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  3. Eupalinolide A

Eupalinolide A is a Yes-associated protein (YAP) degrader and HSP70 inducer. Eupalinolide A inhibits osteogenic differentiation of tendon-derived stem cells (TDSCs). Eupalinolide A induces autophagy in hepatocellular carcinoma cells via activating the ROS/ERK signaling pathway. Eupalinolide A protects PAM212 cells from UVB-, Menadione (HY-B0332)-, or heat shock-induced apoptosis. Eupalinolide A alleviates trauma-induced heterotopic ossification (HO) of Achilles tendon and inhibits growth of MHCC97-L and HCCLM3 hepatocellular carcinoma xenograft tumors in mice. Eupalinolide A can be used for the study of traumatic heterotopic ossification of tendons and hepatocellular carcinoma.

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Eupalinolide A

Eupalinolide A Chemical Structure

CAS No. : 877822-40-7

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Based on 1 publication(s) in Google Scholar

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Description

Eupalinolide A is a Yes-associated protein (YAP) degrader and HSP70 inducer. Eupalinolide A inhibits osteogenic differentiation of tendon-derived stem cells (TDSCs). Eupalinolide A induces autophagy in hepatocellular carcinoma cells via activating the ROS/ERK signaling pathway. Eupalinolide A protects PAM212 cells from UVB-, Menadione (HY-B0332)-, or heat shock-induced apoptosis. Eupalinolide A alleviates trauma-induced heterotopic ossification (HO) of Achilles tendon and inhibits growth of MHCC97-L and HCCLM3 hepatocellular carcinoma xenograft tumors in mice. Eupalinolide A can be used for the study of traumatic heterotopic ossification of tendons and hepatocellular carcinoma[1][2][3].

In Vitro

Eupalinolide A (1-10 μM, 7-14 d) dose-dependently inhibits osteogenic differentiation of tendon-derived stem cells (TDSCs), as evidenced by decreased alkaline phosphatase (ALP) activity, reduced calcium deposition, downregulated mRNA expression of osteogenic genes (Alp, Col1a1, Osx, Ocn, Opn), and decreased protein levels of OSX and OCN[1].
Eupalinolide A (10 μM) induces YAP degradation via TOLLIP-mediated selective autophagy and Promotes K27-linked polyubiquitination of YAP in HEK293T cells[1].
Eupalinolide A (28 μM, 48 h) reduces BrdU-positive cells and inhibits DNA synthesis in MHCC97-L and HCCLM3 cells via BrdU staining[2].
Eupalinolide A (28 μM, 21 d) decreases colony number and size of MHCC97-L and HCCLM3 cells[2].
Eupalinolide A (7-28 μM, 24-48 h) suppresses migration and reverses EMT of MHCC97-L and HCCLM3 cells[2].
Eupalinolide A (7-28 μM, 48 h) induces G1 phase arrest and autophagy, and increases ROS production in MHCC97-L and HCCLM3 cells[2].
Eupalinolide A (5-10 μg/mL, 24 h) induces HSP70 expression in B16 mouse melanoma cells and PAM212 mouse squamous cell carcinoma cells[3].
Eupalinolide A (2.5-10 μg/mL, 24 h) induces the expression of HSP25, HSP40, and HSP90 (HSP90α) at both protein and mRNA levels in PAM212 cells[3].
Eupalinolide A (5-10 μg/mL, 3 h) promotes phosphorylation and nuclear translocation of HSF1 in PAM212 cells and inhibits the interaction between HSF1 and HSP90[3].
Eupalinolide A (5-10 μg/mL, 24 h) suppresses IBMX (HY-12318)-induced melanin production, tyrosinase activity and downregulates tyrosinase, Tyrp1, and Dct mRNA/protein levels in B16 cells[3].

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

Western Blot Analysis[2]

Cell Line: MHCC97-L and HCCLM3 cells
Concentration: 7, 14, 28 μM
Incubation Time: 48 h
Result: Upregulated E-cadherin, N-cadherin, fibronectin, p-ERK and ZEB1.
Downregulated Vimentin in MHCC97-L and HCCLM3 cells.
Downregulated CDK2, CDK4, Cyclin E1, and Cyclin D1.
Upregulated LC3 II/I/Atg5 and downregulated p62.

Cell Cycle Analysis[2]

Cell Line: MHCC97-L and HCCLM3 cells
Concentration: 14, 28 μM
Incubation Time: 48 h
Result: Induced G1 phase arrest in MHCC97-L and HCCLM3 cells.
In Vivo

Eupalinolide A (1-10 μM, local injection, 20 μL/mouse, once weekly for 8 weeks) dose-dependently alleviates trauma-induced heterotopic ossification (HO) of Achilles tendon in mice[1].
Eupalinolide A (30-60 mg/kg, i.p., once daily, 3 weeks) inhibits growth of MHCC97-L and HCCLM3 hepatocellular carcinoma xenograft tumors in female nude mice[2].

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

Animal Model: 8-week-old male C57BL/6 mice[1]
Dosage: 1, 5, 10 μM
Administration: local injection, 20 μL/mouse, once weekly for 8 weeks
Result: Rduced ectopic bone volume in Achilles tendon.
Dcreased calcified areas.
Dwnregulated mRNA expression of osteogenic genes (Runx2, Alp, Osx, Ocn, Opn, Col1a1) and protein levels of OSX and OCN.
Ihibited YAP protein expression in Achilles tendon.
Animal Model: MHCC97-L cells and HCCLM3 cells (1 × 106) were subcutaneously implanted into the flanks of 4-week-old female BALB/c nude mice[2]
Dosage: 30, 60 mg/kg
Administration: i.p., once daily, 3 weeks
Result: Achieved tumor growth inhibition (TGI).
Molecular Weight

462.49

Formula

C24H30O9

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=C(O[C@@H]1C/C(COC(C)=O)=C\C[C@H](OC(C)=O)/C(C)=C\[C@@]([C@]1([H])C2=C)([H])OC2=O)/C(C)=C/CO

Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility
In Vitro: 

DMSO : 100 mg/mL (216.22 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 2.1622 mL 10.8110 mL 21.6221 mL
5 mM 0.4324 mL 2.1622 mL 4.3244 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (5.41 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (5.41 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
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Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 2.1622 mL 10.8110 mL 21.6221 mL 54.0552 mL
5 mM 0.4324 mL 2.1622 mL 4.3244 mL 10.8110 mL
10 mM 0.2162 mL 1.0811 mL 2.1622 mL 5.4055 mL
15 mM 0.1441 mL 0.7207 mL 1.4415 mL 3.6037 mL
20 mM 0.1081 mL 0.5406 mL 1.0811 mL 2.7028 mL
25 mM 0.0865 mL 0.4324 mL 0.8649 mL 2.1622 mL
30 mM 0.0721 mL 0.3604 mL 0.7207 mL 1.8018 mL
40 mM 0.0541 mL 0.2703 mL 0.5406 mL 1.3514 mL
50 mM 0.0432 mL 0.2162 mL 0.4324 mL 1.0811 mL
60 mM 0.0360 mL 0.1802 mL 0.3604 mL 0.9009 mL
80 mM 0.0270 mL 0.1351 mL 0.2703 mL 0.6757 mL
100 mM 0.0216 mL 0.1081 mL 0.2162 mL 0.5406 mL
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