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Merck

M6383

Sigma-Aldrich

2-Methoxyestradiol

powder

Synonym(e):

1,3,5(10)-Oestratrien-2,3,17β-triol-2-methylether, 2,3,17β-Trihydroxy-1,3,5(10)-oestratrien-2-methylether, 2-Hydroxyoestradiol-2-methylether, 3,17β-Dihydroxy-2-methoxy-1,3,5(10)-oestratrien

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About This Item

Empirische Formel (Hill-System):
C19H26O3
CAS-Nummer:
Molekulargewicht:
302.41
MDL-Nummer:
UNSPSC-Code:
51111800
PubChem Substanz-ID:
NACRES:
NA.77

Sterilität

non-sterile

Qualitätsniveau

Assay

≥98% (HPLC)
≥98% (TLC)

Form

powder

Farbe

white to faint yellow

mp (Schmelzpunkt)

189-190  °C

Löslichkeit

DMSO: 10 mg/mL
ethanol: 10 mg/mL
H2O: insoluble

Versandbedingung

ambient

Lagertemp.

room temp

SMILES String

OC1=C(C=C(C2=C1)[C@]3([H])[C@](CC2)([H])[C@]4([H])CC[C@H](O)[C@](C)4CC3)OC

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-SSTWWWIQSA-N

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Allgemeine Beschreibung

2-Methoxyestradiol (2-ME) is a metabolite, derived from estradiol. It is usually seen at high levels in the normal follicle.

Anwendung

2-Methoxyestradiol has been used:
  • as hypoxia-inducible factor 1-alpha (HIF-1α) inhibitor to treat microglia to test whether hypoxia leads to cell death
  • to determine the anticancer potential in L-lactate-activated osteosarcoma cells
  • as a reference chemical and angiogenesis inhibitor to assess the performance of in vitro angiogenesis assay

Biochem./physiol. Wirkung

2-Methoxyestradiol (2-ME) is a potent inhibitor of endothelial cell proliferation and angiogenesis.It has little affinity for classical estrogen receptors.
2-Methoxyestradiol plays a key role in the apoptosis of tumor cells. It also participates in microtubule stabilization. It exhibits cardioprotective activity and acts as an anticancer agent.

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

N Klauber et al.
Cancer research, 57(1), 81-86 (1997-01-01)
2-Methoxyestradiol (2-ME), an endogenous estrogen metabolite which disrupts microtubule function, has been shown to inhibit proliferating cells in vitro and suppress certain murine tumors in vivo. In vitro screening has determined that breast cancer cell lines are most sensitive to
Hypoxia Induces autophagic cell death through hypoxia-inducible factor 1alpha in microglia
Yang Z, et al.
Testing, 9(5), e96509-e96509 (2014)
Intra-Laboratory Pre-Validation of a Human Cell Based in vitro Angiogenesis Assay for Testing Angiogenesis Modulators
Sarkanen JR, et al.
Frontiers in Pharmacology, 1 (2011)
Efrat Elis et al.
PLoS pathogens, 8(12), e1003103-e1003103 (2013-01-10)
The p12 protein of the murine leukemia virus (MLV) is a constituent of the pre-integration complex (PIC) but its function in this complex remains unknown. We developed an imaging system to monitor MLV PIC trafficking in live cells. This allowed
2-Methoxyestradiol reverses the pro-carcinogenic effect of L-lactate in osteosarcoma 143B cells
Gorska-PM, et al.
Cancer, Genomics, and Proteomics, 14(6), 483-493 (2017)

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