(Z)-4-Hydroxytamoxifen - CAS 68047-06-3
Category: Inhibitor
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Molecular Formula:
Molecular Weight:
Estrogen Receptor/ERR
(Z)-4-Hydroxytamoxifen is a metabolite of Tamoxifen and acts as an estrogen receptor antagonist. It exhibits more than 100-fold affinity over Tamoxifen. (Z)-4-Hydroxytamoxifen also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing.
Brife Description:
estrogen receptor antagonist
≥98% by HPLC
White to Off-White Solid
(Z)-4-Hydroxytamoxifen; trans-4-Hydroxytamoxifen; ICI 79280; ICI79280; ICI-79280; 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol; 4-Hydroxytamoxifen; Afimoxifene; Hydroxytamoxifen; 4-Monohydroxytamoxifen; Tamogel
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1.Detection of endocrine active substances in the aquatic environment in southern Taiwan using bioassays and LC-MS/MS.
Chen KY1, Chou PH2. Chemosphere. 2016 Jun;152:214-20. doi: 10.1016/j.chemosphere.2016.02.115. Epub 2016 Mar 10.
Endocrine active substances, including naturally occurring hormones and various synthetic chemicals have received much concern owing to their endocrine disrupting potencies. It is essential to monitor their environmental occurrence since these compounds may pose potential threats to biota and human health. In this study, yeast-based reporter assays were carried out to investigate the presence of (anti-)androgenic, (anti-)estrogenic, and (anti-)thyroid compounds in the aquatic environment in southern Taiwan. Liquid chromatography tandem mass spectrometry (LC-MS/MS) was also used to measure the environmental concentrations of selected endocrine active substances for assessing potential ecological risks and characterizing contributions to the endocrine disrupting activities. Bioassay results showed that anti-androgenic (ND-7489 μg L(-1) flutamide equivalent), estrogenic (ND-347 ng L(-1) 17β-estradiol equivalent), and anti-thyroid activities were detected in the dissolved and particulate phases of river water samples, while anti-estrogenic activities (ND-10 μg L(-1) 4-hydroxytamoxifen equivalent) were less often found.
2.Curcumin suppresses 4-hydroxytamoxifen resistance in breast cancer cells by targeting SLUG/Hexokinase 2 pathway.
Geng C1, Li J1, Ding F2, Wu G1, Yang Q1, Sun Y1, Zhang Z1, Dong T1, Tian X3. Biochem Biophys Res Commun. 2016 Mar 21. pii: S0006-291X(16)30379-5. doi: 10.1016/j.bbrc.2016.03.067. [Epub ahead of print]
Triple negative breast cancer (TNBC) is the hardest breast cancer subtype to treat due to lacking therapeutic target and treatment options. In this study, we found that SLUG expression was much higher in TNBC MDA-MB-231 cells than estrogen receptor alpha (ERα) positive breast cancer MCF7 cells. 4-hydroxytamoxifen (4-OHT) promoted SLUG expression, which was blocked by curcumin. Further investigation showed that SLUG activated the transcription of hexokinase-2 (HK2) by binding to HK2 promoter. SLUG knockdown inhibited HK2 expression and weakened 4-OHT resistance of MDA-MB-231 cells. Conversely, SLUG overexpression elevated HK2 level and increased 4-OHT resistance of MCF7 cells. Combination of curcumin and 4-OHT suppressed SLUG and HK2 expression, leading to mitochondrion-mediated apoptosis. These results suggested SLUG as a potential target and curcumin as a promising natural agent for overcoming 4-OHT resistance of TNBC.
3.Microtubule-stabilizing properties of the avocado-derived toxins (+)-(R)-persin and (+)-(R)-tetrahydropersin in cancer cells and activity of related synthetic analogs.
Field JJ1,2, Kanakkanthara A1,3, Brooke DG4,5, Sinha S1, Pillai SD1, Denny WA5,6, Butt AJ7, Miller JH8. Invest New Drugs. 2016 Mar 12. [Epub ahead of print]
The avocado toxin (+)-R-persin (persin) is active at low micromolar concentrations against breast cancer cells and synergizes with the estrogen receptor modulator 4-hydroxytamoxifen. Previous studies in the estrogen receptor-positive breast cancer cell line MCF-7 indicate that persin acts as a microtubule-stabilizing agent. In the present study, we further characterize the properties of persin and several new synthetic analogues in human ovarian cancer cells. Persin and tetrahydropersin cause G2M cell cycle arrest and increase intracellular microtubule polymerization. One analog (4-nitrophenyl)-deshydroxypersin prevents cell proliferation and blocks cells in G1 of the cell cycle rather than G2M, suggesting an additional mode of action of these compounds independent of microtubules. Persin can synergize with other microtubule-stabilizing agents, and is active against cancer cells that overexpress the P-glycoprotein drug efflux pump. Evidence from Flutax-1 competition experiments suggests that while the persin binding site on β-tubulin overlaps the classical taxoid site where paclitaxel and epothilone bind, persin retains activity in cell lines with single amino acid mutations that affect these other taxoid site ligands.
4.Quaking Regulates Neurofascin 155 Expression for Myelin and Axoglial Junction Maintenance.
Darbelli L1, Vogel G1, Almazan G2, Richard S3. J Neurosci. 2016 Apr 6;36(14):4106-20. doi: 10.1523/JNEUROSCI.3529-15.2016.
RNA binding proteins required for the maintenance of myelin and axoglial junctions are unknown. Herein, we report that deletion of the Quaking (QKI) RNA binding proteins in oligodendrocytes (OLs) usingOlig2-Creresults in mice displaying rapid tremors at postnatal day 10, followed by death at postnatal week 3. Extensive CNS hypomyelination was observed as a result of OL differentiation defects during development. The QKI proteins were also required for adult myelin maintenance, because their ablation usingPLP-CreERTresulted in hindlimb paralysis with immobility at ∼30 d after 4-hydroxytamoxifen injection. Moreover, deterioration of axoglial junctions of the spinal cord was observed and is consistent with a loss of Neurofascin 155 (Nfasc155) isoform that we confirmed as an alternative splice target of the QKI proteins. Our findings define roles for the QKI RNA binding proteins in myelin development and maintenance, as well as in the generation of Nfasc155 to maintain healthy axoglial junctions.
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CAS 68047-06-3 (Z)-4-Hydroxytamoxifen

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