2. Apoptosis NF-κB Metabolic Enzyme/Protease GPCR/G Protein Neuronal Signaling
  3. Apoptosis NF-κB MMP Adrenergic Receptor
  4. Eupatorin

Eupatorin is an orally active flavonoid with antiproliferative and vasodilatory properties. Eupatorin downregulates the expression levels of NF-κB, MMP9, IL-1β and TNF-α. Eupatorin induces apoptosis, G2/M phase cell cycle arrest, and reactive oxygen species (ROS) production. Eupatorin modulates the activities of muscarinic receptors and β-adrenergic receptors; inhibits sarcoplasmic reticulum calcium release and calcium channels; and activates the NO/sGC/cGMP pathway, indomethacin-sensitive pathway, and potassium channel pathway. Eupatorin exerts cytotoxic effects on cancer cell lines, and is metabolized by CYP1A1 and CYP1 family enzymes to form metabolites with antiproliferative activity. Eupatorin can be used in research related to breast cancer, hypertension, and leukemia.

For research use only. We do not sell to patients.

Eupatorin

Eupatorin Chemical Structure

CAS No. : 855-96-9

Size Price Stock Quantity
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO
ready for reconstitution
 In-stock
Solution
10 mM * 1 mL in DMSO In-stock
Solid
5 mg In-stock
10 mg In-stock
50 mg   Get quote  
100 mg   Get quote  

* Please select Quantity before adding items.

This product is a controlled substance and not for sale in your territory.

Customer Review

Based on 2 publication(s) in Google Scholar

Other Forms of Eupatorin:

Eupatorin Related Antibodies

Top Publications Citing Use of Products

View All NF-κB Isoform Specific Products:

View All Isoforms
NF-κB NF-κB1/p50 RelA/p65 RelB c-Rel

View All MMP Isoform Specific Products:

View All Isoforms
MMP-1 MMP-2 MMP-3 MMP-8 MMP-9 MMP-13 MMP-14 MMP-17 ADAM10 ADAM17 MMP-7 MMP-12 MMP-10 MMP ADAM8 MMP-19

View All Adrenergic Receptor Isoform Specific Products:

View All Isoforms
α adrenergic receptor β adrenergic receptor

  • Biological Activity

  • Purity & Documentation

  • References

  • Customer Review

Description

Eupatorin is an orally active flavonoid with antiproliferative and vasodilatory properties. Eupatorin downregulates the expression levels of NF-κB, MMP9, IL-1β and TNF-α. Eupatorin induces apoptosis, G2/M phase cell cycle arrest, and reactive oxygen species (ROS) production. Eupatorin modulates the activities of muscarinic receptors and β-adrenergic receptors; inhibits sarcoplasmic reticulum calcium release and calcium channels; and activates the NO/sGC/cGMP pathway, indomethacin-sensitive pathway, and potassium channel pathway. Eupatorin exerts cytotoxic effects on cancer cell lines, and is metabolized by CYP1A1 and CYP1 family enzymes to form metabolites with antiproliferative activity. Eupatorin can be used in research related to breast cancer, hypertension, and leukemia[1][2][3][4].

Cellular Effect
Cell Line Type Value Description References
HT-1080 ED50
8.8 μg/mL
Compound: c
Antiproliferative activity against human HT1080 cells after 4 days by MTT assay
Antiproliferative activity against human HT1080 cells after 4 days by MTT assay
[PMID: 11374950]
HeLa IC50
8.1 μM
Compound: Eupatorin
Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay
Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay
[PMID: 31784199]
KB ED50
> 50 μg/mL
Compound: 6
Cytotoxicity against human KB cells
Cytotoxicity against human KB cells
[PMID: 521819]
MCF7 IC50
10.3 μM
Compound: Eupatorin
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay
[PMID: 31784199]
MCF7 IC50
7 μM
Compound: 1
Antiproliferative activity in human MCF7 cells after 96 hrs by MTT assay
Antiproliferative activity in human MCF7 cells after 96 hrs by MTT assay
[PMID: 19601638]
In Vitro

