2-Methoxyestradiol (2-MeOE2)

- Overview
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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:
    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
- Properties
  - Categories
    
    Apoptotic, antiproliferative and antiangiogenic agent
    
    Alternative Name
    
    2-methoxy Estradiol; (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
    
    CAS Number
    
    362-07-2
    
    Molecular Formula
    
    C19H26O3
    
    Molecular Weight
    
    302.41
    
    Appearance
    
    A solid
    
    Purity
    
    98.25%
    
    Solubility
    
    insoluble in H2O; ≥15.25 mg/mL in DMSO; ≥24.25 mg/mL in EtOH with ultrasonic
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    O[[email protected]@H]1[[email protected]]2(C)[[email protected]](CC1)([H])[[email protected]@](CCC3=CC(O)=C4OC)([H])[[email protected]](C3=C4)([H])CC2
    
    * For Research Use Only
- Reference
  - 1. 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
    2. 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