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Submit Review(Z)-4-Hydroxytamoxifen
Description: Metabolite of tamoxifen (Cat. No. 0999)
Alternative Names: 4-OH-TAM
Chemical Name: 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
Purity: ≥98% (HPLC)
Biological Activity for (Z)-4-Hydroxytamoxifen
(Z)-4-Hydroxytamoxifen is an estrogen receptor antagonist (IC50 = 27 μM). (Z)-4-Hydroxytamoxifen is a Tamoxifen (Cat. No. 0999) metabolite; that exhibits greater potency than the parent compound. (Z)-4-Hydroxytamoxifen also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing; system has ~25-fold higher specificity than wtCas9. (Z)-4-Hydroxytamoxifen binds to voltage-gated sodium channels, near the intracellular gate and inhibits the sodium current by delaying channel recovery from the inactivated state (IC50 values are 297 nM and 2.1 µM for NavM and human Nav, respectively in HEK cells); this inhibition is independent of estrogen receptor modulation. Chemotherapeutic agent.
Technical Data for (Z)-4-Hydroxytamoxifen
| M. Wt | 387.51 |
| Formula | C26H29NO2 |
| Storage | Store at +4°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 68047-06-3 |
| PubChem ID | 449459 |
| InChI Key | TXUZVZSFRXZGTL-QPLCGJKRSA-N |
| Smiles | CC\C(C3=CC=CC=C3)=C(C2=CC=C(OCCN(C)C)C=C2)/C1=CC=C(O)C=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (Z)-4-Hydroxytamoxifen
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 38.75 | 100 | |
| ethanol | 7.75 | 20 |
Preparing Stock Solutions for (Z)-4-Hydroxytamoxifen
The following data is based on the product molecular weight 387.51. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.58 mL | 12.9 mL | 25.81 mL |
| 5 mM | 0.52 mL | 2.58 mL | 5.16 mL |
| 10 mM | 0.26 mL | 1.29 mL | 2.58 mL |
| 50 mM | 0.05 mL | 0.26 mL | 0.52 mL |
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Product Datasheets for (Z)-4-Hydroxytamoxifen
References for (Z)-4-Hydroxytamoxifen
References are publications that support the biological activity of the product.
Jordan et al (1977) A monohydroxylated metabolite of tamox. with potent antioestrogenic activity. J.Endocrinology 75 305 PMID: 591813
Desta et al (2004) Comprehensive evaluation of tamox. sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6. J.Pharm.Exp.Ther. 310 1062 PMID: 15159443
Yu and Forman (2003) Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. J.Org.Chem. 68 9489 PMID: 14629178
Davis et al (2015) Small molecule-triggered Cas9 protein with improved genome-editing specificity. Nat.Chem.Biol. 11 316 PMID: 25848930
Seeger et al (2004) Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm.Metab.Res. 36 277 PMID: 15156405
Sula et al (2021) A tamoxifen receptor within a voltage-gated sodium channel. Mol.Cell. 81 1160 PMID: 33503406
If you know of a relevant reference for (Z)-4-Hydroxytamoxifen, please let us know.
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Keywords: (Z)-4-Hydroxytamoxifen, (Z)-4-Hydroxytamoxifen supplier, estrogen, receptors, antagonists, ER, 4-hydroxy-TAM, antiestrogens, antioestrogens, SERM, selective, modulators, CRISPR, Cas9-intein, 4-OH-TAM, Estrogen, and, Related, Receptors, Reagents, 3412, Tocris Bioscience
5 Citations for (Z)-4-Hydroxytamoxifen
Citations are publications that use Tocris products. Selected citations for (Z)-4-Hydroxytamoxifen include:
Chatterjee et al (2019) Paracrine Crosstalk between Fibroblasts and ER+ Breast Cancer Cells Creates an IL1β-Enriched Niche that Promotes Tumor Growth. iScience 19 388 PMID: 31419632
Ito et al (2017) PTK6 regulates growth and survival of endocrine therapy-resistant ER+ breast cancer cells. NPJ Breast Cancer 3 45 PMID: 29167821
Lee et al (2017) MTA1 is a novel regulator of autophagy that induces TAX resistance in breast cancer cells. Autophagy 14 812 PMID: 29130361
Candelaria et al (2015) Alcohol Regulates Genes that Are Associated with Response to Endocrine Therapy and Attenuates the Actions of tamox. in Breast Cancer Cells. PLoS One 10 e0145061 PMID: 26661278
Zhang et al (2019) The BAF and PRC2 Complex Subunits Dpf2 and Eed Antagonistically Converge on Tbx3 to Control ESC Differentiation. Cell Stem Cell 24 138 PMID: 30609396
Do you know of a great paper that uses (Z)-4-Hydroxytamoxifen from Tocris? Please let us know.
Reviews for (Z)-4-Hydroxytamoxifen
Average Rating: 5 (Based on 1 Review.)
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4-hydroxytamoxifen for TRAPing cells.
By
Anonymous on 05/23/2019
Assay Type: In Vivo
Species: Mouse
used for tamoxifen TRAPing using ERT-cre mice. given 3hrs post behavior. single dose was sufficient for recombination
.5mg/ml dissolved in 1% tween 80 and 2.5% DMSO, injected 5mg/kg i.p.
Pathways for (Z)-4-Hydroxytamoxifen
