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T2859

Sigma-Aldrich

Tamoxifen

powder, suitable for cell culture, BioReagent

Synonym(e):

Tamoxifen, (Z)-1-(p-Dimethylaminethoxyphenyl)-1,2-diphenyl-1-buten, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamin

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About This Item

Lineare Formel:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
CAS-Nummer:
10540-29-1
Molekulargewicht:
371.51
MDL-Nummer:
MFCD00010454
UNSPSC-Code:
12352207
NACRES:
NA.76

product name

Tamoxifen, powder, Suitable for cell culture

Qualitätsniveau

200

Assay

≥99%

Form

powder

Lagerbedingungen

protect from light

mp (Schmelzpunkt)

97-98 °C (lit.)

Löslichkeit

H2O: insoluble <0.1% at 20 °C
chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
2-propanol: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble
propylene glycol: soluble

Wirkungsspektrum von Antibiotika

neoplastics

Wirkungsweise

cell membrane | interferes
enzyme | inhibits

Versandbedingung

ambient

Lagertemp.

2-8°C

SMILES String

CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3

InChI

1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-

InChIKey

NKANXQFJJICGDU-QPLCGJKRSA-N

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Allgemeine Beschreibung

Tamoxifen (TAM) an antimicrobial agent is also a selective estrogen response modifier (SERM) that is used to prevent and treat breast cancer. It was first introduced by AstraZeneca as effective therapeutic and preventive agent against estrogen-positive breast cancer. As an antibiotic, TAM has shown a direct inhibitory action on the growth of Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) strains, and M. tuberculosis.1 It is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4. TAM is also a protein kinase C inhibitor and an anti-angiogenetic factor.

Anwendung

Contribution of metabolic effects of TAM in increasing drug resistance was studied in MCF-7 and MCF7-TAM cell lines. 4-hydroxytamoxifen was used to examine calcium influx in human-induced pluripotent stem cell-derived cardiomyocytes (iPSC-CMs) modeled on Duchenne Muscular Dystrophy (DMD).

Biochem./physiol. Wirkung

Proteinkinase C-Inhibitor. Induziert Apoptose in menschlichen malignen Gliomzelllinien. Tamoxifen und sein Metabolit 4-Hydroxytamoxifen sind selektive Östrogenrezeptormodulatoren (SERM), die als Östrogen-Antagonisten in Brustdrüsen wirken. Hemmt die Estradiol-stimulierte VEGF-Produktion in Brustkrebszellen.
Active metabolites of TAM act as estrogen antagonists inmammary glands and block VEGF production in breast cancer cells. TAM is known toinhibit mitochondrial function, causing increased glycolysis and lactateproduction. 4-hydroxytamoxifen treatment of iPSC-CMs increased cellsurvival, decreased beating rate and increased beating velocity.

As an antibiotic, TAM increases membrane permeabilityand is active against Gram-positive and Gram- negative bacterial strains. It actsas both bactericidal and bacteriostatic agent.

Angaben zur Herstellung

Tamoxifen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution. Stock solutions of tamoxifen can also be prepared in DMSO at 10 mM and are stable when stored at -20° C in the dark. It is also soluble in methanol, ethanol, 2-propanol and propylene glycol. It is practically insoluble in water (solubility is <0.01%, 20° C). Solutions are sensitive to UV light.

Piktogramme

Health hazardEnvironment
GHS08,GHS09

Signalwort

Danger

Gefahreneinstufungen

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

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