Eupatorin (0.16-20 μg/mL; 24-72 h) inhibits proliferation of mouse breast cancer 4T1 cells in a time-dependent manner, with IC50 values of >20 μg/mL at 24 h, 6.00 μg/mL at 48 h, and 5.00 μg/mL at 72 h[1].
Eupatorin (0.001-100 μM; 96 h) potently inhibits proliferation of MDA-MB-468 cells with an IC50 of 0.5 μM, while being far less active in MCF-10A cells with an IC50 of 50 μM; its antiproliferative effect in MDA-MB-468 cells is reversed by CYP1 inhibition[3].
Eupatorin (10 μM; 48 h) induces G2/M phase arrest in MDA-MB-468 cells, an effect reversed by CYP1 inhibition, while it does not affect the cell cycle of MCF-10A cells[3].
Eupatorin (0.1-100 μM; 72 h) potently inhibits viability in HL-60, U937, and Molt-3 human leukemia cell lines with an IC50 of ~5 μM after 72 h of treatment[4].
Eupatorin (3-30 μM; 6-24 h) induces apoptosis in HL-60, U937, and Molt-3 human leukemia cell lines via G2-M cell cycle arrest, nuclear fragmentation, DNA laddering, and phosphatidylserine externalization, with 3 μM eupatorin for 24 h driving significant increases in sub-diploid apoptotic cells[4].
Eupatorin (1-10 μM; 6-24 h) induces dose- and time-dependent activation of initiator (caspase-8, -9) and executioner (caspase-3/7, -6, -4) caspases, as well as PARP cleavage, in HL-60, U937, and Molt-3 human leukemia cell lines, with eupatorin-induced apoptosis dependent on caspase activation[4].
Eupatorin (1-3 μM; 24 h) activates the intrinsic mitochondrial apoptotic pathway in HL-60, U937, and Molt-3 human leukemia cell lines via release of cytochrome c, AIF, and Smac/DIABLO, modulation of Bcl-2 family proteins, and Bax translocation/cleavage[4].
Eupatorin (3-10 μM; 1-24 h) activates the ERK1/2 and JNK/SAPK MAPK pathways in HL-60 human leukemia cells within 1-2 h, with JNK/SAPK activation essential for eupatorin-induced apoptosis[4].
Eupatorin (1-10 μM; 6-24 h) induces ROS generation (peroxides and superoxide) in HL-60 and Molt-3 human leukemia cells, with ROS generation essential for eupatorin-induced apoptosis in Molt-3 cells[4].

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

Eupatorin Related Antibodies

Cell Cytotoxicity Assay[1]

Cell Line: mouse breast cancer 4T1 cells
Concentration: 0.16-20 μg/mL (24 h); 0.16-20 μg/mL (48 h); 0.16-20 μg/mL (72 h)
Incubation Time: 24 h; 48 h; 72 h
Result: Caused time- and concentration-dependent inhibition of 4T1 cell proliferation.
Yielded an IC50 value greater than 20 μg/mL at 24 h.
Yielded an IC50 value of 6.00 μg/mL at 48 h.
Yielded an IC50 value of 5.00 μg/mL at 72 h.

Cell Proliferation Assay[3]

Cell Line: MDA-MB-468, MCF-10A
Concentration: 0.001-100 μM; 10 μM (co-incubated with acacetin)
Incubation Time: 96 h
Result: Showed a dose-dependent inhibitory effect on MDA-MB-468 cell growth with an IC50 of 0.5 μM.
Reached an IC50 of 50 μM in MCF-10A cells.
Increased the IC50 to 15 μM in MDA-MB-468 cells when co-incubated with acacetin, reversing the antiproliferative effect.

Cell Cycle Analysis[3]

Cell Line: MDA-MB-468, MCF-10A
Concentration: 10 μM; 10 μM (co-incubated with 1.5 μM acacetin)
Incubation Time: 30 h, 48 h; 48 h (co-incubated with acacetin)
Result: Caused G2/M phase arrest in MDA-MB-468 cells, with ~70% of cells accumulating in G2/M phase after 48 hours, accompanied by a minor increase in sub-G1 apoptotic cells.
Reduced the percentage of MDA-MB-468 cells in G2/M phase from 70% to 40% when co-treated with acacetin, reversing the G2/M arrest.
Showed no cell cycle arrest in MCF-10A cells, though a small fraction of cells (5% at 30 h, 6% at 48 h) showed sub-G1 apoptosis.

Cell Viability Assay[4]

Cell Line: HL-60, U937, Molt-3 human leukemia cell lines
Concentration: 0.1, 1, 10, 100 μM
Incubation Time: 72 h
Result: Caused concentration-dependent inhibition of cell viability, with an IC50 of ~5 μM across the three cell lines.

Apoptosis Analysis[4]

Cell Line: HL-60, U937, Molt-3 human leukemia cell lines
Concentration: 3 μM; 10 μM; 30 μM
Incubation Time: 6, 12, 24 h (3 μM); 24 h (10 μM, 30 μM)
Result: Induced nuclear condensation and fragmented chromatin characteristic of apoptosis after 24 h at 3 μM.
Induced DNA fragmentation in HL-60 and Molt-3 cells after 24 h at 10 and 30 μM.
Caused G2-M phase accumulation starting at 6 h, with the arrest most pronounced in U937 cells, sustained until 12 h in HL-60 and U937, and not sustained in Molt-3 at 3 μM; the percentage of sub-G1 (apoptotic) cells increased after 12 h in all three cell lines.
Induced phosphatidylserine translocation (early apoptosis) in HL-60 and U937 cells after 24 h at 3 μM, with sub-diploid cell percentages increasing ~20-fold in U937, ~2-fold in HL-60, and ~3-fold in Molt-3 compared to controls.

