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AB141943

(Z)-4-Hydroxytamoxifen, estrogen receptor modulator

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(13 Publications)

MW 387.5 Da, Purity >98%. Potent and selective estrogen receptor antagonist (IC50 = 7 nM). Active metabolite of (Z)-tamoxifen (ab120656) and exhibits higher potency in vitro. Shows antiproliferative effect (IC50 = 27 μM). Induces p21 nuclear localization.

View Alternative Names

Atherosclerosis, susceptibility to, included, DKFZp686N23123, DKFZp781L1617, ER, ER-alpha, ER-beta, ERR B2, ERR G2, ERR a, ERR b, ERR beta-2, ERR gamma-2, ERR-alpha, ERR-beta, ERR1 protein, ERR1_HUMAN, ERR2_HUMAN, ERR3_HUMAN, ERRgamma, ER[a], ER[b], ESR, ESR B, ESR BETA, ESR L2, ESR1_HUMAN, ESR2_HUMAN, ESRA, ESRL 1, ESRR A, ESRRG, ESTR B, Era, Erb, Erb2, Esrrb, Estr, Estra, Estradiol Receptor alpha, Estradiol Receptor beta, Estradiol receptor, Estrogen Receptor 1, Estrogen Receptor 2, Estrogen receptor, Estrogen receptor 1 (alpha), Estrogen receptor 2 (ER beta), Estrogen receptor 2 ER beta, Estrogen receptor alpha, Estrogen receptor beta, Estrogen receptor beta 4, Estrogen receptor related 1, Estrogen receptor related 2, Estrogen receptor-like 1, Estrogen receptor-like 2, Estrogen receptor-related protein 3, Estrogen resistance, included, Estrogen-related receptor alpha, Estrogen-related receptor beta, Estrogen-related receptor gamma, Estrra, Estrrb, FLJ16023, HDL cholesterol, augmented response of, to hormone replacement, included, KIAA0832, Myocardial infarction, susceptibility to, included, NR3A1, NR3A2, NR3B1, NR3B3, Nr3b2, Nuclear receptor ERRB2, Nuclear receptor subfamily 3 group A member 1, Nuclear receptor subfamily 3 group A member 2, Nuclear receptor subfamily 3 group B member 1, Nuclear receptor subfamily 3 group B member 2, Nuclear receptor subfamily 3 group B member 3, OTTHUMP00000017718, OTTHUMP00000017719, Orphan nuclear receptor, RNESTROR, Steroid hormone receptor ERR 2, Steroid hormone receptor ERR1, estrogen nuclear receptor beta variant a, estrogen nuclear receptor beta variant b, estrogen receptor related receptor alpha, hERR1

1 Images
Chemical Structure - (Z)-4-Hydroxytamoxifen, estrogen receptor modulator (AB141943)
  • Chemical Structure

Lab

Chemical Structure - (Z)-4-Hydroxytamoxifen, estrogen receptor modulator (AB141943)

2D chemical structure image of ab141943, (Z)-4-Hydroxytamoxifen, estrogen receptor modulator

Key facts

CAS number

68047-06-3

Purity

>98%

Form

Solid

form

Molecular weight

387.5 Da

Molecular formula

C<sub>2</sub><sub>6</sub>H<sub>2</sub><sub>9</sub>NO<sub>2</sub>

PubChem

449459

Nature

Synthetic

Solubility

Soluble in ethanol to 50 mM

Soluble in DMSO to 100 mM

Biochemical name

4-Hydroxytamoxifen

Biological description

Potent and selective estrogen receptor antagonist (IC50 = 7 nM). Active metabolite of (Z)-tamoxifen (ab120656) and exhibits higher potency in vitro. Shows antiproliferative effect (IC50 = 27 μM). Induces p21 nuclear localization.

Canonical smiles

CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3

Isomeric smiles

CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3

InChi

InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

InChiKey

TXUZVZSFRXZGTL-QPLCGJKRSA-N

IUPAC Name

4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The estrogen receptor family includes Estrogen Receptor (ER) Estrogen Receptor beta (ERβ) and Estrogen Related Receptors alpha beta and gamma (ERRα ERRβ ERRγ). These nuclear receptors function as transcription factors activated by estrogen with ER being extensively studied. ER has two subtypes ERα and ERβ with masses approximately 66 kDa and 59 kDa respectively. These receptors are largely expressed in reproductive tissues but also in the brain bone and cardiovascular system. ERRs related yet distinct from ERs do not actually bind estrogens and function independently of these ligands.
Biological function summary

Estrogen receptors regulate gene expression and play essential roles in various physiological processes. They often form receptor complexes to exert their effects. These receptors impact cell reproduction differentiation and development processes influencing tissue homeostasis. ERα is particularly important in breast tissue affecting growth and function and interacts with co-regulator proteins to mediate estrogen responses. ERRs while sharing structural similarities regulate genes involved in energy metabolism and mitochondrial function.

Pathways

The estrogen receptors participate in the estrogen signaling pathway influencing growth and development in response to hormonal changes. They interact strongly with coactivators and corepressors to modulate gene transcription. MAPK/ERK and PI3K/Akt are notable pathways through which ERs exert effects often involving cross-talk with Growth Factor Receptors. ERRs participate in metabolic reprogramming pathways associating with genes that regulate oxidative phosphorylation. These pathways reveal how receptor actions are integrated and regulated in cellular contexts.

