2-Methoxyestradiol

• CAT Number: I003330
• CAS Number: 362-07-2
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.41
• Purity: ≥95%
• Target: Apoptosis Inducers
• Solubility: DMSO: ≥ 36 mg/mL
• Storage: 3 years -20C powder
• IC50: 0.71 uM
• InChI: InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12?,13?,15?,18-,19-/m0/s1
• InChIKey: CQOQDQWUFQDJMK-WRWXEFHESA-N
• SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)OC)O

2-methoxyestradiol (2ME2; NSC-659853) is a natural metabolite of estrogen that is known to inhibit HIF-1 alpha with an IC50 of 0.71 ± 0.11 μM for the inhibition of BPAEC migration.IC50 value:0.71 uMTarget: HIF-1αin vitro: 2-Methoxyestradiol exhibits the inhibitory activity of cellular proliferation in a breast carcinoma cell line MDA-MB-435 and an ovarian carcinoma cell line SK-OV-3 with IC50 of 1.38 μM and 1.79 μM, respectively. Furthermore, 2-Methoxyestradiol also inhibits cellular microtubule depolymerization in rat aortic smooth muscle A-10 cells with EC50 of 7.5 μM [1]. 2-Methoxyestradiol inhibits proliferation of MCF-7 and BM cells with IC50 of 52 μM and 8 μM [2]. A recent study shows that 2-Methoxyestradiol (0.5 μM), blocks TGF-β3-induced expression of collagen (Col) type I(αI), Col III(αI), plasminogen activator inhibitor (PAI) 1, connective tissue growth factor (CTGF), and α-smooth muscle actin (α-SMA). Moreover, 2-Methoxyestradiol ameliorates TGF-β3-induced Smad2/3 phosphorylation and nuclear translocation, and inhibits TGF-β3-induced activation of the PI3K/Akt/mTOR pathway [3].in vivo: In a 9L rat glioma (9L-V6R) rat model, 2-Methoxyestradiol significantly decreases HIF-1 activity and inhibits the tumor growth in a dose-dependent manner by 4-fold reduction for 60 mg/kg/day, and 23-fold reduction for 600 mg/kg/day, respectively [4].

Reference

1:A Comparison of 2-Methoxyestradiol Value in Women with Severe Preeclampsia Versus Normotensive Pregnancy. Wantania J, Attamimi A, Siswishanto R.J Clin Diagn Res. 2017 Mar;11(3):QC35-QC38. doi: 10.7860/JCDR/2017/21516.9603. Epub 2017 Mar 1. PMID: 28511459 Free PMC Article2:2-Methoxyestradiol: A 17β-Estradiol Metabolite With Gender-Independent Therapeutic Potential. Dubey RK.Hypertension. 2017 Jun;69(6):1014-1016. doi: 10.1161/HYPERTENSIONAHA.117.09265. Epub 2017 Apr 17. No abstract available. PMID: 28416586 3:2-Methoxyestradiol Reduces Angiotensin II-Induced Hypertension and Renal Dysfunction in Ovariectomized Female and Intact Male Mice. Pingili AK, Davidge KN, Thirunavukkarasu S, Khan NS, Katsurada A, Majid DSA, Gonzalez FJ, Navar LG, Malik KU.Hypertension. 2017 Jun;69(6):1104-1112. doi: 10.1161/HYPERTENSIONAHA.117.09175. Epub 2017 Apr 17. PMID: 28416584 4:High oral bioavailability of 2-methoxyestradiol in PEG-PLGA micelles-microspheres for cancer therapy. Guo X, Chen C, Liu X, Hou P, Guo X, Ding F, Wang Z, Hu Y, Li Z, Zhang Z.Eur J Pharm Biopharm. 2017 Apr 7. pii: S0939-6411(17)30439-3. doi: 10.1016/j.ejpb.2017.04.003. [Epub ahead of print] PMID: 28396280 5:Efficacy of Intravitreal injection of 2-Methoxyestradiol in regression of neovascularization of a retinopathy of prematurity rat model. Said AM, Zaki RG, Salah Eldin RA, Nasr M, Azab SS, Elzankalony YA.BMC Ophthalmol. 2017 Apr 4;17(1):38. doi: 10.1186/s12886-017-0433-3. PMID: 28376733 Free PMC Article6:2-Methoxyestradiol enhances radiosensitivity in radioresistant melanoma MDA-MB-435R cells by regulating glycolysis via HIF-1α/PDK1 axis. Zhao H, Jiang H, Li Z, Zhuang Y, Liu Y, Zhou S, Xiao Y, Xie C, Zhou F, Zhou Y.Int J Oncol. 2017 May;50(5):1531-1540. doi: 10.3892/ijo.2017.3924. Epub 2017 Mar 22. PMID: 28339028 Free PMC Article7:2-Methoxyestradiol Impacts on Amino Acids-mediated Metabolic Reprogramming in Osteosarcoma Cells by Interaction with NMDA Receptor. Gorska-Ponikowska M, Perricone U, Kuban-Jankowska A, Lo Bosco G, Barone G.J Cell Physiol. 2017 Mar 6. doi: 10.1002/jcp.25888. [Epub ahead of print] PMID: 28262924 8:2-Methoxyestradiol protects against IgG immune complex-induced acute lung injury by blocking NF-κB and CCAAT/enhancer-binding protein β activities. Yan C, Shen Y, Sun Q, Yuan D, Tang H, Gao H.Mol Immunol. 2017 May;85:89-99. doi: 10.1016/j.molimm.2017.02.007. Epub 2017 Feb 20. PMID: 28214650 9:2-Methoxyestradiol protects against ischemia/reperfusion injury in alcoholic fatty liver by enhancing sirtuin 1-mediated autophagy. Cho HI, Seo MJ, Lee SM.Biochem Pharmacol. 2017 May 1;131:40-51. doi: 10.1016/j.bcp.2017.02.008. Epub 2017 Feb 16. PMID: 28213273 10:Inhibition of proliferation and invasion in 2D and 3D models by 2-methoxyestradiol in human melanoma cells. Massaro RR, Faião-Flores F, Rebecca VW, Sandri S, Alves-Fernandes DK, Pennacchi PC, Smalley KSM, Maria-Engler SS.Pharmacol Res. 2017 May;119:242-250. doi: 10.1016/j.phrs.2017.02.013. Epub 2017 Feb 14. PMID: 28212889