2-Methoxyestradiol (2-MeOE2)
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
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
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
- 1. Anindita Das, Megan M Barry, et al. "Differential bone morphology and hypoxia activity in skeletal metastases of ER+ and ER- breast cancer." Commun Biol. 2024 Nov 21;7(1):1545 PMID: 39572705
- 2. Liu Y, Zou X, et al. "Toxoplasma gondii Cathepsin C1 inhibits NF-κB signalling through the positive regulation of the HIF-1α/EPO axis." Acta Trop. 2019 Jul;195:35-43. PMID:31004564
- 3. Bao Y, Wang Z, et al. "A feed-forward loop between nuclear translocation of CXCR4 and HIF-1α promotes renal cell carcinoma metastasis." Oncogene. 2018 Sep 3. PMID:30177838
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 302.41 |
| Cas No. | 362-07-2 |
| Formula | C19H26O3 |
| Synonyms | 2-methoxy Estradiol |
| Solubility | insoluble in H2O; ≥15.25 mg/mL in DMSO; ≥24.25 mg/mL in EtOH with ultrasonic |
| 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 |
| SDF | Download SDF |
| Canonical SMILES | O[C@@H]1[C@]2(C)[C@](CC1)([H])[C@@](CCC3=CC(O)=C4OC)([H])[C@](C3=C4)([H])CC2 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Kinase experiment [1]: | |
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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]: | |
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Cell lines |
MDA-MB-435 and SK-OV-3 cells |
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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. |
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Reacting condition |
0 ~ 20 μM; 48 hrs |
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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]: | |
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Animal models |
Rats bearing 9L-V6R cells |
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Dosage form |
60, 200 or 600 mg/kg/d; i.p.; for 9 days |
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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%). |
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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. |
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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. | |
| Description | 2-Methoxyestradiol is a natural metabolite of estradiol. | |||||
| Targets | angiogenesis | |||||
| IC50 | ||||||
Quality Control & MSDS
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Chemical structure
Related Biological Data
Related Biological Data
