(Z)-4-Hydroxytamoxifen

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Cat.No. 3412 - (Z)-4-Hydroxytamoxifen | C26H29NO2 | CAS No. 68047-06-3
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)
Datasheet
Citations (5)
Reviews (1)
Literature (2)
Pathways (1)

Biological Activity

Estrogen receptor antagonist. Tamoxifen (Cat. No. 0999) metabolite; exhibits greater potency than the parent compound. Chemotherapeutic agent. Also activates intein-linked inactive Cas9, reducing off-target CRISPR-mediated gene editing; system has ~25-fold higher specificity than wtCas9.

Technical Data

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

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.75 100
ethanol 19.38 50

Preparing Stock Solutions

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

Certificate of Analysis / Product Datasheet
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References

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


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

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

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

Ito et al (2017) PTK6 regulates growth and survival of endocrine therapy-resistant ER+ breast cancer cells. NPJ Breast Cancer 3 45 PMID: 29167821


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Reviews for (Z)-4-Hydroxytamoxifen

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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.

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Literature in this Area

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Pathways for (Z)-4-Hydroxytamoxifen

Estrogen

Estrogen Signaling Pathway

Estrogen is a steroid hormone that is responsible for the regulation of growth, differentiation and function of the reproductive system. Estrogen signaling is often dysregulated in breast cancer and osteoporosis.