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Art. -Nr.: HY-B1180A

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Vinburnine phosphate

(Synonyms: (-)-Eburnamonine phosphate; (-)-Vincamone 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.

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CAS. Nr.: 94134-60-8
Formel: C₁₉H₂₅N₂O₅P
Molecular Weight:392.39

Speicherung:

Please store the product under the recommended conditions in the Certificate of Analysis.

Vinburnine phosphate Chemical Structure

CAS. Nr.: 94134-60-8

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

Alle p38 MAPK Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
SK-MEL-5	IC50	5 μM	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.	40866941
SK-MEL-28	IC50	5 μM	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.	40866941
A-375	IC50	5 μM	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.	40866941
B16-F10	IC50	7.5 μM	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.	40866941

In Vitro

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.

Cell Viability Assay^[1]

Cell Line:

SK-MEL-5, SK-MEL-28, A375, B16F10, PIG1
Concentration:

2.5-20 μM
Incubation Time:

24-72 h
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.

Cell Cycle Analysis^[1]

Cell Line:

A375, SK-MEL-28, SK-MEL-5
Concentration:

2.5-5 μM
Incubation Time:

24 h
Result:

Markedly arrested melanoma cells in the G0/G1 phase.

Apoptosis Analysis^[1]

Cell Line:

A375, SK-MEL-28, SK-MEL-5
Concentration:

2.5-5 μM
Incubation Time:

24 h
Result:

Caused a significant rise in early apoptotic cell populations (Annexin V+PI−) and late apoptotic cell populations (Annexin V+PI+).

Western Blot Analysis^[1]

Cell Line:

A375, SK-MEL-28, SK-MEL-5
Concentration:

2.5-5 μM
Incubation Time:

24 h
Result:

Increased expression of pro-apoptotic proteins BAX, cleaved caspase-3, and cleaved caspase-9.
Downregulated anti-apoptotic factor BCL-2.

In Vivo

Vinburnine (10-20 mg/kg; p.o.; daily; 10 days) phosphate potently inhibits melanoma tumor growth in vivo, with the 10 mg/kg dose enhancing infiltration of CD8⁺ T cells, CD4⁺ T cells, and NK cells in the tumor microenvironment without causing apparent systemic toxicity^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

C57BL/6 (8-week-old female; subcutaneous injection of 5 × 10⁵ B16F10 melanoma cells)^[1]
Dosage:

10 mg/kg; 20 mg/kg
Administration:

p.o.; daily; 10 days
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

CAS. Nr. 94134-60-8
Molecular Weight 392.39
Formel C₁₉H₂₅N₂O₅P
SMILES

C(C)[C@]12[C@]3(C=4N(C=5C(C4CCN3CCC1)=CC=CC5)C(=O)C2)[H].P(=O)(O)(O)O
Synonyms

(-)-Eburnamonine phosphate; (-)-Vincamone phosphate
Versand

Room temperature in continental US; may vary elsewhere.
Speicherung

Please store the product under the recommended conditions in the Certificate of Analysis.

Reinheit & Dokumentation

Handling Instructions (2659 KB)

Verweise

[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

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Biologische Aktivität
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Vinburnine phosphate

Alle p38 MAPK Isoform-spezifische Produkte anzeigen