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(Z)-4-Hydroxytamoxifen Sale

(Synonyms: 4-羟基他莫昔芬; (Z)-4-Hydroxytamoxifen; trans-4-Hydroxytamoxifen; (Z)-Afimoxifene) 目录号 : GC16372

4-羟基他莫昔芬((Z)-4-Hydroxytamoxifen)是雌激素受体的选择性调节剂(SERM),其影响[3H]oestradiol与雌激素受体结合的IC50值为3.3 nM。

(Z)-4-Hydroxytamoxifen Chemical Structure

Cas No.:68047-06-3

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10mM (in 1mL DMSO)
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5mg
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10mg
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25mg
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50mg
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Sample solution is provided at 25 µL, 10mM.

产品文档

Quality Control & SDS

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实验参考方法

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.

产品描述

(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.

4-羟基他莫昔芬((Z)-4-Hydroxytamoxifen)是雌激素受体的选择性调节剂(SERM),其影响[3H]oestradiol与雌激素受体结合的IC50值为3.3 nM[1]。(Z)-4-Hydroxytamoxifen可以减少 CRISPR 介导的基因编辑中的脱靶效应[2]。(Z)-4-Hydroxytamoxifen是他莫昔芬的代谢产物,靶向雌激素受体,特别是在乳腺癌细胞中,在乳腺组织中充当拮抗剂,在子宫内膜等其他组织中充当激动剂。这种双重作用使其成为治疗和化学预防雌激素受体阳性乳腺癌的关键药物[3]。

在体外,(Z)-4-Hydroxytamoxifen (1-100nM)处理未成熟大鼠垂体细胞6天,抑制雌二醇刺激的PRL 合成,比他莫昔芬更有效[4]。 (Z)-4-Hydroxytamoxifen低浓度 (0.01-1.00 nM) 在没有雌二醇的情况下,会显著刺激MCF-7细胞集落形成[5]。

在体内,(Z)-4-Hydroxytamoxifen (0.2、1 、5 µg/d,p.o.) 引起未成熟大鼠子宫湿重出现剂量相关降低现象[1]。(Z)-4-Hydroxytamoxifen(6 µg/0.1 mL/day,s.c.)可有效减轻完整和去腺切除的两性 C57BL/6 J 小鼠中甲基苯丙胺诱导的黑质纹状体多巴胺消耗,且不会改变纹状体中的多巴胺水平[6]。

Chemical Properties

Cas No. 68047-06-3 SDF
别名 4-羟基他莫昔芬; (Z)-4-Hydroxytamoxifen; trans-4-Hydroxytamoxifen; (Z)-Afimoxifene
化学名 (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
分子式 C26H29NO2 分子量 387.51
溶解度 ≥ 38.8mg/mL in DMSO 储存条件 Store at -20°C
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1 mM 2.5806 mL 12.9029 mL 25.8058 mL
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