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Purity: ≥98%
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.
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].
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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].
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Animal Protocol |
9L-V6R cells are injected into the brains of Fischer 344 rats;
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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 |
Molecular Formula |
C19H26O3
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Molecular Weight |
302.4079
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CAS # |
362-07-2
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Related CAS # |
2-Methoxyestradiol-13C,d3;1217470-09-1;2-Methoxyestradiol-13C6;2-Methoxyestradiol-d5;358731-34-7
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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
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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
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Synonyms |
NSC 659853; NSC-659853; NSC659853; 2-ME; 2-Methoxy Estradiol. 2-methoxyestradiol; US brand name: Panzem. Abbreviation: 2-ME2.
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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)
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Solubility (In Vitro) |
DMSO: 60 mg/mL (198.4 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.88 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.88 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (6.88 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 2% DMSO+corn oil:5mg/mL |
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.
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.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT00592579 | Completed | Drug: 2-methoxyestradiol | Relapsed Multiple Myeloma Plateau Phase Multiple Myeloma |
CASI Pharmaceuticals, Inc | March 2001 | Phase 2 |
NCT00306618 | Completed | Drug: Panzem Nanocrystal Colloidal Dispersion |
Recurrent Glioblastoma Multiforme | CASI Pharmaceuticals, Inc. | January 2006 | Phase 2 |
NCT00328497 | Completed | Drug: Panzem (2-methoxyestradiol) NCD, Avastin (Bevacizumab) |
Carcinoid Tumor | CASI Pharmaceuticals, Inc. | May 2006 | Phase 2 |
NCT00481455 | Completed | Drug: Panzem NCD Drug: Temozolomide |
Recurrent Glioblastoma Multiforme | CASI Pharmaceuticals, Inc. | April 2007 | Phase 2 |
Treatment of 9L rat glioma cells with 2-methoxyestradiol (2ME2) at different oxygen concentration. Cancer Res. 2006 Dec 15;66(24):11991-7. td> |
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. td> |
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. td> |