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Art. -Nr.: HY-121064

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Affinisine

Affinisine is an indole alkaloid present in Alstonia macrophylla and Tabernaemontana catharinensis. Affinisine induces apoptosis, cell cycle arrest and reduces cell viability in melanoma cells. Affinisine can be used in studies related to cancers such as melanoma, glioma and breast cancer.

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CAS. Nr.: 2912-11-0
Formel: C₂₀H₂₄N₂O
Molecular Weight:308.42

Speicherung:

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

Affinisine Chemical Structure

CAS. Nr.: 2912-11-0

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Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

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

Biologische Aktivität

Beschreibung

Cellular Effect

Cell Line	Type	Value	Description	References
A-375	IC50	75.04 μg/mL	Cytotoxicity against human A375 melanoma cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay. Cytotoxicity against human A375 melanoma cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay.	31255990
SK-MEL-28	IC50	57.84 μg/mL	Cytotoxicity against human SK-MEL-28 melanoma cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay. Cytotoxicity against human SK-MEL-28 melanoma cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay.	31255990
A-375	IC50	57.69 μg/mL	Cytotoxicity against human A375 melanoma cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay. Cytotoxicity against human A375 melanoma cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay.	31255990
SK-MEL-28	IC50	41.51 μg/mL	Cytotoxicity against human SK-MEL-28 melanoma cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay. Cytotoxicity against human SK-MEL-28 melanoma cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay.	31255990

In Vitro

Affinisine (compound 14) (up to 30 μg/mL; 72 h) was not evaluated in cytotoxicity or multidrug resistance reversal assays using Vincristine (HY-N0488A)-sensitive KB/S, Vincristine-resistant KB/VJ300, or Vincristine-resistant KB/VJ300 cells co-treated with 0.1 μg/mL Vincristine^[1].
Affinisine (5-100 μg/mL; 24-48 h) inhibits viability of A375, WM1366, and SK-MEL-28 human melanoma cells in a dose- and time-dependent manner, with the lowest 48 h IC₅₀ of 32.86 μg/mL in WM1366 cells, and shows selectivity over normal CCD-1059Sk skin cells^[2].
Affinisine (compound 3) (48 h) moderately inhibits the growth of U251, NCI-ADR/RES, 786-0, and HT-29 human tumor cell lines after 48 h of incubation, with GI₅₀ values ranging from 8.3 μM to 9.5 μM, and shows a selectivity index of at least 1.5 relative to non-tumor HaCat keratinocytes^[3].
Affinisine (57-65 μg/mL for A375; 32-45 μg/mL for WM1366; 46-55 μg/mL for SK-MEL-28; 48 h) induces apoptosis in A375, WM1366, and SK-MEL-28 human melanoma cells after 48 h of treatment, with the highest apoptotic rate (87.16%) observed in A375 cells treated with 65 μg/mL^[2].
Affinisine (57-65 μg/mL for A375; 32-45 μg/mL for WM1366; 46-55 μg/mL for SK-MEL-28; 48 h) induces G₂/M phase arrest in A375 human melanoma cells and G₀/G₁ phase arrest in WM1366 human melanoma cells after 48 h of treatment, but does not affect cell cycle progression in SK-MEL-28 human melanoma cells^[2].

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

Cell Cytotoxicity Assay^[1]

Cell Line:

Vincristine-sensitive human oral epidermoid carcinoma KB/S cells, Vincristine-resistant human oral epidermoid carcinoma KB/VJ300 cells, Vincristine-resistant KB/VJ300 cells treated with 0.1 μg/mL Vincristine
Concentration:

Up to 30 μg/mL; 0.1 μg/mL (KB/VJ300(+) group)
Incubation Time:

72 h
Result:

Was not tested in the cytotoxicity or multidrug resistance reversal assay.
Had no available data from these assays.

Cell Cytotoxicity Assay^[2]

Cell Line:

A375, WM1366, SK-MEL-28, CCD-1059Sk
Concentration:

5 μg/mL; 10 μg/mL; 25 μg/mL; 50 μg/mL; 100 μg/mL
Incubation Time:

24 h; 48 h
Result:

Decreased cell viability in a dose- and time-dependent manner across all tested melanoma cell lines.
Reduced IC₅₀ values of A375 cells from 75.04 μg/mL at 24 h to 57.69 μg/mL at 48 h.
Reduced IC₅₀ values of WM1366 cells from 48.22 μg/mL at 24 h to 32.86 μg/mL at 48 h.
Reduced IC₅₀ values of SK-MEL-28 cells from 57.84 μg/mL at 24 h to 41.51 μg/mL at 48 h.
Resulted in a 48 h IC₅₀ of 77.81 μg/mL for normal skin cell line CCD-1059Sk, indicating selectivity toward tumor cells.

Apoptosis Analysis^[2]

Cell Line:

A375, WM1366, SK-MEL-28
Concentration:

57-65 μg/mL (A375); 32-45 μg/mL (WM1366); 46-55 μg/mL (SK-MEL-28)
Incubation Time:

48 h
Result:

Increased total apoptotic cell populations across all melanoma cell lines.
Induced 58.16% total apoptosis and 56.66% late apoptosis/dead cell rate in A375 cells at 57 μg/mL.
Induced 87.16% total apoptosis and 86.71% late apoptosis/dead cell rate in A375 cells at 65 μg/mL.
Induced 11.37% total apoptosis in WM1366 cells at 32 μg/mL.
Induced 20.06% total apoptosis in WM1366 cells at 45 μg/mL.
Induced 38.83% total apoptosis in SK-MEL-28 cells at 46 μg/mL.
Induced 60.69% total apoptosis in SK-MEL-28 cells at 55 μg/mL.

Cell Cycle Analysis^[2]

Cell Line:

A375, WM1366, SK-MEL-28
Concentration:

57-65 μg/mL (A375); 32-45 μg/mL (WM1366); 46-55 μg/mL (SK-MEL-28)
Incubation Time:

48 h
Result:

Induced cell cycle arrest in A375 and WM1366 cells, but not in SK-MEL-28 cells.
Increased G2/M phase populations of A375 cells from 8.66% in controls to 14.56% at 57 μg/mL and 14.73% at 65 μg/mL.
Increased G0/G1 phase populations of WM1366 cells from 69.56% in controls to 78% at 32 μg/mL and 77.53% at 45 μg/mL, accompanied by decreased S phase populations.

Chemical Information

CAS. Nr. 2912-11-0
Molecular Weight 308.42
Formel C₂₀H₂₄N₂O
SMILES

CN1C2=C(C3=CC=CC=C31)C[C@]4([H])[N@@]5[C@@]2([H])C[C@](/C(C5)=C\C)([H])[C@H]4CO
Structure Classification
- Alkaloids
- Monoterpene Indole Alkaloids
Initial Source
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]. Lim SH, et al. Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla. Phytochemistry. 2014 Feb;98:204-15.

[2]. Fagundes Rosales P, et al. Extraction, isolation and in vitro evaluation of affinisine from Tabernaemontana catharinensis in human melanoma cells. Bioorganic chemistry. 2019 Sep;90:103079.

[3]. Reis FL, et al. In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res. 2022 Nov;36(22):5808-5812.

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)}

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