ChemicalBook Product Catalog Biochemical Engineering Inhibitors Angiogenesis HIF inhibitor 2-Methoxyestradiol

2-Methoxyestradiol

Product Name2-Methoxyestradiol
CAS362-07-2
MFC19H26O3
MW302.41
EINECS263-807-9
MOL File362-07-2.mol

Chemical Properties

Melting point	188-190°C
Boiling point	464.4±45.0 °C(Predicted)
Density	1.178±0.06 g/cm3(Predicted)
storage temp.	Inert atmosphere,Room Temperature
solubility	DMSO: 10 mg/mL
form	crystalline
pka	10.29±0.60(Predicted)
color	light yellow
λmax	286nm(EtOH)(lit.)
InChI	InChI=1/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-/s3
InChIKey	CQOQDQWUFQDJMK-SSTWWWIQSA-N
SMILES	C[C@@]12[C@H](CC[C@@]1([H])[C@]1([H])CCC3C=C(O)C(OC)=CC=3[C@@]1([H])CC2)O \|&1:1,2,5,7,20,r\|
CAS DataBase Reference	362-07-2(CAS DataBase Reference)

Safety Information

Hazard Codes	T,Xi,N
Risk Statements	23/24/25-36/37/38-48-61-60-46-45-51/53
Safety Statements	22-26-36/37/39-45-53-36-61
RIDADR	UN 3077 9/PG 3
WGK Germany	3
RTECS	KG7537500
HS Code	2937.23.5050
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 Carc. 1B Eye Irrit. 2 Repr. 1B Skin Irrit. 2 STOT RE 1 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

2-Methoxyestradiol depolymerizes microtubules and blocks HIF-1α nuclear accumulation and HIF-transcriptional activity. Phase 2.

Uses

A natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. Binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly

Uses

2-Methoxy 17β-Estradiol is a natural metabolite of 17β-Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. 2-Methoxy 17β-Estradiol binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule assembly and function.

Uses

2-Methoxyestradiol is a tubulin polymerization inhibitor and also decreases HIF-1 activity.

Uses

A natural metabolite of 17Estradiol which is devoid of estrogenic activity. Inhibits cell proliferation and angiogenesis. Binds to the colchicine binding site of tubulin, and has been suggested to function as a natural regulator of microtubule a

Definition

ChEBI: A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.

Biological Activity

Apoptotic, antiproliferative and antiangiogenic agent, in vitro and in vivo ; acts via an estrogen receptor-independent mechanism. Induces p53-induced apoptosis via two pathways: activation of p38 and NF- κ B; and activation of JNK and AP-1 leading to Bcl-2 phosphorylation. Also upregulates death receptor 5 and binds to tubulin, inhibiting its assembly.

in vivo

To investigate the effect of 2-Methoxyestradiol (2-ME2) on uveitis development, C57BL/6 mice are randomly assigned into two groups and immunized with IRBP peptide. 2ME2 group starts 2-Methoxyestradiol (15 mg/kg) intraperitoneally from day 0 to day 13 while control group is given with vehicle. The disease score of 2-Methoxyestradiol (2ME2) group is 0.30±0.30, significantly lower than that of control group 2.09±0.28 (p<0.05), each group containing 5 mice^[3].
Treatment with 2-Methoxyestradiol (60-600 mg/kg/d) results in a dose-dependent inhibition of tumor growth. The percentage of cells with strong pimonidazole-positive staining (+++) is significantly decreased in the 2-Methoxyestradiol-treated group (36.0% for 60 mg/kg/d and 0% for 200 and 600 mg/kg/d) compare with the vehicle-treated group (86.5%). This may be attributed to the dramatic inhibition of tumor growth in a dose-dependent manner following 2-Methoxyestradiol treatment^[4].

IC 50

Human Endogenous Metabolite

Preparation Products And Raw materials

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