4-Hydroxytamoxifen | trans-4-Hydroxytamoxifen;(Z)-Afimoxifene;ICI 79280;4-Monohydroxytamoxifen;(Z)-4-OHT;(Z)-4-Hydroxytamoxifen | 4-羟基三苯氧胺（Z异构体） | ERR

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4-Hydroxytamoxifen/4-羟基他莫昔芬 {[allProObj[0].p_purity_real_show]}

货号：A309666 同义名： 4-羟基三苯氧胺（Z异构体） / trans-4-Hydroxytamoxifen; (Z)-Afimoxifene

4-Hydroxytamoxifen is the active metabolite of tamoxifen and a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer.

4-Hydroxytamoxifen/4-羟基他莫昔芬化学结构
CAS号：68047-06-3

4-Hydroxytamoxifen/4-羟基他莫昔芬 3D分子结构
CAS号：68047-06-3

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4-Hydroxytamoxifen/4-羟基他莫昔芬纯度/质量文件产品仅供科研

货号：A309666 标准纯度： {[allProObj[0].p_purity_real_show]} 产品说明书

批次查询：批次纯度: COA SDS NMR HPLC CNMR LC-MS

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4-Hydroxytamoxifen/4-羟基他莫昔芬生物活性

描述

Estrogen receptors (ERs) play a key role in breast cancer progression. It is reported that 75% of women diagnosed with breast cancer have estrogen and progesterone receptor-positive breast tumors^[3]. 4-Hydroxytamoxifen (Afimoxifene, 4-OH-tamoxifen) is the active metabolite of tamoxifen and a selective estrogen receptor modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. 1 µM of 4-OH-tamoxifen treatment for 1h inhibited LM05-E and MCF-7 cells proliferation, and this effect was related to the PI3K/AKT pathway^[4]. In the MCF-7:5C cells, addition of 4-OH-tamoxifen at an equimolar concentration at early time points almost completely reversed the apoptosis induced by ethoxytriphenylethylene (10^-6 M) after 1 and 2 days of treatment^[5]. In vivo, three daily doses of 4-OH-tamoxifen (6 mg/day) effectively attenuated methamphetamine-induced nigrostriatal dopamine depletions in both sexes of intact and gonadectomized C57BL/6 J mice^[6].

4-Hydroxytamoxifen/4-羟基他莫昔芬细胞研究

细胞系	浓度	检测类型	检测时间	活性说明	数据源
african green monkey Vero cells		Proliferation assay	72 h	Antiproliferative activity against african green monkey Vero cells assessed as inhibition of cell viability after 72 hrs by MTT assay, IC50=15.1 μM	25993269
BT-20 cells		Proliferation assay		Inhibitory activity against proliferation of BT-20 cells in presence of TPE at 10e-5 M concentration	2769681
Calu-1 cells		Function assay	30 mins	Inhibition of PLD1 in human Calu-1 cells assessed as decrease in phosphatidylbutanol-[d9] production after 30 mins by mass spectrometric analysis, IC50=4.8 μM	19136975
DU145 cells		Proliferation assay	48 h	Antiproliferative activity against androgen receptor-deficient human DU145 cells incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50=10.7152 μM	21513275

4-Hydroxytamoxifen/4-羟基他莫昔芬参考文献

[1]Zhong Q, Zhang C, et al. Boronic prodrug of 4-hydroxytamoxifen is more efficacious than tamoxifen with enhanced bioavailability independent of CYP2D6 status. BMC Cancer. 2015 Sep 9;15:625.

[2]Asp ML, Martindale JJ, et al. Direct, differential effects of tamoxifen, 4-hydroxytamoxifen, and raloxifene on cardiac myocyte contractility and calcium handling. PLoS One. 2013 Oct 24;8(10):e78768.

[3]Raffo D, Pontiggia O, Bal de Kier Joffé E, Simian M. Non-genomic actions of estradiol and 4-OH-tamoxifen on murine breast cancer cells. Oncol Rep. 2015 Jan;33(1):439-47. doi: 10.3892/or.2014.3558. Epub 2014 Oct 22. PMID: 25338647.

