5α-Epoxyalantolactone
5α-Epoxyalantolactone is an orally active, blood-brain barrier-permeable ANXA2 inhibitor. 5α-Epoxyalantolactone binds to ANXA2, blocks the formation of ANXA2-S100A10 heterotetramers, inhibits the membrane trafficking of E-cadherin, and prevents metastasis of breast cancer cells as well as proliferation of breast cancer stem cells. 5α-Epoxyalantolactone improves cognitive and memory impairments by inhibiting the iNOS/COX-2/NF-κB pathway and reducing the activity of cerebral AChE. 5α-Epoxyalantolactone can be used in studies related to Alzheimer's disease and triple-negative breast cancer.
For research use only. We do not sell to patients.
- CAS No.: 65563-75-9
- Formula: C15H20O3
- Molecular Weight:248.32
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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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AnxA2 |
iNOS |
COX-2 |
AChE |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| BV-2 | EC50 |
6.2 μM
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Inhibition of nitric oxide production in LPS-stimulated murine microglial BV-2 cells measured using an NO content assay kit after 24 h incubation.
Inhibition of nitric oxide production in LPS-stimulated murine microglial BV-2 cells measured using an NO content assay kit after 24 h incubation.
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38954263 |
| MDA-MB-231 | IC50 |
16.03 μM
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Antiproliferative activity against human MDA-MB-231 triple-negative breast cancer cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay.
Antiproliferative activity against human MDA-MB-231 triple-negative breast cancer cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay.
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34351142 |
| 4T1 | IC50 |
18.39 μM
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Antiproliferative activity against mouse 4T1 triple-negative breast cancer cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay.
Antiproliferative activity against mouse 4T1 triple-negative breast cancer cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay.
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34351142 |
5α-Epoxyalantolactone (1.25-20 μM; 24 h) does not reduce viability of BV-2 cells[1].
5α-Epoxyalantolactone selectively binds to annexin A2 in MDA-MB-231 triple-negative breast cancer cell lysates in vitro[2].
5α-Epoxyalantolactone (1.25-20 μM; 24 h) potently inhibits NO production in LPS-stimulated BV-2 cells with an EC50 of 6.2 μM, achieving near-basal NO levels at 20 μM[1].
5α-Epoxyalantolactone (1-10 μM; 24 h) dose-dependently inhibits expression of pro-inflammatory proteins iNOS and COX-2 (but not COX-1) in LPS-stimulated BV-2 cells, with maximal inhibition at 10 μM[1].
5α-Epoxyalantolactone (10 μM; 1 h pretreatment) inhibits LPS-induced nuclear translocation of NF-κB p65 in BV-2 cells[1].
5α-Epoxyalantolactone (1-10 μM; 24 h) dose-dependently inhibits production of pro-inflammatory cytokines TNF-α and PGE2 in LPS-stimulated BV-2 cells, with maximal inhibition at 10 μM[1].
5α-Epoxyalantolactone (1-10 μM; 24 h) increases production of the anti-inflammatory cytokine IL-10 in LPS-stimulated BV-2 cells, with a significant effect at 10 μM[1].
5α-Epoxyalantolactone (48 h) inhibits the proliferation of MDA-MB-231 and 4T1 triple-negative breast cancer cells in vitro with IC50 values of 16.03 μM and 18.39 μM, respectively[2].
5α-Epoxyalantolactone (2.5-5.0 μM; 7 days) suppresses the colony-forming ability of MDA-MB-231 and 4T1 triple-negative breast cancer cells in vitro[2].
5α-Epoxyalantolactone (10-20 μM; 96 h) inhibits the proliferation of breast cancer stem cells derived from MDA-MB-231 and 4T1 triple-negative breast cancer cells in vitro[2].
5α-Epoxyalantolactone (2.5-10 μM; 24-36 h) impairs the migratory capability of MDA-MB-231 and 4T1 triple-negative breast cancer cells in vitro[2].
5α-Epoxyalantolactone (2.5-5.0 μM; 24 h) inhibits the invasive capability of MDA-MB-231 and 4T1 triple-negative breast cancer cells in vitro[2].
5α-Epoxyalantolactone (10 μM; 48 h) inhibits the formation of the annexin A2/S100A10 heterotetrameric complex in MDA-MB-468 triple-negative breast cancer cells in vitro[2].
5α-Epoxyalantolactone (5-10 μM; 48 h) reduces membrane-localized E-cadherin and annexin A2 in MDA-MB-468 triple-negative breast cancer cells in vitro[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:murine microglial BV-2 cells
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Concentration:1.25 μM, 2.5 μM, 5 μM, 10 μM, 20 μM
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Incubation Time:24 h
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Result:Showed no cytotoxicity towards BV-2 cells at all tested concentrations, with cell viability remaining near 100% across all groups.
