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H7904

Sigma-Aldrich

(Z)-4-Hydroxytamoxifen

≥98% Z isomer

Synonym(e):

4OH-Tamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, (Z)-4-OHT, trans-4-Hydroxytamoxifen

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About This Item

Empirische Formel (Hill-System):
C26H29NO2
CAS-Nummer:
68047-06-3
Molekulargewicht:
387.51
MDL-Nummer:
MFCD00278780
UNSPSC-Code:
51111800
PubChem Substanz-ID:
24895814
NACRES:
NA.77

Qualitätsniveau

300

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

desiccated
protect from light

Löslichkeit

methanol: 10 mg/mL
ethanol: 20 mg/mL (with heating)

Wirkungsspektrum von Antibiotika

neoplastics

Wirkungsweise

enzyme | inhibits

Ersteller

AstraZeneca

Lagertemp.

2-8°C

SMILES String

CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3

InChI

1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

InChIKey

TXUZVZSFRXZGTL-QPLCGJKRSA-N

Angaben zum Gen

human ... ESR1(2099) , ESR2(2100) , ESRRG(2104) , IL6(3569)
rat ... Ar(24208) , Esr1(24890) , Esr2(25149)

Allgemeine Beschreibung

4-Hydroxytamoxifen (4-OHT) is a metabolite of the antiestrogen tamoxifen in humans and other mammals. Both the Z (trans) and E (cis) 4-OHT isomers exhibit antiestrogenic properties in immature rats. Studies on the structure-function relationships of fixed ring systems have revealed that the trans isomer is a potent antiestrogen, while the cis isomer is relatively weaker (about 100 times less potent) as an antiestrogen in T47D breast cancer cells in vitro. 4-OHT binds to estrogen receptors (ER) and estrogen-related receptors (ERR), exerting both estrogenic and anti-estrogenic effects. This compound is a cell-permeable, selective estrogen receptor modulator (SERM). Compared to tamoxifen and its other metabolites, 4-OHT demonstrates a higher affinity for binding to estrogen receptors, resulting in 50 to 100-fold greater potency in inhibiting cell proliferation in normal human breast cells and breast cancer cell lines in culture. Moreover, 4-OHT has been found effective in inhibiting the growth of these cells in the absence of estrogen when cell proliferation was induced by insulin or epidermal growth factor.

Anwendung

Anwendungsgebiete von (Z)-4-Hydroxytamoxifen:
  • Als Medienzusatz zur Untersuchung der Zellviabilität durch den WST-1-Test
  • Zur Einleitung der Deletion des Wachstumshormongens TGF-β in Mäusen
  • Zur Einleitung der Cre-Rekombinase-Aktivität in vitro.

Leistungsmerkmale und Vorteile

Diese Verbindung wurde von AstraZeneca entwickelt. Um weitere pharmazeutisch entwickelte Verbindungen und zugelassene Arzneimittel(kandidaten) anzuzeigen, klicken Sie bitte hier.
Dieser Wirkstoff ist auf der Seite Nuclear Receptors (Steroids) im „Handbook of Receptor Classification and Signal Transduction“ aufgeführt. Andere Seiten dieses Handbuchs finden Sie hier.

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Repr. 1B

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, Gloves, type P3 (EN 143) respirator cartridges

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Tamoxifen -citrat (Salz) ≥99%

Sigma-Aldrich

T9262

Tamoxifen -citrat (Salz)

Tamoxifen analytical standard

Supelco

85256

Tamoxifen

Fulvestrant >98% (HPLC)

Sigma-Aldrich

I4409

Fulvestrant

Tamoxifencitrat European Pharmacopoeia (EP) Reference Standard

T0014000

Tamoxifencitrat

Reidun Aesoy et al.
Molecular cancer research : MCR, 6(10), 1630-1638 (2008-10-17)
Tamoxifen, a partial estrogen receptor antagonist, is part of the standard treatment of both primary and advanced breast cancers. However, significant proportions of breast cancers are either de novo resistant or develop tamoxifen resistance during the course of treatment through
Pei-Shan Hou et al.
Nature communications, 10(1), 3581-3581 (2019-08-10)
The bimodal requisite for a genetic program and external stimuli is a key feature of sensory circuit formation. However, the contribution of cell-intrinsic codes to directing sensory-specific circuits remains unknown. Here, we identify the earliest molecular program that preselects projection
Kevin M Davis et al.
Nature chemical biology, 11(5), 316-318 (2015-04-08)
Directly modulating the activity of genome-editing proteins has the potential to increase their specificity by reducing activity following target locus modification. We developed Cas9 nucleases that are activated by the presence of a cell-permeable small molecule by inserting an evolved
Chihiro Ito et al.
Journal of natural products, 69(1), 138-141 (2006-01-31)
Three new isoflavonoids, named millewanins G (1) and H (2) and furowanin B (3), were isolated from the leaves of Millettia pachycarpa. Their structures were elucidated on the basis of spectroscopic analyses. The antiestrogenic activity in the yeast two-hybrid assay
Natalia L Kononenko et al.
Nature communications, 8, 14819-14819 (2017-04-08)
Autophagosomes primarily mediate turnover of cytoplasmic proteins or organelles to provide nutrients and eliminate damaged proteins. In neurons, autophagosomes form in distal axons and are trafficked retrogradely to fuse with lysosomes in the soma. Although defective neuronal autophagy is associated
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