[5]Maximov PY, Abderrahman B, Fanning SW, Sengupta S, Fan P, Curpan RF, Rincon DMQ, Greenland JA, Rajan SS, Greene GL, Jordan VC. Endoxifen, 4-Hydroxytamoxifen and an Estrogenic Derivative Modulate Estrogen Receptor Complex Mediated Apoptosis in Breast Cancer. Mol Pharmacol. 2018 Aug;94(2):812-822. doi: 10.1124/mol.117.111385. Epub 2018 May 8. PMID: 29739819; PMCID: PMC6022805.

[6]Kuo YM, Chen HH, Shieh CC, Chuang KP, Cherng CG, Yu L. 4-Hydroxytamoxifen attenuates methamphetamine-induced nigrostriatal dopaminergic toxicity in intact and gonadetomized mice. J Neurochem. 2003 Dec;87(6):1436-43. doi: 10.1046/j.1471-4159.2003.02089.x. PMID: 14713299.

4-Hydroxytamoxifen/4-羟基他莫昔芬实验方案

计算器

存储液制备

1mg

5mg

10mg

1 mM

5 mM

10 mM

2.58mL

0.52mL

0.26mL

12.90mL

2.58mL

1.29mL

25.81mL

5.16mL

2.58mL

4-Hydroxytamoxifen/4-羟基他莫昔芬技术信息

CAS号	68047-06-3
分子式	C₂₆H₂₉NO₂
分子量	387.51
SMILES Code	OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CC)C=C1
MDL No.	MFCD00278780

别名	4-羟基三苯氧胺（Z异构体） ;trans-4-Hydroxytamoxifen; (Z)-Afimoxifene; ICI 79280; 4-Monohydroxytamoxifen; (Z)-4-OHT; (Z)-4-Hydroxytamoxifen
运输	蓝冰

存储条件

In solvent -20°C:3-6个月-80°C:12个月

Pure form Sealed in dry, 2-8°C

溶解方案

动物实验：请根据您的动物给药指南选择适当的溶解方案。
以下溶解方案都请先按照体外实验的方式配制澄清的储备液，再依次添加助溶剂：
——为保证实验结果的可靠性，澄清的储备液可以根据储存条件，适当保存；体内实验的工作液，建议现用现配，当天使用；以下溶剂前显示的百分比是指该溶剂在终溶液中的体积占比；如在配制过程中出现沉淀、析出现象，可以通过加热和/或超声的方式助溶

