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| Targets |
Bigelovin targets retinoid X receptor α (RXRα), functioning as a selective agonist. By activating RXRα, bigelovin modulates gene expression and cellular signaling pathways. The compound induces apoptosis and autophagy through the inhibition of the mTOR pathway regulated by ROS generation. Its antitumor effects are mediated through the induction of cell death and the suppression of tumor growth. The compound's selectivity for RXRα makes it a valuable tool for studying RXRα signaling.
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| ln Vitro |
Bigelovin (0–20 μM, 24-72 h) promotes autophagy and death and dramatically reduces the viability of translocated cells [1]. Beclin-1, p62, LC3B-II, and p62 levels are all markedly increased by bigelovin, with a matching downward trend. Bigelovin inhibits mTOR dye, which is controlled by the generation of ROS, and causes cell death [1].
In vitro, bigelovin significantly inhibits cell viability of liver cancer cells and induces apoptosis and autophagy at concentrations of 0-20 µM for 24-72 hours. It suppresses tumor growth through inducing apoptosis and autophagy via the inhibition of the mTOR pathway regulated by ROS generation. Bigelovin is a selective RXRα agonist and a potent cytotoxic sesquiterpene lactone. In cell-based assays, bigelovin treatment results in reduced cell viability, increased apoptosis, and activation of autophagy pathways. |
| ln Vivo |
HepG2 xenograft tumor model has anti-activity when bigelovin (BigV, 5, 10, 20 mg/kg) is administered [1].
In vivo, bigelovin has been shown to suppress tumor growth in animal models. Its antitumor effects are mediated through the induction of apoptosis and autophagy via the inhibition of the mTOR pathway regulated by ROS generation. The compound's efficacy has been demonstrated in preclinical studies. Comprehensive in vivo studies are needed to fully characterize its pharmacokinetic and pharmacodynamic profiles. Bigelovin is a promising lead compound for the development of anticancer therapies. |
| Enzyme Assay |
In vitro receptor binding assays for bigelovin involve measuring its binding affinity to retinoid X receptor α (RXRα). The receptor is incubated with a radiolabeled ligand and varying concentrations of bigelovin. The displacement of the radiolabeled ligand is measured, and the IC₅₀ or Ki value is calculated. The compound's functional activity as an RXRα agonist is assessed using reporter gene assays or by measuring the expression of RXRα target genes. These assays confirm the compound's mechanism of action.
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| Cell Assay |
Cell viability assay [1]
Cell Types: HepG2 and SMMC-7721 cells. Tested Concentrations: 0-20 μM. Incubation Duration: 24, 48, 72 hrs (hours). Experimental Results: Cell viability of HepG2 and SMMC-7721 cells was Dramatically diminished in a dose- and time-dependent manner. No significant differences were observed in the cell viability of normal liver cell lines LO2 and LX2 after 24, 48 or 72 hrs (hours) of BigV treatment. Western Blot Analysis[1] Cell Types: HepG2 and SMMC-7721 cells. Tested Concentrations: 0-10μM. Incubation Duration: 24 hrs (hours). Experimental Results: After BigV treatment, the expression of Bcl-2 diminished, while the expression of Bax increased. Furthermore, Caspase-9, -3 and PARP cleavage were Dramatically activated after BigV treatment. In vitro cell-based assays for bigelovin evaluate its effects on cancer cell viability, apoptosis, and autophagy. Cancer cells are cultured in appropriate media and treated with serial dilutions of bigelovin (0-20 µM) for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. Apoptosis is quantified by measuring caspase-3/7 activity or by Annexin V staining. Autophagy is assessed by measuring LC3-II accumulation or by using fluorescent autophagy reporters. ROS generation is measured using fluorescent probes. These assays confirm the compound's antitumor activity. |
| Animal Protocol |
Animal/Disease Models: HepG2 xenograft model based on male athymic BALB/c nude mice (5-6 weeks old), 18-22 g) [1].
