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(Z)-4-Hydroxytamoxifen (Synonyms: ICI 79280, trans-4-hydroxy Tamoxifen)

Katalog-Nr.GC16372

(Z)-4-Hydroxytamoxifen ist ein Metabolit von Tamoxifen. (Z)-4-Hydroxytamoxifen zeigt eine hÖhere AffinitÄt zum ER als Tamoxifen. (Z)-4-Hydroxytamoxifen induziert eine nicht-apoptotische zytotoxische Wirkung in humanen endometrialen Adenokarzinomzellen.

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(Z)-4-Hydroxytamoxifen Chemische Struktur

Cas No.: 68047-06-3

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10mM (in 1mL DMSO)
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5mg
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Cell experiment [1]:

Cell lines

Immature rat pituitary gland cells

Preparation Method

(Z)4-hydroxytamoxifen (1-100nM) were incubated with medium for 6 days, with a fresh medium change on day3. Assay of the incorporation of [3H]leucine was conducted on day 6,and the results were plotted as the PRL level, calculated as the percentage of total incorporation of [3H]leucine into protein.

Reaction Conditions

1-100 nM;6 days

Applications

(Z)-4-Hydroxytamoxifen inhibited estradiol-stimulated PRL synthesis, which was more potent than tamoxifen.

Animal experiment [2]:

Animal models

C57BL/6J mice

Preparation Method

C57BL/6 J mice. Five weeks after gonadectomy, mice received various doses of (Z)-4-Hydroxytamoxifen(0. 1.5, 3.0,6.0,12.0 µg/0.1 mL sesame oil/day) for 3 days, followed by four cumulative doses of MA (10 mg/kg/dose) at a 2-h interval. Two weeks after the MA treatment, mice were killed for DA determinations.

Dosage form

0. 1.5, 3.0,6.0,12.0 µg/0.1 mL ; s.c.

Applications

(Z)-4-Hydroxytamoxifen (6 µg/0.1 mL sesame oil, once daily subcutaneous injection) effectively attenuates methamphetamine-induced nigrostriatal dopamine depletion in intact and gonadectomized C57BL/6 J mice of both sexes. (Z)-4-Hydroxytamoxifen does not alter dopamine levels in the striatum.

References:

[1] JORDAN V C, KOCH R, LANGAN S, et al. Ligand interaction at the estrogen receptor to program antiestrogen action: a study with nonsteroidal compounds in vitro[J]. Endocrinology, 1988, 122(4): 1449-1454.
[2] Kuo YM, et al. 4-Hydroxytamoxifen attenuates methamphetamine-induced nigrostriatal dopaminergic toxicity in intact and gonadetomized mice. J Neurochem. 2003 Dec;87(6):1436-43.

Background

(Z)-4-Hydroxytamoxifen is a selective estrogen receptor modulator (SERM) that influences the binding of [3H]oestradiol to the estrogen receptor with an IC50 value of 3.3 nM[1]. (Z)-4-Hydroxytamoxifen can reduce off-target effects in CRISPR-mediated gene editing[2]. It is a metabolite of tamoxifen, targeting estrogen receptors, especially in breast cancer cells, acting as an antagonist in breast tissues and as an agonist in other tissues such as the endometrium. This dual action makes it a key drug in the treatment and chemoprevention of estrogen receptor-positive breast cancer[3].

In vitro, (Z)-4-Hydroxytamoxifen (1-100nM) treatment of immature rat pituitary cells for 6 days inhibits estradiol-stimulated PRL synthesis more effectively than tamoxifen[4]. At low concentrations (0.01-1.00 nM) in the absence of estradiol, (Z)-4-Hydroxytamoxifen significantly stimulates the formation of MCF-7 cell colonies[5].

In vivo, (Z)-4-Hydroxytamoxifen (0.2, 1, 5 µg/d, p.o.) causes a dose-dependent decrease in wet weight of the uterus in immature rats[1]. (Z)-4-Hydroxytamoxifen (6 µg/0.1 mL/day, s.c.) effectively reduces methamphetamine-induced depletion of striatal dopamine in both intact and adrenalectomized male and female C57BL/6J mice without altering dopamine levels in the striatum[6].

References:
[1] Jordan VC, et al. A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. J Endocrinol. 1977 Nov;75(2):305-16.
[2] Davis KM, et al. Small molecule-triggered Cas9 protein with improved genome-editing specificity. Nat Chem Biol. 2015 May;11(5):316-8.
[3]Shagufta,Irshad,Ahmad.Tamoxifen a pioneering drug: An update on the therapeutic potential of tamoxifen derivatives[J].European Journal of Medicinal Chemistry: Chimie Therapeutique, 2018, 143:515-531.
[4] JORDAN V C, KOCH R, LANGAN S, et al. Ligand interaction at the estrogen receptor to program antiestrogen action: a study with nonsteroidal compounds in vitro[J]. Endocrinology, 1988, 122(4): 1449-1454.
[5] Defriend D , Anderson E , Bell J ,et al.Effects of 4-hydroxytamoxifen and a novel pure antioestrogen (ICI 182780) on the clonogenic growth of human breast cancer cells in vitro[J].Br J Cancer, 1994, 70(2):204-211.
[6] Kuo YM, et al. 4-Hydroxytamoxifen attenuates methamphetamine-induced nigrostriatal dopaminergic toxicity in intact and gonadetomized mice. J Neurochem. 2003 Dec;87(6):1436-43.

Chemical Properties

Cas No. 68047-06-3 SDF
Überlieferungen ICI 79280, trans-4-hydroxy Tamoxifen
Chemical Name (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
Canonical SMILES OC1=CC=C(C=C1)/C(C(C=C2)=CC=C2OCCN(C)C)=C(C3=CC=CC=C3)\CC
Formula C26H29NO2 M.Wt 387.51
Löslichkeit ≥ 38.8mg/mL in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.5806 mL 12.9029 mL 25.8058 mL
5 mM 0.5161 mL 2.5806 mL 5.1612 mL
10 mM 0.2581 mL 1.2903 mL 2.5806 mL
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