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Structure of 2-Methoxyestradiol
CAS No.: 362-07-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2-methoxyestradiol 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.
Synonyms: 2-ME2; NSC-659853; Panzem
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Search for reports by entering the product batch number.
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CAS No. : | 362-07-2 |
Formula : | C19H26O3 |
M.W : | 302.41 |
SMILES Code : | OC(C(OC)=C1)=CC2=C1[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CC2 |
Synonyms : |
2-ME2; NSC-659853; Panzem
|
MDL No. : | MFCD00010489 |
InChI Key : | CQOQDQWUFQDJMK-SSTWWWIQSA-N |
Pubchem ID : | 66414 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H301+H311+H331-H315-H319-H335-H350-H360-H372-H410 |
Precautionary Statements: | P201-P202-P260-P264-P270-P271-P273-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311-P305+P351+P338-P308+P313-P332+P313-P337+P313-P391-P403+P233-P405-P501 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
Target |
|
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
metastatic osteosarcoma 143B cells | 1 nM | 8 h | To compare the effects of physiological (1 nM) and pharmacological (1 μM) concentrations of 2-ME on•NO2 generation, results showed significant increase in•NO2 levels even at physiological concentration. | Redox Biol. 2020 May;32:101522. |
metastatic osteosarcoma 143B cells | 1 μM | 2 h | To investigate the effect of 2-ME on the generation of reactive nitrogen species (RNS) in 143B cells, results showed peak NO release at 2 h and peak ONOO− release at 8 h post-treatment. | Redox Biol. 2020 May;32:101522. |
primary cortical cultures (PCCs) | 10 μM | 16 h | inhibited HIF-1α activation and nuclear translocation, preventing hypoxia-mediated STI-1 production | EMBO Mol Med. 2013 Aug;5(8):1227-46. |
A549 cells (3D spheroid model) | 0.78 μM–200 μM | 48 h | To evaluate the effect of 2-methoxyestradiol on the viability of 3D spheroid A549 cells, results showed that 2-methoxyestradiol significantly reduced the viability of 3D spheroid A549 cells in a dose-dependent manner. | Redox Biol. 2022 Sep;55:102395. |
A549 cells(2D spheroid model) | 0.78 μM–100 μM | 24 h | To evaluate the effect of 2-methoxyestradiol on the viability of A549 cells, results showed that 2-methoxyestradiol significantly reduced the viability of A549 cells in a dose-dependent manner. | Redox Biol. 2022 Sep;55:102395. |
LNCaP cells | 3µM | 2 h | 2-ME 2 significantly reduced FLIP expression. | Clin Cancer Res. 2009 Mar 1;15(5):1601-11. |
PC-3 cells | 3µM | 2 h | 2-ME 2 reduced the levels and promoter activity of FLIP (p=0.001), decreased FLIP binding to Fas or FADD, increased cleavage of caspase-8 and Bid, and induced apoptosis. | Clin Cancer Res. 2009 Mar 1;15(5):1601-11. |
SH-SY5Y cells | 1, 2.5, 4, 5 μM | 48 or 72 h, or 1 to 8 days | 2-ME significantly inhibited the proliferation of SH-SY5Y cells and induced apoptosis. | Cancer Lett. 2011 Dec 27;313(2):201-10. |
SK-N-SH cells | 1, 2.5, 4, 5 μM | 48 or 72 h, or 1 to 8 days | 2-ME significantly inhibited the proliferation of SK-N-SH cells and induced apoptosis. DNA fragmentation and chromatin condensation were observed in the cells treated with 4 μM 2-ME for 72 h. | Cancer Lett. 2011 Dec 27;313(2):201-10. |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
C57BL/6 J male mice | Osteoporosis model | Gavage | 75 mg/kg | Once daily for 4 weeks | To study the improvement of bone-vessel metabolism in aged mice and the damage in young mice by 2-Methoxyestradiol | Stem Cell Res Ther. 2022 Feb 5;13(1):59 |
Mice | Lumbar spine instability (LSI) surgery model | Intraperitoneal injection | 75 mg/kg | Once daily for 2 or 4 weeks | Evaluated the therapeutic effect of 2ME2 on experimental intervertebral disc degeneration, showing that 2ME2 significantly attenuated LSI surgery-induced disc degeneration, reduced HIF1α expression, and decreased EP cartilage ossification | Bone Res. 2022 Jan 5;10(1):2 |
Wistar rats | Cyclosporine A-induced nephrotoxicity model | Oral | 5 mg/kg | Once daily for three weeks | To evaluate the protective effects of 2ME-TPGS micelles against cyclosporine A-induced nephrotoxicity. Results showed that 2ME-TPGS significantly ameliorated the deterioration of renal function markers, attenuated pathological changes in kidney tissues, and exhibited significant anti-fibrotic, antioxidant, anti-inflammatory, and anti-apoptotic effects. | Antioxidants (Basel). 2022 Jul 30;11(8):1499 |
Rats | Cerebral ischemia model | Intraperitoneal injection | 100 mg/kg | Daily for 20 days | Inhibited HIF-1α activity, reducing STI-1 expression post-cerebral ischemia | EMBO Mol Med. 2013 Aug;5(8):1227-46. |
TRAMP mice | TRAMP prostate cancer model | Oral | 50 mg/kg | 25 weeks | 2-ME 2 intervention led to tumor regression in 90% of the animals, significantly reduced prostate seminal vesicle complex (PSVC) weight (p<0.001), and significantly lowered pathological scores (p<0.001). Tumor regression was associated with reduced expression of FLIP and Sp1. | Clin Cancer Res. 2009 Mar 1;15(5):1601-11. |
Mice | Cyp1b1−/− and Cyp1b1+/+ mice | Intraperitoneal injection | 1.5 mg/kg | Every 3rd day for 14 days | 2-Methoxyestradiol reduced angiotensin II-induced increases in systolic blood pressure, water consumption, urine output, and proteinuria, and attenuated end-organ damage. | Hypertension. 2017 Jun;69(6):1104-1112 |
Female mice | CPLA2α+/+/Cyp1b1+/+, cPLA2α−/−/Cyp1b1+/+, and cPLA2α+/+/Cyp1b1−/− | Intraperitoneal injection | 1.5 mg/kg | Every third day for 14 days | 2-Methoxyestradiol ameliorates Ang II-induced hypertension, renal fibrosis, and reactive oxygen species production by inhibiting cPLA2α activity and reducing prostaglandin E2 and thromboxane A2 production. | Hypertension. 2021 Nov;78(5):1368-1381 |
Tags: 2-Methoxyestradiol | 2-ME2 | NSC-659853 | NSC659853 | NSC 659853 | NSC-659853 | 2-MeOE2 | antiproliferative | antiangiogenic | apoptosis | microtubule dynamics | VEGF | G2/M arrest | mitosis | 362-07-2
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P378 | |
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