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SML1666

Sigma-Aldrich

4-Hydroxytamoxifen

≥98% (HPLC), solution, Tamoxifen metabolite

Sinonimo/i:

4-OHT, cis/trans-4-Hydroxytamoxifen

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About This Item

Formula empirica (notazione di Hill):
C26H29NO2
Numero CAS:
68392-35-8
Peso molecolare:
387.51
Codice UNSPSC:
12352200
NACRES:
NA.77

product name

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

Origine biologica

synthetic

Livello qualitativo

200

Forma fisica

solution

Concentrazione

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

Condizioni di spedizione

dry ice

Temperatura di conservazione

−20°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-
TXUZVZSFRXZGTL-QPLCGJKRSA-N

Azioni biochim/fisiol

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 sulla preparazione

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.

Avvertenze

Danger

Indicazioni di pericolo

H225,H319,H350,H360FD,H412

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

55.4 °F

Punto d’infiammabilità (°C)

13 °C

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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

Sigma-Aldrich

605913

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

Tamoxifen citrate United States Pharmacopeia (USP) Reference Standard

USP

1643306

Tamoxifen citrate

Tamoxifene analytical standard

Supelco

85256

Tamoxifene

(Z)-Endoxifen ≥98% (HPLC)

Sigma-Aldrich

SML2368

(Z)-Endoxifen

Fulvestrant >98% (HPLC)

Sigma-Aldrich

I4409

Fulvestrant

Bexarotene ≥98% (HPLC)

Sigma-Aldrich

SML0282

Bexarotene

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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iScience, 24(12), 103425-103425 (2021-12-09)
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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