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(Z)-4-HydroxytamoxifenER modulator, potent and selective

(Z)-4-Hydroxytamoxifen

Catalog No. BCC6015
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10mg $186.00 Ship Within 7 Days
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Quality Control of (Z)-4-Hydroxytamoxifen

Chemical structure

(Z)-4-Hydroxytamoxifen

Biological Activity of (Z)-4-Hydroxytamoxifen

Estrogen receptor antagonist. Tamoxifen 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.

(Z)-4-Hydroxytamoxifen Dilution Calculator

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Chemical Properties of (Z)-4-Hydroxytamoxifen

Cas No. 68047-06-3 SDF Download SDF
Synonyms 4-OH-TAM;4-Hydroxytamoxifen; Afimoxifene; Hydroxytamoxifen; Tamogel; 4-Monohydroxytamoxifen
Chemical Name 4-[(1Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]phenol
SMILES CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
Standard InChIKey DODQJNMQWMSYGS-QPLCGJKRSA-N
Standard InChI InChI=1S/C26H29NO2/c1-4-25(20-10-14-23(28)15-11-20)26(21-8-6-5-7-9-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
Formula C26H29NO2 M.Wt 387.51
Solubility Soluble to 100 mM in DMSO and to 50 mM in ethanol
Storage Store at +4°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of (Z)-4-Hydroxytamoxifen

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5806 mL 12.9029 mL 25.8058 mL 51.6116 mL 64.5145 mL
5 mM 0.5161 mL 2.5806 mL 5.1612 mL 10.3223 mL 12.9029 mL
10 mM 0.2581 mL 1.2903 mL 2.5806 mL 5.1612 mL 6.4514 mL
50 mM 0.0516 mL 0.2581 mL 0.5161 mL 1.0322 mL 1.2903 mL
100 mM 0.0258 mL 0.129 mL 0.2581 mL 0.5161 mL 0.6451 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Background on (Z)-4-Hydroxytamoxifen

Estrogen receptors (ER) are members of the superfamily of ligand-modulated nuclear receptors that mediate the actions of steroid hormones, vitamin D, retinoids, and thyroid hormones. ER is activated in vivo when bound by naturally occurring estrogens such as 17α-estradiol. In addition to regulating these physiological processes, estrogen also plays a central role in stimulating breast cancer growth. (Z)-Tamoxifen is a first generation selective ER modulators that is currently approved by the FDA and is widely used to treat estrogen-dependent breast cancers. Its active metabolite, (Z)-4-Hydroxytamoxifen, is a potent estrogen receptor modulator.

In vitro: (Z)-4-hydroxytamoxifen binds to ER with 8-fold higher affinity than tamoxifen. It was found that only the Z isomer has the required antiestrogenic activity; the (E)-4-hydroxytamoxifen has only about 5% of its affinity for the ER [1].

In vivo: The antioestrogenic activities of (Z)-4-hydroxytamoxifen and tamoxifen were determined after oral administration. (Z)-4-hydroxytamoxifen was administered to groups of immature rats which also received s.c. injections of 0-2 μg oestradiol. Both compounds produced a dose-related decrease in uterine wet weight when compared with the oestradiol-treated controls. At a dose of 1 μg/day, the antiuterotrophic effects of (Z)-4-hydroxytamoxifen and tamoxifen were not significantly different but at 5μg/day, (Z)-4-hydroxytamoxifen was more active (P < 0.01). (Z)-4-hydroxytamoxifen therefore appears to retain its potent antioestrogenic activity after oral administration [2].

Clinical trial: Up to now, (Z)-4-Hydroxytamoxifen is still in the preclinical development stage.

Reference:
[1] Donna D.  Yu and Barry M. Forman. Simple and Efficient Production of (Z)-4-Hydroxytamoxifen, a Potent Estrogen Receptor Modulator. J. Org. Chem. 2003, 68, 9489-9491
[2] Jordan VC, Collins MM, Rowsby L, Prestwich G.  A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. J Endocrinol. 1977 Nov;75(2):305-16.

References on (Z)-4-Hydroxytamoxifen

Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator.[Pubmed: 14629178]


A McMurry coupling reaction and selective crystallization were used to develop a simple and efficient two-step synthesis of (Z)-4-hydroxytamoxifen (2a). This compound is an active metabolite of tamoxifen, a selective estrogen receptor (ER) modulator widely used to treat breast cancer. The synthesis employed 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene (1) as a useful building block.

Synthesis of (Z)-4-hydroxytamoxifen and (Z)-2-[4-[1-(p-hydroxyphenyl)-2-phenyl]-1butenyl]phenoxyacetic acid.[Pubmed: 12076167]


The synthesis of (Z)-4-hydroxytamoxifen and (Z)-2-[4-[1-(p-hydroxyphenyl)-2-phenyl]-1-butenyl]phenoxyacetic acid was accomplished using a McMurry reaction as the key step. The perfluorotolyl derivatives of the McMurry products enabled the separation of the minor undesirable geometrical isomer. The methodology proceeds without E,Z isomerization, employs a very mild final debenzylation step compatible with a large array of functional groups, and can be applied to the generation of a variety of 4-hydroxytamoxifen analogues.

Synthesis and sulfatase inhibitory activities of (E)- and (Z)-4-hydroxytamoxifen sulfamates.[Pubmed: 10021916]


We report the development of (E)- and (Z)-4-hydroxytamoxifen sulfamates as estrone sulfatase inhibitors, potential therapeutic agents for the treatment of breast cancer. Both compounds competitively inhibit estrone sulfatase isolated from rat liver with apparent Ki of 35.9 microM for (E)-4-hydroxytamoxifen sulfamate and an apparent Ki of > 500 microM for the (Z) isomer.

New Highly Stereoselective Synthesis of (Z)-4-Hydroxytamoxifen and (Z)-4-Hydroxytoremifene via McMurry Reaction.[Pubmed: 11667248]




Kewords:

(Z)-4-Hydroxytamoxifen,68047-06-3,4-OH-TAM;4-Hydroxytamoxifen; Afimoxifene; Hydroxytamoxifen; Tamogel; 4-Monohydroxytamoxifen,Endocrinology and Hormones,Estrogen/progestogen Receptor, supplier, inhibitor,Antagonist,Blocker,Modulator,Agonist, activators, activates, potent, BioCrick

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