Beauvericin
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Beauvericin is a cyclohexapeptide Fusarium toxin with insecticidal, antibacterial, anticancer, antiviral and cytotoxic activities. Beauvericin causes cellular genotoxicity by producing DNA breaks, chromosomal aberrations and micronuclei, and inhibits the PI3K/AKT pathway to induce apoptosis, thereby inhibiting the growth of HCC. In addition, Beauvericin affects immune function by inhibiting lymphocyte proliferation and interfering with the differentiation process of human monocytes into macrophages.
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- Purity: 99.97%
- CAS No.: 26048-05-5
- 화학식: C45H57N3O9
- 분자량:783.95
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보관:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
Biological Activity
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ACAT |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HepG2 | IC50 |
1 μM
Compound: 12
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Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay
Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay
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[PMID: 36288556] |
| Huh-7 | IC50 |
4.3 μM
Compound: 12
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Antiproliferative activity against human Huh-7 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay
Antiproliferative activity against human Huh-7 cells assessed as reduction in cell viability after 48 hr by CCK-8 assay
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[PMID: 36288556] |
Beauvericin (0-20 μM; 12, 24 and 36 h) has a strong antiproliferative activity against H22 hepatoma cells and promotes apoptosis of H22 hepatoma cells[5]. Beauvericin (50 μM; 72 h) induces apoptosis in turkey peripheral mononuclear cells[6]. Beauvericin (0.3-100 µM) reversibly inhibits L-type voltage-dependent Ca2+ current (ICa,L) in NG108-15 neuronal cells in a concentration-dependent manner with an IC50 value of 4 µM[7]. Beauvericin has IC50 values of 1.0 µM, 2.9 µM, and 2.5 µM for immature dendritic cells, mature dendritic cells, and macrophages, respectively[8]. Beauvericin (1.6 and 2.4 µM; 2 d) reduces CCR7 expression and increases IL-10 secretion in maturing dendritic cells[8]. Beauvericin is a potent inhibitor of CYP3A1/2 in rat liver microsomes (IC50=1.3 mM)[9].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:H22 liver cancer cells
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Concentration:0, 1, 3, 5,10,15 and 20 µM
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Incubation Time:12、24 and 36 h
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Result:Inhibited the growth of H22 cells in a dose-dependent manner.
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Cell Line:H22 liver cancer cells
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Concentration:0, 1, 3, 5,10,15 and 20 µM
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Incubation Time:12、24 and 36 h
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Result:Upregulated the Bax/Bcl-2 ratio and the levels of cleaved caspase-9 and cleaved caspase-3, and downregulated the p-PI3K/PI3K ratio and p-AKT/AKT ratio.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:BALB/c mice injected subcutaneously with mouse CT-26 colon cancer cells on the right side[3]
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Dosage:5 mg/kg
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Administration:ntraperitoneal injection (i.p.);The drug was administered on the third day after the injection of colon cancer cells and continued once a day for five days, then stopped for two days of observation, and continued on the tenth day after the injection of colon cancer cells, and continued once a day for four days.
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Result:Reduced the average tumor volume by 52.8 % and the average tumor weight by 60 %.
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Animal Model:Human cervical cancer KB-3-1 xenograft mouse model[3]
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Dosage:5 mg/kg
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Administration:Intraperitoneal injection (i.p.); The drug was administered once a day starting on the fifth day after cervical cancer injection for five days, followed by two days of observation. The drug was administered once a day starting on the twelfth day after cervical cancer cell injection for four days.
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Result:Reduced the average tumor volume by 31.3 % and the average tumor weight by 31.2 %.
Chemical Information
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CAS No. 26048-05-5
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Appearance Solid
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분자량 783.95
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화학식 C45H57N3O9
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Color White to off-white
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SMILES
CN([C@H](C(O[C@](C(N([C@H](C(O[C@@H]1C(C)C)=O)CC2=CC=CC=C2)C)=O)([H])C(C)C)=O)CC3=CC=CC=C3)C([C@H](OC([C@@H](N(C1=O)C)CC4=CC=CC=C4)=O)C(C)C)=O
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Structure Classification
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Initial Source
Fusarium proliferatum,F. semitectum, and F. subglutinans
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선적
Room temperature in continental US; may vary elsewhere.
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보관
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
용액&용해도
DMSO : 100 mg/mL (127.56 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
순도&문서
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Data Sheet (287 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Mallebrera B, et al. In vitro mechanisms of Beauvericin toxicity: A review[J]. Food and Chemical Toxicology, 2018, 111: 537-545. [Content Brief]
[2]. Wang Q, et al. Beauvericin, a bioactive compound produced by fungi: a short review[J]. Molecules, 2012, 17(3): 2367-2377. [Content Brief]
[3]. Heilos D, et al. The natural fungal metabolite beauvericin exerts anticancer activity in vivo: a pre-clinical pilot study[J]. Toxins, 2017, 9(9): 258. [Content Brief]
[5]. Wang G, et al. Beauvericin exerts an anti-tumor effect on hepatocellular carcinoma by inducing PI3K/AKT-mediated apoptosis[J]. Archives of Biochemistry and Biophysics, 2023, 745: 109720. [Content Brief]
[6]. Dombrink-Kurtzman M A. Fumonisin and beauvericin induce apoptosis in turkey peripheral blood lymphocytes[J]. Mycopathologia, 2003, 156: 357-364. [Content Brief]
[7]. Wu S N, et al. Block of L-type Ca2+ current by beauvericin, a toxic cyclopeptide, in the NG108-15 neuronal cell line[J]. Chemical research in toxicology, 2002, 15(6): 854-860. [Content Brief]
[8]. Ficheux A S, et al. Effects of beauvericin, enniatin b and moniliformin on human dendritic cells and macrophages: An in vitro study[J]. Toxicon, 2013, 71: 1-10. [Content Brief]
[9]. Mei L, et al. An inhibition study of beauvericin on human and rat cytochrome P450 enzymes and its pharmacokinetics in rats[J]. Journal of enzyme inhibition and medicinal chemistry, 2009, 24(3): 753-762. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.2756 mL | 6.3780 mL | 12.7559 mL | 31.8898 mL |
| 5 mM | 0.2551 mL | 1.2756 mL | 2.5512 mL | 6.3780 mL | |
| 10 mM | 0.1276 mL | 0.6378 mL | 1.2756 mL | 3.1890 mL | |
| 15 mM | 0.0850 mL | 0.4252 mL | 0.8504 mL | 2.1260 mL | |
| 20 mM | 0.0638 mL | 0.3189 mL | 0.6378 mL | 1.5945 mL | |
| 25 mM | 0.0510 mL | 0.2551 mL | 0.5102 mL | 1.2756 mL | |
| 30 mM | 0.0425 mL | 0.2126 mL | 0.4252 mL | 1.0630 mL | |
| 40 mM | 0.0319 mL | 0.1594 mL | 0.3189 mL | 0.7972 mL | |
| 50 mM | 0.0255 mL | 0.1276 mL | 0.2551 mL | 0.6378 mL | |
| 60 mM | 0.0213 mL | 0.1063 mL | 0.2126 mL | 0.5315 mL | |
| 80 mM | 0.0159 mL | 0.0797 mL | 0.1594 mL | 0.3986 mL | |
| 100 mM | 0.0128 mL | 0.0638 mL | 0.1276 mL | 0.3189 mL |