方案一

方案二

细胞研究

细胞系	浓度	检测类型	检测时间	活性说明	数据源

african green monkey Vero cells		Proliferation assay	72 h	Antiproliferative activity against african green monkey Vero cells assessed as inhibition of cell viability after 72 hrs by MTT assay, IC50=15.1 μM	25993269
BT-20 cells		Proliferation assay		Inhibitory activity against proliferation of BT-20 cells in presence of TPE at 10e-5 M concentration	2769681
Calu-1 cells		Function assay	30 mins	Inhibition of PLD1 in human Calu-1 cells assessed as decrease in phosphatidylbutanol-[d9] production after 30 mins by mass spectrometric analysis, IC50=4.8 μM	19136975
DU145 cells		Proliferation assay	48 h	Antiproliferative activity against androgen receptor-deficient human DU145 cells incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50=10.7152 μM	21513275
DU145 cells		Proliferation assay	72 h	Antiproliferative activity against human DU145 cells assessed as inhibition of cell viability after 72 hrs by MTT assay, IC50=15.3 μM	25993269
HEK293 cell		Function assay	30 mins	Inhibition of GFP-tagged human PLD2 expressed in human HEK293 cells assessed as decrease in phosphatidylbutanol-[d9] production after 30 mins by mass spectrometric analysis, IC50=0.044 μM	19136975
HEK293 cells		Function assay		Agonist activity at human estrogen related receptor gamma expressed in HEK293 cells by luciferase reporter gene assay, GI50=1.35 μM	25305688
Ishikawa endometrial cells		Function assay		Antagonist activity as inhibition of 1 nM 17-beta-estradiol stimulated alkaline phosphatase induction in Ishikawa endometrial cells, IC50=0.51 μM	15380208
LNCAP cells		Proliferation assay	48 h	Antiproliferative activity against human LNCAP cells expressing androgen receptor incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50=8.31764 μM	21513275
MCF12A cells		Proliferation assay	48 h	Antiproliferative activity against estrogen receptor-deficient human MCF12A cells incubated with 0.003 nM of estradiol and 0.01 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of 5% fetal bovine serum, GI50=3.31131 μM	21513275
MCF12A cells		Proliferation assay	48 h	Antiproliferative activity against estrogen receptor-deficient human MCF12A cells incubated with 0.06 nM of estradiol and 0.07 nM of testosterone after 48 hrs by sulforhodamine B assay in presence of fetal bovine serum and NuSerum, GI50=3.89045 μM	21513275
MCF7 cells		Proliferation assay		Inhibition of estrogen-stimulated MCF-7 cell proliferation, IC50=0.5 nM	9548817
MCF7 cells		Function assay		Inhibitory concentration against MCF-7 breast tumor cells using MCF-7 assay, IC50=8.5 nM	12825935
MCF7 cells		Proliferation assay	72 h	Antiproliferative activity against estrogen receptor dependent human MCF7 cells after 72 hrs by MTT assay, IC50=0.107 μM	18835176
MCF7 cells		Proliferation assay	24 h	Antiproliferative activity against human MCF7 cells after 24 hrs by MTS assay, IC50=8.5 nM	18272256
MCF7 cells	10 μM	Function assay	6 h	Upregulation of ERalpha protein levels in human MCF7 cells at 10 uM after 6 hrs by Western blot method	24332630
MCF7 cells		Function assay	48 h	Anticancer against human ER-positive MCF7 cells assessed as cell viability after 48 hrs by SRB assay, IC50=9.2 μM	24946145
MCF7 cells	250 to 500 nM	Function assay	5 days	Anticancer against human ER-positive MCF7 cells assessed as inhibition of estradiol-induced cell proliferation at 250 to 500 nM after 5 days	24946145
MCF7 cells		Cytotoxicity assay	48 h	Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay, IC50=13.6 μM	25618595
MCF7:WS8 cells		Function assay		Activation of human ER in human MCF7:WS8 cells expressing estrogen responsive element by luciferase reporter gene assay	20334368
MCF7:WS8 cells		Function assay	48 h	Agonist activity at ER in human MCF7:WS8 cells assessed as GREB1 gene expression at 10'-6 M after 48 hrs by RT-PCR analysis	24805199
MCF-7-2a cells		Function assay		Inhibition of estradiol induced estrogen receptor transcriptional activation in MCF-7-2a cells, IC50=0.007 μM	12672249
MDA-MB-231 cells		Function assay	3 days	Cytostatic activity against human MDA-MB-231 cells after 3 days by microtiter assay	20598555
MDA-MB-231 cells		Proliferation assay	24 h	Antiproliferative activity against human MDA-MB-231 cells after 24 hrs by MTT assay, IC50=10.4 μM	24189055
MDA-MB-231 cells		Function assay	48 h	Anticancer against human ER-positive MDA-MB-231 cells assessed as cell viability after 48 hrs by SRB assay, IC50=5.4 μM	24946145
MDA-MB-231 cells		Function assay	48 h	Anticancer against human ER-negative MDA-MB-231 cells assessed as cell viability after 48 hrs by SRB assay, IC50=6.2 μM	24946145
PC3 cells		Proliferation assay	48 h	Antiproliferative activity against androgen receptor-deficient human PC3 cells incubated with 0.6 nM of estradiol and 0.7 nM of testosterone after 48 hrs by sulforhodamine B assay, GI50=7.58578 μM	21513275
rat GH3 cells		Function assay	48 h	Antagonist activity at ER in rat GH3 cells assessed as inhibition of estradiol-induced prolactin gene expression at 10'-6 M after 48 hrs by RT-PCR analysis	24805199
rat GH3 cells		Function assay	48 h	Antagonist activity at ER in rat GH3 cells assessed as inhibition of estradiol-induced prolactin gene expression at 10'-10 to 10'-6 M after 48 hrs by RT-PCR analysis	24805199
SKOV3 cells		Function assay	48 h	Anticancer against human SKOV3 cells overexpressing P-gp assessed as cell viability after 48 hrs by SRB assay, IC50=7.46 μM	24946145
T47D cells		Cytotoxicity assay	5 days	Cytotoxicity against human T47D cells after 5 days, IC50=0.21 μM	23864928
T47D:C:4:2 cells		Function assay		Estrogenic activity at wild type ER alpha expressed in T47D:C:4:2 cells coexpressing estrogen response element by duel luciferase reporter gene assay	20334368

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