Western Blot Analysis[4]

Cell Line: HL-60, U937, Molt-3 human leukemia cell lines
Concentration: 1 μM (Molt-3 cells); 3 μM (HL-60, U937 cells)
Incubation Time: 24 h
Result: Induced a significant increase in cytosolic cytochrome c levels, and also induced cytosolic release of AIF and Smac/DIABLO.
Decreased Bcl-2 expression in HL-60 and Molt-3 cells, and induced Bcl-2 cleavage in U937 cells.
Induced redistribution of Bax from the cytosolic to mitochondrial compartment, and generated an 18 kDa Bax cleavage fragment in HL-60 cells.
Decreased Bid protein levels in HL-60 and Molt-3 cells, indicating cleavage/activation.
In Vivo

Eupatorin (5-20 mg/kg; p.o.; daily; 28 days) at 20 mg/kg body weight significantly reduces 4T1 breast tumor weight by 24.4%, increases tumor apoptosis 15-fold, enhances NK and CD8+ T cell-mediated cytotoxicity against 4T1 cells, and reduces lung metastasis by 92.3% in BALB/c mice[1].

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

Animal Model: BALB/c (female, 4-5 weeks old, 20-22 g, orthotopic injection of 1×105 4T1 mouse mammary carcinoma cells)[1]
Dosage: 5 mg/kg; 20 mg/kg
Administration: p.o.; daily; 28 days
Result: Increased apoptotic tumor cells 5-fold relative to untreated controls at 5 mg/kg.
Achieved NK1.1+CD3- cell population of 2.97 %, NK1.1+CD3+ cell population of 2.70%, CD3+CD8+ cell population of 6.70 %, and CD3+CD4+ cell population of 11.76% at 5 mg/kg.
Molecular Weight

344.32

Formula

C18H16O7
CAS No.
Appearance

Solid

Color

Light yellow to yellow

SMILES

O=C1C=C(C2=CC=C(OC)C(O)=C2)OC3=CC(OC)=C(OC)C(O)=C13
Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 250 mg/mL (726.07 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 2.9043 mL 14.5214 mL 29.0428 mL
5 mM 0.5809 mL 2.9043 mL 5.8085 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. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Molarity Calculator

  • Dilution Calculator

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

Mass
=
Concentration
×
Volume
×
Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

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: ≥ 2.08 mg/mL (6.04 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 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% Corn Oil

    Solubility: ≥ 2.08 mg/mL (6.04 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
% 
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
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

Purity: 99.53%

SDS (480 KB)

COA (249 KB) HNMR (257 KB) LCMS (111 KB)

Handling Instructions (2659 KB)
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. 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 2.9043 mL 14.5214 mL 29.0428 mL 72.6069 mL
5 mM 0.5809 mL 2.9043 mL 5.8086 mL 14.5214 mL
10 mM 0.2904 mL 1.4521 mL 2.9043 mL 7.2607 mL
15 mM 0.1936 mL 0.9681 mL 1.9362 mL 4.8405 mL
20 mM 0.1452 mL 0.7261 mL 1.4521 mL 3.6303 mL
25 mM 0.1162 mL 0.5809 mL 1.1617 mL 2.9043 mL
30 mM 0.0968 mL 0.4840 mL 0.9681 mL 2.4202 mL
40 mM 0.0726 mL 0.3630 mL 0.7261 mL 1.8152 mL
50 mM 0.0581 mL 0.2904 mL 0.5809 mL 1.4521 mL
60 mM 0.0484 mL 0.2420 mL 0.4840 mL 1.2101 mL
80 mM 0.0363 mL 0.1815 mL 0.3630 mL 0.9076 mL
100 mM 0.0290 mL 0.1452 mL 0.2904 mL 0.7261 mL
  • No file chosen (Maximum size is: 1024 Kb)
  • If you have published this work, please enter the PubMed ID.
  • Your name will appear on the site.

Eupatorin Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Eupatorin855-96-9ApoptosisNF-κBMMPAdrenergic ReceptorNuclear factor-κBNuclear factor-kappaBMatrix metalloproteinasesBeta ReceptorERK 1/2TNF-αIL-1βMMP9CYP1A1JNK/SAPK4T1 cellsCYP1 family enzymesInhibitorinhibitorinhibit

Your Recently Viewed Products:

Inquiry Online

Your information is safe with us. * Required Fields.

Product Name

  

Requested Quantity *

Applicant Name *

 

Salutation

Email Address *

 

Phone Number *

Department

 

Organization Name *

City

State

Country or Region *

      

Remarks

Bulk Inquiry

Inquiry Information

Product Name:
Eupatorin
Cat. No.:
HY-N2374
Quantity:
MCE Japan Authorized Agent:

Customer Review

Thank You for Your Feedback!

Request for HNMR Report

Please fill out this form to request the QC report. We will send it to your Email address shortly.

Your information is safe with us. * Required Fields.

Product Name

  

Lot #

Applicant Name *

 

Email Address *

Phone Number

 

Department *

Organization Name *

 

Country or Region *

Remarks

SAFETY DATA SHEET (SDS)

English - EN (480 KB) Français - FR (480 KB) Deutsch - DE (480 KB) Norwegian - NO (480 KB) Español - ES (480 KB) Swedish - SV (480 KB) Italian - IT (480 KB) Korean - KR (480 KB) Portuguese - PT (480 KB)

Request for HNMR Report

We have received your request and will respond to you as soon as possible.