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Chemical Structure| 362-07-2 Chemical Structure| 362-07-2

Structure of 2-Methoxyestradiol
CAS No.: 362-07-2

Chemical Structure| 362-07-2

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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

4.5 *For Research Use Only !

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Product Details of 2-Methoxyestradiol

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

Safety of 2-Methoxyestradiol

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:

Related Pathways of 2-Methoxyestradiol

epigenetics
cytoskeleton

Isoform Comparison

Biological Activity

Target
  • HIF

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

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.31mL

0.66mL

0.33mL

16.53mL

3.31mL

1.65mL

33.07mL

6.61mL

3.31mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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