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Merck
모든 사진(5)

주요 문서

H7904

Sigma-Aldrich

(Z)-4-Hydroxytamoxifen

≥98% (HPLC), powder, estrogen receptor modulator

동의어(들):

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

실험식(Hill 표기법):
C26H29NO2
CAS Number:
Molecular Weight:
387.51
MDL number:
UNSPSC 코드:
51111800
PubChem Substance ID:
NACRES:
NA.77

제품명

(Z)-4-Hydroxytamoxifen, ≥98% Z isomer

Quality Level

분석

≥98% (HPLC)

양식

powder

저장 조건

desiccated
protect from light

solubility

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

항생제 활성 스펙트럼

neoplastics

동작 모드

enzyme | inhibits

주관자

AstraZeneca

저장 온도

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-

InChI key

TXUZVZSFRXZGTL-QPLCGJKRSA-N

일반 설명

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.

애플리케이션

(Z)-4-Hydroxytamoxifen has been used:
  • as a media supplement to study the cell viability by WST-1 Assay
  • for inducing deletion of transforming growth factor-β (TGF-β gene in mice
  • to induce Cre recombinase activity in vitro.

특징 및 장점

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

픽토그램

Health hazardExclamation markEnvironment

신호어

Danger

유해 및 위험 성명서

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

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


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이미 열람한 고객

Slide 1 of 4

1 of 4

Decreased expression of Yes-associated protein is associated with outcome in the luminal A breast cancer subgroup and with an impaired tamoxifen response
Lehn S, et al.
BMC Cancer, 14, 119-119 (2014)
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
Microglia-Specific Expression of Olfml3 Is Directly Regulated by Transforming Growth Factor ?1-Induced Smad2 Signaling
Neidert N, et al.
Frontiers in Immunology, 9, 1728-1728 (2018)
Tamoxifen and hydroxytamoxifen as intramembraneous inhibitors of lipid peroxidation. Evidence for peroxyl radical scavenging activity
Cust'odio JBA, et al.
Biochemical Pharmacology, 47, 1989-1998 (1994)
Formulation of anti-miR-21 and 4-hydroxytamoxifen co-loaded biodegradable polymer nanoparticles and their antiproliferative effect on breast cancer cells
Devulapally R, et al.
J. Mol. Pharmacol., 12, 2080-2092 (2015)

문서

Modulation of homology-directed repair (HDR) within the context of CRISPR-genome editing has led to the identification of small molecules that enhance CRISPR-mediated HDR efficiency in various cell types.

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