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| 5mg |
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Bigelovin is a naturally occuring sesquiterpene lactone isolated from Inula helianthus aquatica, and has been reported to induce apoptosis and show anti-inflammatory and anti-angiogenic activities. It can cause cell cycle arrest and subsequently induce apoptosis in cancer cells. It is formerly known as a potent cytotoxic sesquiterpene lactone from Inula sp. Bigelovin suppresses tumor growth through inducing apoptosis and autophagy via the inhibition of mTOR pathway regulated by ROS generation.
| 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].
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| ln Vivo |
HepG2 xenograft tumor model has anti-activity when bigelovin (BigV, 5, 10, 20 mg/kg) is administered [1].
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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. |
| 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. |
| References | |
| Additional Infomation |
Bigelovin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity. It has a role as an apoptosis inducer, an immunomodulator, an antineoplastic agent and a plant metabolite. It is an acetate ester, an organic heterotricyclic compound, a sesquiterpene lactone, a cyclic ketone and a gamma-lactone.
Bigelovin has been reported in Inula hupehensis, Helenium donianum, and other organisms with data available. |
| 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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