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Cell Line:LPS-stimulated murine microglial BV-2 cells
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Concentration:1 μM, 5 μM, 10 μM
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Incubation Time:24 h
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Result:Dose-dependently suppressed production of TNF-α and PGE2.
Reduced TNF-α levels to 94.77 pg/mL at 10 μM, and PGE2 levels to 194.33 pg/mL at 10 μM.\nSignificantly increased production of the anti-inflammatory cytokine IL-10 at 10 μM, with levels reaching 93.67 pg/mL.
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Cell Line:LPS-stimulated murine microglial BV-2 cells
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Concentration:1 μM, 5 μM, 10 μM
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Incubation Time:24 h
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Result:Dose-dependently inhibited iNOS and COX-2 protein expression, with no effect on COX-1 expression.
Reduced iNOS expression to 0.79 relative to GAPDH at 10 μM, while LPS-treated cells had an iNOS expression level of 1.43 relative to GAPDH.
Reduced COX-2 expression in a dose-dependent manner, with the lowest level observed at 10 μM.
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Cell Line:LPS-stimulated murine microglial BV-2 cells
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Concentration:10 μM
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Incubation Time:1 h pretreatment
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Result:Reduced LPS-induced nuclear translocation of NF-κB p65, as visualized by reduced red fluorescence (NF-κB p65) in cell nuclei (blue DAPI staining) compared to LPS-only treated cells.
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Cell Line:MDA-MB-231, 4T1 triple-negative breast cancer cells
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Concentration:2.5 μM (MDA-MB-231); 5-10 μM (4T1)
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Incubation Time:36 h (MDA-MB-231); 24 h (4T1)
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Result:Reduced the migration distance of MDA-MB-231 cells significantly compared to control, with higher concentrations showing greater inhibition.
Reduced the migration distance of 4T1 cells significantly compared to control, with higher concentrations showing greater inhibition.
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Cell Line:MDA-MB-231, 4T1 triple-negative breast cancer cells
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Concentration:2.5-5.0 μM
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Incubation Time:24 h
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Result:Reduced the number of invading MDA-MB-231 cells significantly compared to control, with the highest concentration showing the greatest reduction.
Reduced the number of invading 4T1 cells significantly compared to control, with the highest concentration showing the greatest reduction.
5α-Epoxyalantolactone (100 mg/kg; p.o.; daily; 36 days) inhibits orthotropic triple-negative breast cancer tumor growth by 30% and reduces lung and liver metastasis in female BALB/c nude mice without affecting bodyweight[2].
5α-Epoxyalantolactone (100 mg/kg; p.o.; daily; 20 days) significantly reduces lung metastatic burden and lung mass in a triple-negative breast cancer tail vein metastasis model in female BALB/c nude mice[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6J (male, 6-8 weeks old, 25-30 g, scopolamine-induced amnesia)[1]
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Dosage:10 mg/kg; 30 mg/kg
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Administration:i.p.; daily; 21 days
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Result:Reduced Barnes maze escape latency to 57.35 s (10 mg/kg) and 38.04 s (30 mg/kg) on day 4 compared to the scopolamine-only group.
Increased Barnes maze time spent in the target quadrant to 39.49 s (10 mg/kg) and 39.98 s (30 mg/kg) on day 5 compared to the scopolamine-only group.
Increased Y-maze spontaneous alternation ratio to 57.42% (10 mg/kg) and 61.55% (30 mg/kg) compared to the scopolamine-only group.
Reduced brain AChE activity to 0.23 U/mg prot (30 mg/kg) compared to the scopolamine-only group.
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Animal Model:BALB/c nude (female, six-week-old, orthotropic triple-negative breast cancer model)[2]
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Dosage:100 mg/kg
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Administration:p.o.; daily; 36 days
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Result:Induced an average tumor growth inhibition (TGI) of about 30%.
Significantly reduced the number of surface-visible lung and liver macrometastases.
Showed smaller macrometastases in lungs and livers compared to controls.
Did not visibly affect average mouse bodyweight.
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Animal Model:BALB/c nude (female, six-week-old, triple-negative breast cancer tail vein metastasis model)[2]
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Dosage:100 mg/kg
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Administration:p.o.; daily; 20 days
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Result:Significantly reduced lung metastatic burden as measured by bioluminescence signaling.
Reduced lung mass compared to vehicle controls.
Showed less lung metastasis compared to controls.
Chemical Information
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CAS No. 65563-75-9
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Molecular Weight 248.32
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Formula C15H20O3
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SMILES
C[C@]12[C@]3([C@H](CCC2)C)[C@@]([C@@]4([H])[C@@](OC(C4=C)=O)([H])C1)([H])O3
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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
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
5α-Epoxyalantolactone Related Classifications
HY-N21980 Related Classifications
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