Linichlorin A
Linichlorin A is a p27Kip1 ubiquitination inhibitor that blocks p27Kip1 degradation by inhibiting the Skp2-Cks1–p27Kip1 interaction. Linichlorin A shows selective antiproliferative activity against tumor cells. Linichlorin A induces apoptosis in leukemia cells via cytochrome c release, caspase activation and PARP cleavage. Linichlorin A can be used in the study of leukemia, melanoma, cervical cancer and breast cancer.
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- No. CAS: 62462-98-0
- Fòrmula: C19H23ClO6
- Peso molecular:382.84
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Almacenamiento:
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Actividad biológica
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Caspase-3 |
Caspase-7 |
Caspase-8 |
Caspase-9 |
CDK |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| NIH3T3 | IC50 |
12.7 μM
Compound: Linichlorin A
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Antiproliferative activity against mouse NIH/3T3 cells
Antiproliferative activity against mouse NIH/3T3 cells
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30108998 |
| HeLa | IC50 |
3.2 μM
Compound: Linichlorin A
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Antiproliferative activity against human HeLa cells
Antiproliferative activity against human HeLa cells
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30108998 |
| HL-60 | IC50 |
1.2 μM
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Shows growth inhibitory activity against HL-60 cells.
Shows growth inhibitory activity against HL-60 cells.
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33371413 |
| U-937 | IC50 |
1.9 μM
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Shows growth inhibitory activity against U-937 cells.
Shows growth inhibitory activity against U-937 cells.
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33371413 |
| SK-MEL-1 | IC50 |
3.6 μM
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Shows growth inhibitory activity against SK-MEL-1 cells.
Shows growth inhibitory activity against SK-MEL-1 cells.
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33371413 |
Linichlorin A (72 h) shows growth inhibitory activity against HL-60, U-937, U-937/Bcl-2 and SK-MEL-1 cells with IC50 values of 1.2, 1.9, 2.9 and 3.6 μM, respectively[1].
Linichlorin A (48 h) shows selective antiproliferative activity against HeLa, tsFT210 and NIH3T3 cells with IC50 values of 3.2, 1.6 and 12.7 μM, respectively[2].
Linichlorin A (10 μM; 24 h) induces significant morphological changes and a marked reduction in cell number in HL-60, U-937, U-937/Bcl-2 and SK-MEL-1 cells as observed by inverted phase-contrast microscopy[1].
Linichlorin A (10 μM; 24 h) induces typical apoptosis in U-937 cells as determined by flow cytometry: the sub-G1 apoptotic cell fraction increases significantly, and Annexin V-FITC staining reveals phosphatidylserine externalization[1].
Linichlorin A (10 μM; 24 h) stimulates caspase activity and processing in U-937 cells (caspase-9, -8 and -3/7 activities increase approximately 4-, 3- and 7-fold, respectively; Western blotting shows processing of pro-caspase-3, -8 and -9), and induces downstream PARP cleavage (116 kDa → 85 kDa)[1].
Linichlorin A (3 μM and 10 μM; 24 h) induces concentration-dependent release of cytochrome c from mitochondria to cytosol in U-937 cells, with 3 μM being sufficient[1].
Linichlorin A (10 μM; 24 h) still induces apoptosis (sub-G₁ fraction increases approximately 11-fold) in Bcl-2-overexpressing U-937/Bcl-2 cells, and Bcl-2 overexpression does not confer significant protection[1].
Linichlorin A (60 μg/mL) inhibits the binding of Skp2-Cks1 to p27Kip1 phosphopeptides in a fluorescence-based high-throughput screening assay[2].
Linichlorin A (3.2 μM) inhibits the in vitro ubiquitination of p27Kip1 (approximately 70-80% reduction)[2].
Linichlorin A (3.2 μM; 18 h) stabilizes p27Kip1 protein levels by inhibiting its degradation in HeLa cells, without affecting p27Kip1 mRNA expression[2].
Linichlorin A (1-10 μM; 18 h) upregulates p27Kip1 protein expression in tsFT210 cells in a dose-dependent manner[2].
Linichlorin A (1.6 μM; 8-12 h) delays G1-S phase progression and significantly increases p27Kip1 protein levels in tsFT210 cells[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HL-60, U-937, U-937/Bcl-2 and SK-MEL-1 cells
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Concentration:1, 10, 30 and 100 μM
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Incubation Time:72 h
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Result:Showed growth inhibitory activity with IC50 values of 1.2, 1.9, 2.9 and 3.6 μM, respectively.
