 mg/mL (6.09 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 20.0 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. View More
Solubility in Formulation 3: ≥ 2 mg/mL (6.09 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0458 mL | 15.2290 mL | 30.4581 mL | |
| 5 mM | 0.6092 mL | 3.0458 mL | 6.0916 mL | |
| 10 mM | 0.3046 mL | 1.5229 mL | 3.0458 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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