2-Methoxyjuglone
2-Methoxyjuglone, a naphthoquinone, is an apoptosis inducer. 2-Methoxyjuglone activates caspase-9 and caspase-3 via the mitochondrial cytochrome c-dependent intrinsic apoptosis cascade. 2-Methoxyjuglone increases pro-apoptotic Bax levels, decreases anti-apoptotic Bcl-2 levels, and promotes mitochondrial cytochrome c release. 2-Methoxyjuglone induces apoptosis morphological features, early apoptosis, S-phase and G2/M-phase cell cycle arrest, and DNA double-strand breaks. 2-Methoxyjuglone exerts activity against Gram-positive bacteria, pathogenic fungi, and phytopathogenic fungi. 2-Methoxyjuglone can be used for the research of hepatocellular carcinoma, osteosarcoma, colon adenocarcinoma, breast cancer, fungal infection, bacterial infection.
For research use only. We do not sell to patients.
- CAS No.: 15127-94-3
- Formula: C11H8O4
- Molecular Weight:204.18
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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Caspase 3 |
Caspase 9 |
Bax |
Bcl-2 |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| A549 | IC50 |
0.08 μg/mL
Compound: 4
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Cytotoxicity against human A549 cells by MTT assay
Cytotoxicity against human A549 cells by MTT assay
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[PMID: 9599266] |
2-Methoxyjuglone (1.6-8.0 μg/mL; 24, 48, 72 h) reduces HepG2 human hepatocellular carcinoma cell viability in a dose- and time-dependent manner, with IC50 values of 3.8, 3.7, and 2.7 μg/mL after 24, 48, and 72 h of treatment, respectively[1].
2-Methoxyjuglone (4.8-8.0 μg/mL; 24 h) induces apoptotic morphological changes (cell shrinkage, membrane blebbing) in HepG2 human hepatocellular carcinoma cells[1].
2-Methoxyjuglone (1.6-8.0 μg/mL; 24, 48 h) induces S phase cell cycle arrest in HepG2 human hepatocellular carcinoma cells after 24 and 48 h of treatment at 1.6-8.0 μg/mL, and causes DNA fragmentation (sub-G1 phase accumulation) at 6.4 and 8.0 μg/mL after 48 h[1].
2-Methoxyjuglone (1.6-4.8 μg/mL; 24 h) induces HepG2 human hepatocellular carcinoma cell apoptosis via the mitochondrial cytochrome c-dependent intrinsic pathway, with dose-dependent increases in cytochrome c release, caspase-9 and caspase-3 activation, PARP cleavage, and Bax/Bcl-2 ratio after 24 h of treatment at 1.6-4.8 μg/mL[1].
2-Methoxyjuglone (10 μM; 1.25 μM, 24 h) potently inhibits DNA topoisomerase II at 10 μM and induces DNA double-strand breaks in human osteosarcoma U2OS cells at 1.25 μM, contributing to its cytotoxic activity[2].
2-Methoxyjuglone (62.5 μg/mL; 100 μM) exhibits potent in vitro antibacterial activity against multiple Gram-positive bacterial strains, with 100% growth inhibition of Bacillus subtilis at 100 μM, strong activity against Bacillus subtilis at 62.5 μg/mL[2].
2-Methoxyjuglone (0.25%-4%; 250 μg/mL; 8 μg/mL; 0.1-0.5 mg/mL) exhibits broad-spectrum in vitro antifungal activity against pathogenic and phytopathogenic fungi, with 100% inhibition of Fusarium graminearum spore germination at 0.5 mg/mL[2].
2-Methoxyjuglone potently inhibits the viability of human colon carcinoma HT-29 cells (IC50 = 2.6 μg/mL) and human breast carcinoma MCF-7 cells (IC50 = 1.2 μg/mL)[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HepG2 human hepatocellular carcinoma cells
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Concentration:1.6, 3.2, 4.8, 6.4, 8.0 μg/mL
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Incubation Time:24, 48, 72 h
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Result:Induced dose-dependent and time-dependent decreases in cell viability.