Estrogen receptors are significantly involved in breast cancer and osteoporosis. ERα is often overexpressed in many breast cancer types and serves as a target for compounds like 4-hydroxytamoxifen (4-OHT) a selective estrogen receptor modulator. This interaction inhibits estrogen stimulation of cancer cells. ERRs are implicated in metabolic disorders due to their role in energy homeostasis. For osteoporosis the receptor's influence on bone density and turnover points to key therapeutic targets. In breast cancer the relationship between ERα and proteins like Her2/neu can affect treatment responses and prognosis illustrating the critical role estrogen receptors play in disease mechanisms.
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Product protocols

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Publications (13)

Recent publications for all applications. Explore the full list and refine your search

Acta neuropathologica communications 12:200 PubMed39710754

2024

Adequate post-ischemic reperfusion of the mouse brain requires endothelial NFAT5.

Applications

Unspecified application

Species

Unspecified reactive species

Reiner Kunze,Paul Wacker,Paula Breuer,Emil Nasyrov,Ivan M Kur,Andreas Weigert,Andreas H Wagner,Hugo H Marti,Thomas Korff

Cellular and molecular life sciences : CMLS 81:51 PubMed38252153

2024

Combination of blockade of endothelin signalling and compensation of IGF1 expression protects the retina from degeneration.

Applications

Unspecified application

Species

Unspecified reactive species

Naoya Shigesada,Naoya Shikada,Manabu Shirai,Michinori Toriyama,Fumiaki Higashijima,Kazuhiro Kimura,Toru Kondo,Yasumasa Bessho,Takuma Shinozuka,Noriaki Sasai

Nature communications 14:4991 PubMed37591859

2023

An ATR-PrimPol pathway confers tolerance to oncogenic KRAS-induced and heterochromatin-associated replication stress.

Applications

Unspecified application

Species

Unspecified reactive species

Taichi Igarashi,Marianne Mazevet,Takaaki Yasuhara,Kimiyoshi Yano,Akifumi Mochizuki,Makoto Nishino,Tatsuya Yoshida,Yukihiro Yoshida,Nobuhiko Takamatsu,Akihide Yoshimi,Kouya Shiraishi,Hidehito Horinouchi,Takashi Kohno,Ryuji Hamamoto,Jun Adachi,Lee Zou,Bunsyo Shiotani

Nature neuroscience 26:594-605 PubMed36894654

2023

Neurons in the caudal ventrolateral medulla mediate descending pain control.

Applications

Unspecified application

Species

Unspecified reactive species

Xinglong Gu,Yizhen Z Zhang,John J O'Malley,Caitlynn C De Preter,Mario Penzo,Mark A Hoon

Bio-protocol 12: PubMed36213106

2022

Microscopic Detection of DNA Synthesis in Early Mitosis at Repetitive Sequences in Human Cells.

Applications

Unspecified application

Species

Unspecified reactive species

Kazumasa Yoshida,Riko Ishimoto,Masatoshi Fujita

EMBO reports 22:e48961 PubMed33512764

2021

EVL regulates VEGF receptor-2 internalization and signaling in developmental angiogenesis.

Applications

Unspecified application

Species

Unspecified reactive species

Joana Zink,Maike Frye,Timo Frömel,Claudia Carlantoni,David John,Danny Schreier,Andreas Weigert,Hebatullah Laban,Gabriela Salinas,Heike Stingl,Lea Günther,Rüdiger Popp,Jiong Hu,Benoit Vanhollebeke,Hannes Schmidt,Amparo Acker-Palmer,Thomas Renné,Ingrid Fleming,Peter M Benz

Molecular cell : PubMed33503406

2021

A tamoxifen receptor within a voltage-gated sodium channel.

Applications

Unspecified application

Species

Unspecified reactive species

Altin Sula,David Hollingworth,Leo C T Ng,Megan Larmore,Paul G DeCaen,B A Wallace

Nature 582:253-258 PubMed32523119

2020

Basement membrane remodelling regulates mouse embryogenesis.

Applications

Unspecified application

Species

Unspecified reactive species

Christos Kyprianou,Neophytos Christodoulou,Russell S Hamilton,Wallis Nahaboo,Diana Suarez Boomgaard,Gianluca Amadei,Isabelle Migeotte,Magdalena Zernicka-Goetz

Molecular biology of the cell 31:768-781 PubMed32049584

2020

Integrin-linked kinase regulates melanosome trafficking and melanin transfer in melanocytes.

Applications

Unspecified application

Species

Unspecified reactive species

Melissa Crawford,Nancy Liu,Elahe Mahdipour,Kevin Barr,Bryan Heit,Lina Dagnino

The Journal of investigative dermatology 140:425-434.e10 PubMed31330146

2019

Essential Role for Integrin-Linked Kinase in Melanoblast Colonization of the Skin.

Applications

Unspecified application

Species

Unspecified reactive species

Melissa Crawford,Valerie Leclerc,Kevin Barr,Lina Dagnino
View all publications
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