Doses: 5, 10, 20 mg/kg. Doses: intravenously (iv) (iv)(iv) every 2 days. Experimental Results: The tumor growth rate in the BigV treatment group was Dramatically slowed down in a dose-dependent manner, and the tumor weight was also diminished. No significant changes in body weight and serum liver enzyme levels (AST, ALT and LDH) were observed after BigV administration. Western blot results of tumor tissue demonstrated activation of apoptosis and autophagy, characterized by increased levels of cleaved Caspase-3 and PARP, as well as LC3BII. mTOR inactivation was also observed in tumor tissues isolated from BigV-treated mice. In vivo animal experiments for bigelovin have been conducted in mouse xenograft models of cancer. Tumor-bearing mice are treated with bigelovin via various routes of administration. Tumor growth is monitored by caliper measurements, and tumor growth inhibition is calculated. Apoptosis and autophagy in tumor tissues are assessed by immunohistochemistry or Western blot. Pharmacokinetic studies are conducted to determine the compound's half-life, clearance, and tissue distribution. Comprehensive in vivo studies are ongoing. |
| ADME/Pharmacokinetics |
Pharmacokinetic (PK) data for bigelovin are limited. The compound has a molecular weight of 304.34 g/mol and is a sesquiterpene lactone. It is soluble in organic solvents such as DMSO. The compound's metabolic stability, half-life, and bioavailability have not been fully characterized. Comprehensive ADME studies are needed to fully characterize the pharmacokinetic profile of bigelovin.
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| Toxicity/Toxicokinetics |
The toxicity profile of bigelovin has not been extensively characterized. As a potent cytotoxic sesquiterpene lactone, the compound may have off-target effects on normal cells. In laboratory settings, bigelovin should be handled as a hazardous chemical. Appropriate personal protective equipment should be used when handling the compound. The compound is for research use only and is not intended for human or veterinary use. Comprehensive toxicological studies are needed.
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| References | |
| Additional Infomation |
Bigelovin is a sesquiterpene lactone with the structure 3,3a,4,4a,7a,8,9,9a-octahydroazolo[6,5-b]furan-2,5-dione, substituted with methyl groups at positions 4a and 8, a methylene group at position 3, and an acetoxy group at position 4. It was isolated from Inula hupehensis and possesses antitumor activity. Bigelovin can function as an apoptosis inducer, immunomodulator, antitumor agent, and plant metabolite. It is an acetate, an organic heterocyclic tricyclic compound, a sesquiterpene lactone, a cyclic ketone, and a γ-lactone. Bigelovin has been reported to be found in Inula hupehensis, Helenium donianum, and other organisms with relevant data.
Bigelovin is a sesquiterpene lactone isolated from Inula hupehensis that functions as a selective agonist of retinoid X receptor α (RXRα). It has a molecular formula of C₁₇H₂₀O₅ and a molecular weight of 304.34 g/mol. Bigelovin exhibits antitumor effects through the induction of apoptosis and autophagy. It suppresses tumor growth through the inhibition of the mTOR pathway regulated by ROS generation. Bigelovin is a promising lead compound for anticancer drug development. |
| Molecular Formula |
C17H20O5
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|---|---|
| Molecular Weight |
304.342
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| Exact Mass |
304.131
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| CAS # |
3668-14-2
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| PubChem CID |
3080597
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| Appearance |
White to off-white solid powder
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| LogP |
1.817
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
22
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| Complexity |
604
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C[C@@H]1C[C@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)OC(=O)C)C(=C)C(=O)O2
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| InChi Key |
DCNRYQODUSSOKC-MMLVVLEOSA-N
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| InChi Code |
InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1
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| Chemical Name |
[(3aS,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
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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 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~328.58 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.21 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 25.0 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: ≥ 2.5 mg/mL (8.21 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 25.0 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: ≥ 2.5 mg/mL (8.21 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 | 3.2858 mL | 16.4290 mL | 32.8580 mL | |
| 5 mM | 0.6572 mL | 3.2858 mL | 6.5716 mL | |
| 10 mM | 0.3286 mL | 1.6429 mL | 3.2858 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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