Vinburnine phosphate
Vinburnine ((-)-Eburnamonine; (-)-Vincamone) phosphate is an orally active, blood-brain barrier permeable immunomodulator and apoptosis inducer. Vinburnine phosphate drives the secretion of IL-24 by activating the P38/MAPK/ATF3 signaling axis. Vinburnine phosphate induces reactive oxygen species production and DNA damage in cancer cells, thereby inhibiting cancer cell proliferation, activating the apoptotic cascade, and enhancing CD8+ T cell function to remodel the tumor immune microenvironment. Vinburnine phosphate can be used in the research of diseases such as melanoma.
For research use only. We do not sell to patients.
- CAS No.: 94134-60-8
- Formula: C19H25N2O5P
- Molecular Weight:392.39
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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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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| SK-MEL-5 | IC50 |
5 μM
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Reduction of cell viability against human melanoma SK-MEL-5 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
Reduction of cell viability against human melanoma SK-MEL-5 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
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40866941 |
| SK-MEL-28 | IC50 |
5 μM
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Reduction of cell viability against human melanoma SK-MEL-28 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
Reduction of cell viability against human melanoma SK-MEL-28 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
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40866941 |
| A-375 | IC50 |
5 μM
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Reduction of cell viability against human melanoma A375 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
Reduction of cell viability against human melanoma A375 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
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40866941 |
| B16-F10 | IC50 |
7.5 μM
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Reduction of cell viability against murine melanoma B16F10 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
Reduction of cell viability against murine melanoma B16F10 cells assessed by CCK-8 assay after exposure for 24 h, 48 h, or 72 h.
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40866941 |
Vinburnine phosphate (2.5-20 μM; 24-72 h) dose- and time-dependently reduces viability of SK-MEL-5, SK-MEL-28, A375, and B16F10 melanoma cells with IC50 values of ~5 μM (human lines) and ~7.5 μM (murine line), while sparing normal human melanocytes[1].
Vinburnine phosphate (2.5-10 μM; 48 h) dose-dependently suppresses colony formation in SK-MEL-5, SK-MEL-28, A375, and B16F10 melanoma cells, with near-complete inhibition at 5 μM in human lines and significant inhibition at 10 μM in the murine line[1].
Vinburnine phosphate inhibits migration of A375, SK-MEL-28, and SK-MEL-5 melanoma cells in a wound healing assay[1].
Vinburnine phosphate (2.5-5 μM; 12-24 h) inhibits migration and invasion of A375, SK-MEL-28, and SK-MEL-5 melanoma cells in Transwell assays[1].
Vinburnine phosphate induces ROS overproduction in A375, SK-MEL-28, and SK-MEL-5 melanoma cells, which mediates its growth-inhibitory effects[1].
Vinburnine phosphate induces DNA strand breaks in A375, SK-MEL-28, and SK-MEL-5 melanoma cells[1].
Vinburnine phosphate activates the DNA damage response pathway in A375, SK-MEL-28, SK-MEL-5, and B16F10 melanoma cells, as evidenced by upregulated p-ATM, p-ATR, and γH2AX detected via Western blot[1].
Vinburnine phosphate (2.5-5 μM; 24 h) induces G0/G1 phase cell cycle arrest in A375, SK-MEL-28, and SK-MEL-5 melanoma cells[1].
Vinburnine phosphate (2.5-5 μM; 24 h) induces apoptosis in A375, SK-MEL-28, and SK-MEL-5 melanoma cells as measured by flow cytometry[1].
Vinburnine phosphate (2.5-5 μM; 24 h) modulates apoptosis-related protein expression in A375, SK-MEL-28, and SK-MEL-5 melanoma cells via upregulation of pro-apoptotic proteins and downregulation of anti-apoptotic BCL-2[1].
Vinburnine phosphate activates the IL-24 promoter to enhance its transcriptional activity in melanoma cells[1].
Vinburnine phosphate (2.5-5 μM; 48 h) enhances the interaction between ATF3 protein and the IL-24 promoter in SK-MEL-28 melanoma cells[1].
Vinburnine phosphate enhances the in vitro cytotoxicity of PBMCs and CD8+ T cells against A375-luciferase and B16F10-luciferase melanoma cells[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:SK-MEL-5, SK-MEL-28, A375, B16F10, PIG1
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Concentration:2.5-20 μM
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Incubation Time:24-72 h
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Result:Significantly reduced cell viability in a dose- and time-dependent manner across all tested melanoma cell lines.
Exhibited IC50 values of approximately 5 μM for SK-MEL-5, SK-MEL-28, and A375 cells, and around 7.5 μM for B16F10 cells.
Showed no cytotoxic effect in normal human melanocytes (PIG1) even at 20 μM.
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Cell Line:A375, SK-MEL-28, SK-MEL-5
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Concentration:2.5-5 μM
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Incubation Time:24 h
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Result:Markedly arrested melanoma cells in the G0/G1 phase.
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Cell Line:A375, SK-MEL-28, SK-MEL-5
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Concentration:2.5-5 μM
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Incubation Time:24 h
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Result:Caused a significant rise in early apoptotic cell populations (Annexin V+PI−) and late apoptotic cell populations (Annexin V+PI+).
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Cell Line:A375, SK-MEL-28, SK-MEL-5
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Concentration:2.5-5 μM
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Incubation Time:24 h
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Result:Increased expression of pro-apoptotic proteins BAX, cleaved caspase-3, and cleaved caspase-9.
Downregulated anti-apoptotic factor BCL-2.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6 (8-week-old female; subcutaneous injection of 5 × 105 B16F10 melanoma cells)[1]
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Dosage:10 mg/kg; 20 mg/kg
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Administration:p.o.; daily; 10 days
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Result:Significantly reduced tumor volume compared to vehicle control.
Increased tumor-infiltrating CD8+ T cells from 5.03% to 17.9% of CD3+ cells.
Increased CD4+ T cells from ~5% to ~10% of CD3+ cells.
Increased NK1.1+ cells from ~2% to ~4% of CD45+ cells.
Caused no significant changes in mouse body weight during treatment.
Chemical Information
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CAS No. 94134-60-8
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Molecular Weight 392.39
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Formula C19H25N2O5P
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SMILES
C(C)[C@]12[C@]3(C=4N(C=5C(C4CCN3CCC1)=CC=CC5)C(=O)C2)[H].P(=O)(O)(O)O
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Synonyms
(-)-Eburnamonine phosphate; (-)-Vincamone phosphate
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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]. Zhu S, et al. Vinburnine potentiates anti-PD1 immunotherapy in melanoma through IL-24 secretion via P38/MAPK/ATF3 signaling. Journal of experimental & clinical cancer research : CR. 2025 Aug 27;44(1):255. [Content Brief]
[2]. Fandy TE, et al. In vitro characterization of transport and metabolism of the alkaloids: vincamine, vinpocetine and eburnamonine. Cancer chemotherapy and pharmacology. 2016 Feb;77(2):259-67. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Vinburnine phosphate Related Classifications
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