Home>>Signaling Pathways>> Proteases>> Endogenous Metabolite>>2-Methoxyestradiol (2-MeOE2)
2-Methoxyestradiol (2-MeOE2) Catalog No.GC15084

Apoptotic, antiproliferative and antiangiogenic agent

Size Price Stock Qty
10mM (in 1mL DMSO)
$35.00
In stock
25mg
$37.00
In stock
50mg
$81.00
In stock
100mg
$127.00
In stock
300mg
$218.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Quality Control

Quality Control & SDS

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Protocol

Kinase experiment [1]:

Microtubule depolymerizing activity assay

The effects of 2-Methoxyestradiol on cellular microtubule depolymerization were determined by indirect immunofluorescence techniques in rat aortic smooth muscle A-10 cells. Microtubules were visualized using a β-tubulin antibody. Three viewers determined the percent microtubule loss for each treatment concentration. The data were averaged and plotted as percent microtubule loss versus drug concentration and the EC50s for microtubule depolymerization were calculated from the log dose-response curves.

Cell experiment [1]:

Cell lines

MDA-MB-435 and SK-OV-3 cells

Preparation method

The solubility of this compound in DMSO is > 15.3 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months.

Reacting condition

0 ~ 20 μM; 48 hrs

Applications

In breast carcinoma MDA-MB-435 cells and ovarian carcinoma SK-OV-3 cells, 2-Methoxyestradiol inhibited cellular proliferation, with IC50 values of 1.38 μM and 1.79 μM, respectively.

Animal experiment [2]:

Animal models

Rats bearing 9L-V6R cells

Dosage form

60, 200 or 600 mg/kg/d; i.p.; for 9 days

Applications

In rats bearing 9L-V6R cells, 2-Methoxyestradiol significantly decreased HIF-1 activity and inhibited tumor growth in a dose-dependent manner (4-fold reduction for 60 mg/kg/day and 23-fold reduction for 600 mg/kg/day, respectively). The immunohistochemical staining results of tumor tissues further confirmed that 2-Methoxyestradiol dose-dependently down-regulated the gross HIF-1α protein levels. However, at the dose of 600 mg/kg/day, some drug related toxicity occurred, such as diarrhea and weight loss (12 ~ 15%).

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Rao PN, Cessac JW, Tinley TL, Mooberry SL. Synthesis and antimitotic activity of novel 2-methoxyestradiol analogs. Steroids. 2002 Dec;67(13-14):1079-89.

[2]. Kang SH, Cho HT, Devi S, Zhang Z, Escuin D, Liang Z, Mao H, Brat DJ, Olson JJ, Simons JW, Lavallee TM, Giannakakou P, Van Meir EG, Shim H. Antitumor effect of 2-methoxyestradiol in a rat orthotopic brain tumor model. Cancer Res. 2006 Dec 15;66(24):11991-7.

Chemical Properties

Cas No. 362-07-2 SDF
Synonyms 2-methoxy Estradiol
Chemical Name (8R,9S,13S,14S,17S)-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Canonical SMILES CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)OC)O
Formula C19H26O3 M.Wt 302.41
Solubility ≥ 15.25 mg/mL in DMSO, ≥ 24.25 mg/mL in EtOH with ultrasonic Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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Background

2-Methoxyestradiol (2-MeOE2), an endogenous metabolite of 17β-estradiol (E2), is an inhibitor of microtubule assembly that inhibits the polymerization of tubulin and interferes with mitotic spindle dynamics leading to the blockage of mitosis of human cancer cells which lack estrogen receptors in metaphase. 2-MeOE2 is also an inhibitor of tumor growth and angiogenesis. Study results have shown that 2-MeOE2 induces mammalian cell transformation and genotoxicity in Syrian hamster embryo (SHE) fibroblasts through concentration-dependent inhibition of cell growth. Moreover, 2-MeOE2 has demonstrated anti-proliferative activity against estrogen-responsive breast cancer cell line MCF-7 and subsequent inhibition of the growth of tumors subcutaneously inoculated in mice.

Reference

[1].Takeki Tsutsui, Yukiko Tamura, Makoto Hagiwara, Takashi Miyachi, Hirohito Hikiba, Chikahiro Kubo and J. Carl Barret. Induction of mammalian cell transformation and genotoxicity by 2-methoxyestradiol, an endogenous metabolite of estrogen. Carcinogensis 2000; 21(4): 735-740
[2].Hesham Attalla, Tomi P. Makela, Herman Adlercreutz and Leif C. Anderson. 2-Methoxyestradiol arrests cells in mitosis without depolymerizing tubulin. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS 1996; 228: 467-473