2-Methoxyestradiol (2MeOE2, NSC659853, 2ME2)

Alias: NSC 659853; NSC-659853; NSC659853; 2-ME; 2-Methoxy Estradiol. 2-methoxyestradiol; US brand name: Panzem. Abbreviation: 2-ME2.
Cat No.:V0294 Purity: ≥98%
2-Methoxyestradiol (2-MeOE2, NSC-659853, 2-ME2; 2-ME), an endogenous/natural metabolite ofestradiol [17β-estradiol (E2)], is a potent inhibitor of tubulin with potential anticancer activity.
2-Methoxyestradiol (2MeOE2, NSC659853, 2ME2) Chemical Structure CAS No.: 362-07-2
Product category: Microtubule Associated
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
50mg
100mg
250mg
500mg
1g
2g
Other Sizes

Other Forms of 2-Methoxyestradiol (2MeOE2, NSC659853, 2ME2):

  • 2-Methoxyestradiol-13C,d3 (Dimethoxyestradiol 13C,d3)
  • 2-Methoxyestradiol-d5
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

2-Methoxyestradiol (2-MeOE2, NSC-659853, 2-ME2; 2-ME), an endogenous/natural metabolite of estradiol [17β-estradiol (E2)], is a potent inhibitor of tubulin with potential anticancer activity. It also acts as a blocker of HIF-1α nuclear accumulation and HIF-transcriptional activity, an inhibitor of angiogenesis as well as an inducer of apoptosis. As an inhibitor of microtubule assembly, it inhibits the polymerization of tubulin and interferes with mitotic spindle dynamics which leads to the blockage of mitosis of human cancer cells.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
2-Methoxyestradiol (2-ME) (5-100 μM) inhibits the assembly of purified tubulin in a concentration-dependent manner, with maximum inhibition (60%) at 200 μM 2-Methoxyestradiol (2ME2). 2-Methoxyestradiol strongly decreased mean microtubule growth rate, duration and length, and overall dynamics in viable interphase MCF7 cells with an IC50 (1.2 μM) of mitotic arrest. This was in line with its actions in vitro and did not appear to be related to microtubule depolymerization. 2. 2-Methoxyestradiol protects quiescent cells while inducing G2-M arrest and death in numerous cell types that are actively proliferating. 2. It has been demonstrated that large quantities of methylestradiol depolymerize microtubules in cells by binding to tubulin at or near the colchicine site and inhibiting microtubule assembly [1]. In cells cultivated under hypoxia, 2-Methoxyestradiol (2-ME) decreases HIF-1α and HIF-2α nuclear labeling. 2. Methoxyestradiol reduces the transcriptional activity and levels of HIF-1α protein. It is an anti-angiogenic, anti-proliferative, and pro-apoptotic drug. The growth rate of A549 cells treated with 10 μM 2-Methoxyestradiol was significantly reduced at 96 hours compared to DMSO-treated cells (66.2±7.2 and 101.2±2.3%, respectively; p=0.04). When cells treated with 10 μM 2-Methoxyestradiol in normoxic conditions were compared to cells under low O2 concentrations (5.8±0.2%; p=0.003), a significant increase in apoptosis was seen [2].
ln Vivo
In order to investigate the impact of 2-Methoxyestradiol (2-ME2) on the progression of uveitis, C57BL/6 mice were split into two groups at random and given an IRBP peptide vaccination. From day 0 to day 13, the 2ME2 group got intraperitoneal injections of 15 mg/kg of 2-Methoxyestradiol, whereas the control group received a vehicle. With five mice in each group, the 2-Methoxyestradiol (2ME2) group had an illness score of 0.30±0.30, considerably lower than the 2.09±0.28 in the control group (p<0.05) [3]. The administration of 60-600 mg/kg/d of 2-methylestradiol led to a dose-dependent suppression of tumor development. In comparison to the vehicle treatment group (86.5%), the 2-Methoxyestradiol-treated group had a much lower percentage of cells with strong pimonidazole-positive staining (+++) (36.0% at 60 mg/kg/d, 0% at 200 and 600 mg/kg/d). This could be because 2-Methoxyestradiol therapy significantly and dose-dependently inhibited the growth of tumors [4].
Animal Protocol
9L-V6R cells are injected into the brains of Fischer 344 rats;
References
[1]. Kamath K, et al. 2-Methoxyestradiol suppresses microtubule dynamics and arrests mitosis without depolymerizing microtubules. Mol Cancer Ther. 2006 Sep;5(9):2225-33.
[2]. Aquino-Gálvez A, et al. Effects of 2-methoxyestradiol on apoptosis and HIF-1α and HIF-2α expression in lung cancer cells under normoxia and hypoxia. Oncol Rep. 2016 Jan;35(1):577-83.
[3]. Xu L, et al. 2-Methoxyestradiol Alleviates Experimental Autoimmune Uveitis by Inhibiting Lymphocytes Proliferation and T Cell Differentiation. Biomed Res Int. 2016;2016:7948345.
[4]. Kang SH, et al. Antitumor effect of 2-methoxyestradiol in a rat orthotopic brain tumor model. Cancer Res. 2006, 66(24),11991-11997.
[5]. LaVallee TM, et al. 2-Methoxyestradiol inhibits proliferation and induces apoptosis independently of estrogen receptorsalpha and beta. Cancer Res. 2002 Jul 1;62(13):3691-7.
[6]. Chen Y, et al. Oxidative stress induces autophagic cell death independent of apoptosis in transformed and cancer cells. Cell Death Differ. 2008;15(1):171-182
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H26O3
Molecular Weight
302.4079
CAS #
362-07-2
SMILES
OC1=C(OC)C=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC2=C1
Chemical Name
(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Synonyms
NSC 659853; NSC-659853; NSC659853; 2-ME; 2-Methoxy Estradiol. 2-methoxyestradiol; US brand name: Panzem. Abbreviation: 2-ME2.
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 60 mg/mL (198.4 mM) Water:<1 mg/mL Ethanol:<1 mg/mL
Solubility (In Vivo)
2% DMSO+corn oil:5mg/mL (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3068 mL 16.5338 mL 33.0677 mL
5 mM 0.6614 mL 3.3068 mL 6.6135 mL
10 mM 0.3307 mL 1.6534 mL 3.3068 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • 2-Methoxyestradiol (2-MeOE2)

    Treatment of 9L rat glioma cells with 2-methoxyestradiol (2ME2) at different oxygen concentration. Cancer Res. 2006 Dec 15;66(24):11991-7.

  • 2-Methoxyestradiol (2-MeOE2)

    A, a representative Gd-DTPA enhanced T1-weighted MRI image from each treatment group: left, before treatment; right, after treatment. B, summary of the tumor volume from the six rats in each group; all 24 rats before and after 2-methoxyestradiol treatment were measured by noninvasive post-contrast T1-weighted MRI. C, top left, acrylic brain matrices used to slice the rat brain into a 2-mm thickness from the tip of the frontal lobe of cerebrum (Start) to match with the MRI data that were scanned in the same orientation (End; bottom left). Cancer Res. 2006 Dec 15;66(24):11991-7.

  • 2-Methoxyestradiol (2-MeOE2)

    BLIs of HIF-1 activity are shown from three representative rats of each group at the end of 2-methoxyestradiol treatment. Right, scale of light intensity. Cancer Res. 2006 Dec 15;66(24):11991-7.

Contact Us