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SML1666

Sigma-Aldrich

4-Hydroxytamoxifen

≥98% (HPLC), solution, Tamoxifen metabolite

Sinônimo(s):

4-OHT, cis/trans-4-Hydroxytamoxifen

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About This Item

Fórmula empírica (Notação de Hill):
C26H29NO2
Número CAS:
68392-35-8
Peso molecular:
387.51
Código UNSPSC:
12352200
NACRES:
NA.77

Nome do produto

4-Hydroxytamoxifen Ready Made Solution, 5 mg/mL in ethanol: isopropanol (95:5)

fonte biológica

synthetic

Nível de qualidade

200

Formulário

solution

concentração

5 mg/mL in ethanol: isopropanol (95:5)

Condições de expedição

dry ice

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

N(CCOc1ccc(cc1)\C(=C(\CC)/c3ccccc3)\c2ccc(cc2)O)(C)C

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-

chave InChI

TXUZVZSFRXZGTL-QPLCGJKRSA-N

Ações bioquímicas/fisiológicas

4-Hydroxytamoxifen is an active metabolite of Tamoxifen.
4-Hydroxytamoxifen is an active metabolite of Tamoxifen. 4-Hydroxytamoxifen is formed by cytochrome P450 2D6 in human liver and is a potent and selective estrogen receptor antagonist. 4-Hydroxytamoxifen has been used to stimulate LC3 lipidation and to form autophagic vesicles in a superoxide-dependent manner. Tamoxifen and 4-Hydroxytamoxifen markedly induce cytochrome P450 3A4 (a major drug-metabolizing enzyme) in primary cultures of human hepatocytes. 4-Hydroxytamoxifen undergoes a cis-trans (E-Z) isomerization, a process that occurs in all common laboratory solvents.
Trans isoform of 4-hydroxytamoxifen possesses antiestrogenic activity, while the cis 4-hydroxytamoxifen serves as a key agonist for estrogen receptor. 4-Hydroxytamoxifen promotes apoptosis via activation of p38 pathway in breast cancer cell cultures.

Nota de preparo

4-Hydroxytamoxifen is provided in a 13 mM solution. The recommended working concentration is 10-100 μM. Therefore, 4-Hydroxytamoxifen Ready Made Solution should be diluted 1:130 - 1:1,300 in cell culture media.

Palavra indicadora

Danger

Classificações de perigo

Aquatic Chronic 3 - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

55.4 °F

Ponto de fulgor (°C)

13 °C

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
039M4123V
11181115
106M4037V
11160804

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Tamoxifen-(N,N-dimethyl-13C2) 99 atom % 13C

Sigma-Aldrich

605913

Tamoxifen-(N,N-dimethyl-13C2)

Tamoxifeno analytical standard

Supelco

85256

Tamoxifeno

(Z)-Endoxifen ≥98% (HPLC)

Sigma-Aldrich

SML2368

(Z)-Endoxifen

Fulvestrant >98% (HPLC)

Sigma-Aldrich

I4409

Fulvestrant

Activation of the p38 mitogen-activated protein kinase pathway by estrogen or by 4-hydroxytamoxifen is coupled to estrogen receptor-induced apoptosis.
Zhang C C and Shapiro D J
The Journal of Biological Chemistry, 275(1), 479-486 (2000)
Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants.
Sun D, et al.
Breast Cancer Research, 8(4), R50-R50 (2006)
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JCI insight, 6(16) (2021-07-02)
Functional loss of myosin Vb (MYO5B) induces a variety of deficits in intestinal epithelial cell function and causes a congenital diarrheal disorder, microvillus inclusion disease (MVID). The impact of MYO5B loss on differentiated cell lineage choice has not been investigated.
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Gastroenterology, 159(4), 1390-1405 (2020-06-15)
Myosin VB (MYO5B) is an essential trafficking protein for membrane recycling in gastrointestinal epithelial cells. The inactivating mutations of MYO5B cause the congenital diarrheal disease, microvillus inclusion disease (MVID). MYO5B deficiency in mice causes mislocalization of SGLT1 and NHE3, but
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We previously showed stabilization of NIK-induced activation of NF-κB non-canonical signaling suppresses MLL-AF9-induced AML. In the current study, we demonstrate that deletion of NF-κB non-canonical RelB prevents the inhibitory effect of NIK stabilization in MLL-AF9 AML. Mechanistically, RelB suppresses its
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