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Cell Line:U-937 and HL-60 cells
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Concentration:10 μM
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Incubation Time:24 h
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Result:Showed fragmented and condensed chromatin characteristic of apoptotic cell death after Hoechst 33258 staining.
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Cell Line:U-937 and HL-60 cells
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Concentration:10 μM
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Incubation Time:24 h
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Result:Significantly increased the percentage of apoptotic cells in the sub-G₁ fraction (approximately 12-fold in U-937 and 13-fold in HL-60 compared with control) as determined by flow cytometry after propidium iodide staining.
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Cell Line:U-937 cells (and U-937/Bcl-2 for the last result)
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Concentration:10 μM
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Incubation Time:24 h
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Result:Induced phosphatidylserine externalization (Annexin V‑FITC positive); stimulated caspase‑9, ‑8 and ‑3/7 activities (approximately 4‑, 3‑ and 7‑fold increases, respectively, by colorimetric substrates); in Bcl‑2‑overexpressing U‑937/Bcl‑2 cells, still induced apoptosis (approximately 11‑fold increase in sub‑G₁ fraction) without significant protection.
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Cell Line:U-937 cells
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Concentration:10 μM (for PARP and caspase processing) / 3 μM and 10 μM (for cytochrome c)
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Incubation Time:24 h
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Result:Induced PARP cleavage (116 kDa full-length to 85 kDa fragment); induced concentration‑dependent release of cytochrome c from mitochondria to cytosol (3 μM was sufficient); showed processing of pro‑caspase‑3, ‑8 and ‑9.
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Cell Line:tsFT210 cells
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Concentration:1.6 μM
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Incubation Time:8 h and 12 h
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Result:Delayed G₁‑S phase progression in tsFT210 cells. After G₂ synchronization at 39°C for 18 h, cells released at 32°C showed a decreased percentage of S phase cells at 8 h and 12 h compared with control, as determined by flow cytometry after propidium iodide staining.
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Cell Line:HeLa cells
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Concentration:3.2 μM
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Incubation Time:18 h
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Result:Showed no significant effect on p27Kip1 mRNA expression level compared with DMSO control, as determined by semi‑quantitative RT‑PCR.
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Cell Line:HeLa cells
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Concentration:3.2 μM
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Incubation Time:18 h
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Result:Inhibited p27Kip1 degradation and stabilized its protein level in the CHX chase assay.
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Cell Line:tsFT210 cells
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Concentration:1, 3 and 10 μM (for dose‑dependent study); 1.6 μM (for cell cycle study)
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Incubation Time:18 h (for dose‑dependent study); 8‑12 h (for cell cycle study)
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Result:Upregulated p27Kip1 protein expression in a dose‑dependent manner at 1‑10 μM for 18 h; significantly increased p27Kip1 protein levels during G₁‑S progression at 1.6 μM for 8‑12 h.
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Cell Line:NIH3T3 cells
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Concentration:10 μM
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Incubation Time:18 h
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Result:Showed lower p27Kip1 upregulation compared with tsFT210 cells.
Chemical Information
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No. CAS 62462-98-0
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Peso molecular 382.84
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Fòrmula C19H23ClO6
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SMILES
C(Cl)[C@]1(O)[C@@]2([C@@]3([C@@]([C@@H](OC(C(C)=C)=O)CC(=C)[C@@]2(C[C@@H]1O)[H])(C(=C)C(=O)O3)[H])[H])[H]
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Please store the product under the recommended conditions in the Certificate of Analysis.
Pureza y Documentación
Referencias
[1]. Estévez-Sarmiento F, et al. Chlorinated Guaiane-Type Sesquiterpene Lactones as Cytotoxic Agents against Human Tumor Cells. Int J Mol Sci. 2020 Dec 21;21(24):9767. [Content Brief]
[2]. Ooi LC, et al. Identification of small molecule inhibitors of p27(Kip1) ubiquitination by high-throughput screening. Cancer Sci. 2013 Nov;104(11):1461-7. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Linichlorin A Related Classifications
HY-126757 Related Classifications
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- Linichlorin A
- 62462-98-0
- Caspase
- Apoptosis
- PARP
- p27Kip1
- p27Kip1 ubiquitination inhibitor
- apoptosis
- caspase activation
- HL-60
- U-937
- U-937/Bcl-2
- SK-MEL-1
- growth inhibition
- caspase activation
- PARP cleavage
- cytochrome c release
- leukemia
- melanoma
- HeLa
- tsFT210
- NIH3T3
- Skp2
- Cks1
- ubiquitination
- cell cycle
- G? S phase
- CHX chase assay
- protein stability
- mRNA expression
- high throughput screening
- anticancer
- Inhibitor
- inhibitor
- inhibit