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4-Hydroxytamoxifen (Synonyms: Afimoxifene, 4-OHT)

Catalog No.GC17803

4-Hydroxytamoxifen (Afimoxifene) is a racemic compound of (Z)-4-Hydroxytamoxifen and (E)-4-Hydroxytamoxifen isomers. 4-Hydroxytamoxifen is an estrogen receptor modulator.

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4-Hydroxytamoxifen Chemical Structure

Cas No.: 68392-35-8

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10mg
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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

Multiple myeloma cell lines

Preparation Method

Multiple myeloma cell lines were treated for 48 hours with vehicle or various concentrations of 4-Hydroxytamoxifen (1-10 μmol/L). Cell cycle analysis was done after propidium iodide staining of ethanol-permeabilized cells.

Reaction Conditions

1-10 μmol/L;for 48 hours

Applications

G1-arrest and apoptosis induction of multiple myeloma cells after 4-Hydroxytamoxifen treatment.

Animal experiment [2]:

Animal models

iCM-Akt1/2, iCM-Gsk3β or iCM-p38 mice aged 3–4 month

Preparation Method

For knockout induction, iCM-Akt1/2, iCM-Gsk3β or iCM-p38 mice aged 3–4 month received 4-Hydroxytamoxifen intraperitoneally (20 mg/kg) for either 5, 7, or 10 consecutive days, respectively, and hearts were excised two weeks after the end of the 4-Hydroxytamoxifen treatment for western blot analysis of protein depletion. In addition, immunohistological stainings were performed of hearts from iCM-Akt1/2KO or WT mice two weeks after 5 day 4-Hydroxytamoxifen treatment.

Dosage form

20 mg/kg; for either 5, 7, or 10 consecutive days

Applications

Cardiomyocyte restricted gene deletion was initiated by intraperitoneal application of 20 mg/kg 4-Hydroxytamoxifen on 5, 7 or 10 consecutive days. Administration of 20 mg/kg 4-Hydroxytamoxifen for five consecutive days resulted in loss of both Akt1 and Akt2 in cardiomyocytes.

References:

[1]. Gauduchon J, et al. 4-Hydroxytamoxifen inhibits proliferation of multiple myeloma cells in vitro through down-regulation of c-Myc, up-regulation of p27Kip1, and modulation of Bcl-2 family members. Clin Cancer Res. 2005 Mar 15;11(6):2345-54.

[2]. Heinen A, et al. 4-hydroxytamoxifen does not deteriorate cardiac function in cardiomyocyte-specific MerCreMer transgenic mice. Basic Res Cardiol. 2021 Feb 5;116(1):8.

Background

4-hydroxytamoxifen is a major metabolite of tamoxifen and selective estrogen receptor antagonist. It potentiated the protective effects of estradiol against the MA-induced nigrostriatal DA depletion.[1] 4-Hydroxytamoxifen has the superoxide anion radical-scavenging activity, the antioxidative characteristics of 4-Hydroxytamoxifen can attenuate the MA-induced dopaminergic toxicity.[4]

In vitro, 4-Hydroxytamoxifen decreased the transcriptional activity of ERRγ by more than 75%, with an EC50 value of 2 μM.[5] In MPNST cells were treated with 8-12 μM 4-Hydroxytamoxifen after 48 hours, there has a concentration-dependent increase in caspase 3-like enzymatic activity. 4-Hydroxytamoxifen also triggers autophagic death in MPNST cells.[2] In vitro study it indicated that 10 or 2 µM 4-hydroxytamoxifen abolished the generation of action potentials and repolarized the membrane potential in rat pancreatic beta-cells stimulated by 16 mM glucose. 4-hydroxytamoxifen impairs beta-cell electrical and secretory activity by inhibiting calcium and anion channel currents.[6]

In vivo experiment it shown that αMHC-MerCreMer mice were treated 20 mg/kg 4-hydroxytamoxifen intraperitoneally for 5 consecutive days, neither cardiac function nor cardiac energetic status in αMHC-MerCreMer mice was disturbed. In addition, the injection of 40 mg/kg 4-hydroxytamoxifen also did not impair cardiac function.[3] In vivo efficacy test it demonstrated that treatment with 6 µg/0.1 mL/day subcutaneously of 4-Hydroxytamoxifen significantly mitigated MA-induced nigrostriatal DA and DOPAC depletions in both male and female mice.[4]

References:
[1].Yu L., et al. (2002a) Ovarian hormones do not attenuate methamphetamine-induced dopaminergic neurotoxicity in mice gonadectomized at 4 weeks postpartum. Neuroendocrinology 75, 282–287.
[2].Kohli L, et al. 4-Hydroxytamoxifen induces autophagic death through K-Ras degradation. Cancer Res. 2013 Jul 15;73(14):4395-405.
[3].Heinen A, et al. 4-hydroxytamoxifen does not deteriorate cardiac function in cardiomyocyte-specific MerCreMer transgenic mice. Basic Res Cardiol. 2021 Feb 5;116(1):8.
[4].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.
[5].Coward P, et al. 4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma. Proc Natl Acad Sci U S A. 2001 Jul 17;98(15):8880-4.
[6].Best L. Inhibition of glucose-induced electrical activity by 4-hydroxytamoxifen in rat pancreatic beta-cells. Cell Signal. 2002 Jan;14(1):69-73.

Chemical Properties

Cas No. 68392-35-8 SDF
Synonyms Afimoxifene, 4-OHT
Chemical Name (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol
Canonical SMILES OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CC)C=C1
Formula C26H29NO2 M.Wt 387.51
Solubility ≥ 42mg/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

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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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Average Rating: 5 ★★★★★ (Based on Reviews and 18 reference(s) in Google Scholar.)

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