Reached IC50 values of 3.8 μg/mL (24 h), 3.7 μg/mL (48 h), and 2.7 μg/mL (72 h).
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Cell Line:HepG2 human hepatocellular carcinoma cells
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Concentration:4.8, 8.0 μg/mL
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Incubation Time:24 h
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Result:Caused cell shrinkage and membrane blebbing at 4.8 μg/mL.
Induced almost all cells to shrink with no normal morphological features at 8.0 μg/mL.\nReduced the number of cells on coverslips significantly and induced nuclear condensation with yellow staining (early apoptosis) at 4.8 μg/mL.
Caused almost all cells to detach from coverslips, with orange staining and apoptotic body formation (late apoptosis) at 8.0 μg/mL.
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Cell Line:HepG2 human hepatocellular carcinoma cells
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Concentration:1.6, 3.2, 4.8, 6.4, 8.0 μg/mL
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Incubation Time:24, 48 h
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Result:Increased the fraction of cells in the S phase (62%, 64%, 62%, 61%, 59% at 1.6, 3.2, 4.8, 6.4, 8.0 μg/mL, respectively) and decreased fractions in G1 and G2/M phases after 24 h.
Increased the fraction of cells in the S phase (49%, 64%, 66%, 52%, 46% at 1.6, 3.2, 4.8, 6.4, 8.0 μg/mL, respectively) after 48 h.
Induced dramatic increases in sub-G1 phase fraction (18% and 33%, respectively) at 6.4 and 8.0 μg/mL for 48 h, indicating DNA fragmentation associated with apoptosis.
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Cell Line:HepG2 human hepatocellular carcinoma cells
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Concentration:1.6, 3.2, 4.8 μg/mL
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Incubation Time:24 h
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Result:Increased cytoplasmic cytochrome c levels in a dose-dependent manner.
Activated caspase-9 via proteolytic cleavage of the 47 kDa pro-enzyme to the 35 kDa active form, increasing the cleaved/uncleaved ratio.
Activated caspase-3 via proteolytic cleavage of the 35 kDa pro-enzyme to the 17 kDa active form, increasing the cleaved/uncleaved ratio.
Increased the cleaved/uncleaved PARP ratio.
Elevated pro-apoptotic Bax protein levels and reduced anti-apoptotic Bcl-2 protein levels in a dose-dependent manner, resulting in an elevated Bax/Bcl-2 ratio.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Kunming mice (male, SPF, 6 weeks old, 18-22 g, subcutaneous inoculation of H22 hepatocellular carcinoma cells)[1]
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Dosage:0.25 mg/kg; 0.5 mg/kg; 1.0 mg/kg
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Administration:i.p.; daily; 8 days
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Result:Reduced tumor mass in mice.
Did not reduce the normal weight (total weight minus tumor weight) of mice at any tested dose.
Chemical Information
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CAS No. 15127-94-3
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Molecular Weight 204.18
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Formula C11H8O4
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SMILES
O=C1C=C(C(C2=C1C(O)=CC=C2)=O)OC
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Yu HY, et al. 2-methoxyjuglone induces apoptosis in HepG2 human hepatocellular carcinoma cells and exhibits in vivo antitumor activity in a H22 mouse hepatocellular carcinoma model. J Nat Prod. 2013;76(5):889-895. [Content Brief]
[2]. Yu HY, et al. 2-Methoxyjuglone, a Promising Bioactive Compound for Pharmaceutical and Agricultural Purposes: A Review. Curr Med Sci. 2022;42(5):905-912. [Content Brief]
[3]. Li G, et al. DNA topoisomerases I and II inhibitory activity of constituents isolated from Juglans mandshurica. Arch Pharm Res. 2003;26(6):466-470. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
2-Methoxyjuglone Related Classifications
HY-N17440 Related Classifications
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