(Z)-4-Hydroxytamoxifen

Name: ( Z )-4-Hydroxytamoxifen
Brand: Tocris Bioscience
SKU: 3412
Rating: 5 (1 reviews)

Tocris Bioscience a Bio-Techne Brand

Catalog # 3412

Citations (5)

(1)

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Key Product Details

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)
Molecular Weight:	387.51

View Full Technical Details for (Z)-4-Hydroxytamoxifen

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 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.

Select a batch to recalculate based on the batch molecular weight:

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	2.58 mL	12.90 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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References for (Z)-4-Hydroxytamoxifen

References are publications that support the biological activity of the product.

Sula A tamoxifen receptor within a voltage-gated sodium channel. Mol.Cell. 2021 PMID: 33503406
Davis Small molecule-triggered Cas9 protein with improved genome-editing specificity. Nat.Chem.Biol. 2015 PMID: 25848930
Desta Comprehensive evaluation of tamox. sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6. J.Pharm.Exp.Ther. 2004 PMID: 15159443
Seeger Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm.Metab.Res. 2004 PMID: 15156405
Yu and Forman Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator. J.Org.Chem. 2003 PMID: 14629178
Jordan A monohydroxylated metabolite of tamox. with potent antioestrogenic activity. J.Endocrinology 1977 PMID: 591813

Citations for (Z)-4-Hydroxytamoxifen (5)

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Citations are publications that use Bio-Techne 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
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

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Customer Reviews for (Z)-4-Hydroxytamoxifen (1)

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4-hydroxytamoxifen for TRAPing cells

Name: Anonymous

Species: Mouse

Assay Type: In Vivo

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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Product Documents for (Z)-4-Hydroxytamoxifen

COA

Certificate of Analysis

To download a Certificate of Analysis, please select a batch below.