Art. -Nr.: HY-126757

Linichlorin A

Linichlorin A is a p27^Kip1 ubiquitination inhibitor that blocks p27^Kip1 degradation by inhibiting the Skp2-Cks1–p27^Kip1 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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CAS. Nr.: 62462-98-0
Formel: C₁₉H₂₃ClO₆
Molecular Weight:382.84

Speicherung:

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

Linichlorin A Chemical Structure

CAS. Nr.: 62462-98-0

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

Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
Reinheit & Dokumentation
Verweise
Calculators
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target^[1]

Caspase-3

Caspase-7

Caspase-8

Caspase-9

CDK

Alle Caspase Isoform-spezifische Produkte anzeigen :

Alle PARP Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
NIH3T3	IC₅₀	12.7 μM Compound: Linichlorin A	Antiproliferative activity against mouse NIH/3T3 cells Antiproliferative activity against mouse NIH/3T3 cells	30108998
HeLa	IC₅₀	3.2 μM Compound: Linichlorin A	Antiproliferative activity against human HeLa cells Antiproliferative activity against human HeLa cells	30108998
HeLa	IC₅₀	3.2 μM Compound: Linichlorin A	Antiproliferative activity against human HeLa cells Antiproliferative activity against human HeLa cells	[PMID: 30108998]
NIH3T3	IC₅₀	12.7 μM Compound: Linichlorin A	Antiproliferative activity against mouse NIH/3T3 cells Antiproliferative activity against mouse NIH/3T3 cells	[PMID: 30108998]
HL-60	IC50	1.2 μM	Shows growth inhibitory activity against HL-60 cells. Shows growth inhibitory activity against HL-60 cells.	33371413
U-937	IC50	1.9 μM	Shows growth inhibitory activity against U-937 cells. Shows growth inhibitory activity against U-937 cells.	33371413
SK-MEL-1	IC50	3.6 μM	Shows growth inhibitory activity against SK-MEL-1 cells. Shows growth inhibitory activity against SK-MEL-1 cells.	33371413

In Vitro

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 p27^Kip1 phosphopeptides in a fluorescence-based high-throughput screening assay^[2].
Linichlorin A (3.2 μM) inhibits the in vitro ubiquitination of p27^Kip1 (approximately 70-80% reduction)^[2].
Linichlorin A (3.2 μM; 18 h) stabilizes p27^Kip1 protein levels by inhibiting its degradation in HeLa cells, without affecting p27^Kip1 mRNA expression^[2].
Linichlorin A (1-10 μM; 18 h) upregulates p27^Kip1 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 p27^Kip1 protein levels in tsFT210 cells^[2].

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

Cell Viability Assay^[1]

Cell Line:

HL-60, U-937, U-937/Bcl-2 and SK-MEL-1 cells
Concentration:

1, 10, 30 and 100 μM
Incubation Time:

72 h
Result:

Showed growth inhibitory activity with IC₅₀ values of 1.2, 1.9, 2.9 and 3.6 μM, respectively.

Immunofluorescence^[1]

Cell Line:

U-937 and HL-60 cells
Concentration:

10 μM
Incubation Time:

24 h
Result:

Showed fragmented and condensed chromatin characteristic of apoptotic cell death after Hoechst 33258 staining.

Cell Cycle Analysis^[1]

Cell Line:

U-937 and HL-60 cells
Concentration:

10 μM
Incubation Time:

24 h
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.

Apoptosis Analysis^[1]

Cell Line:

U-937 cells (and U-937/Bcl-2 for the last result)
Concentration:

10 μM
Incubation Time:

24 h
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.

Western Blot Analysis^[1]

Cell Line:

U-937 cells
Concentration:

10 μM (for PARP and caspase processing) / 3 μM and 10 μM (for cytochrome c)
Incubation Time:

24 h
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.

Cell Cycle Analysis^[2]

Cell Line:

tsFT210 cells
Concentration:

1.6 μM
Incubation Time:

8 h and 12 h
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.

RT-PCR^[2]

Cell Line:

HeLa cells
Concentration:

3.2 μM
Incubation Time:

18 h
Result:

Showed no significant effect on p27^Kip1 mRNA expression level compared with DMSO control, as determined by semi‑quantitative RT‑PCR.

Western Blot Analysis^[2]

Cell Line:

HeLa cells
Concentration:

3.2 μM
Incubation Time:

18 h
Result:

Inhibited p27^Kip1 degradation and stabilized its protein level in the CHX chase assay.

Western Blot Analysis^[2]

Cell Line:

tsFT210 cells
Concentration:

1, 3 and 10 μM (for dose‑dependent study); 1.6 μM (for cell cycle study)
Incubation Time:

18 h (for dose‑dependent study); 8‑12 h (for cell cycle study)
Result:

Upregulated p27^Kip1 protein expression in a dose‑dependent manner at 1‑10 μM for 18 h; significantly increased p27^Kip1 protein levels during G₁‑S progression at 1.6 μM for 8‑12 h.

Western Blot Analysis^[2]

Cell Line:

NIH3T3 cells
Concentration:

10 μM
Incubation Time:

18 h
Result:

Showed lower p27^Kip1 upregulation compared with tsFT210 cells.

Chemical Information

CAS. Nr. 62462-98-0
Molecular Weight 382.84
Formel C₁₉H₂₃ClO₆
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]
Structure Classification
- Terpenoids
- Sesquiterpenes
Initial Source
- Animals
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]. 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

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

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Linichlorin A

Alle Caspase Isoform-spezifische Produkte anzeigen

Alle PARP Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Reinheit & Dokumentation

Verweise

Calculators

Help & FAQs

Linichlorin A Related Classifications

HY-126757 Related Classifications

Bioz