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Merck
CN

T2859

泰莫西芬

powder, suitable for cell culture, BioReagent

别名:

(Z)-1-(对二甲基氨基乙氧基苯基)-1,2-二苯基-1-丁烯, (Z)-2-[4-(1,2-二苯基-1-丁烯)苯氧基]-N,N-二甲基乙胺

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关于此项目

线性分子式:
C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
化学文摘社编号:
10540-29-1
分子量:
371.51
NACRES:
NA.76
UNSPSC Code:
12352207
MDL number:
MFCD00010454

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产品名称

泰莫西芬, powder, Suitable for cell culture

InChI key

NKANXQFJJICGDU-QPLCGJKRSA-N

SMILES string

CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3

InChI

1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-

assay

≥99%

form

powder

storage condition

protect from light

mp

97-98 °C (lit.)

solubility

H2O: insoluble <0.1% at 20 °C
chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow
2-propanol: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble
propylene glycol: soluble

antibiotic activity spectrum

neoplastics

mode of action

cell membrane | interferes
enzyme | inhibits

shipped in

ambient

storage temp.

2-8°C

Quality Level

200

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Biochem/physiol Actions

乳腺中的雌激素拮抗剂。阻止乳腺肿瘤细胞中的雌二醇刺激的 VEGF 的产生。蛋白激酶 C 抑制剂。
蛋白激酶 C 抑制剂。诱发人类恶性神经胶质瘤细胞系的细胞凋亡。他莫昔芬及其代谢产物 4-羟基他莫昔芬是选择性雌激素反应调节剂 (SERM)，在乳腺中用作雌激素拮抗剂。阻止乳腺肿瘤细胞中雌二醇刺激的 VEGF 的产生。
Active metabolites of TAM act as estrogen antagonists inmammary glands and block VEGF production in breast cancer cells. TAM is known toinhibit mitochondrial function, causing increased glycolysis and lactateproduction. 4-hydroxytamoxifen treatment of iPSC-CMs increased cellsurvival, decreased beating rate and increased beating velocity.

As an antibiotic, TAM increases membrane permeabilityand is active against Gram-positive and Gram- negative bacterial strains. It actsas both bactericidal and bacteriostatic agent.

Application

Contribution of metabolic effects of TAM in increasing drug resistance was studied in MCF-7 and MCF7-TAM cell lines. 4-hydroxytamoxifen was used to examine calcium influx in human-induced pluripotent stem cell-derived cardiomyocytes (iPSC-CMs) modeled on Duchenne Muscular Dystrophy (DMD).

General description

Tamoxifen (TAM) an antimicrobial agent is also a selective estrogen response modifier (SERM) that is used to prevent and treat breast cancer. It was first introduced by AstraZeneca as effective therapeutic and preventive agent against estrogen-positive breast cancer. As an antibiotic, TAM has shown a direct inhibitory action on the growth of Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) strains, and M. tuberculosis.1 It is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4. TAM is also a protein kinase C inhibitor and an anti-angiogenetic factor.

Preparation Note

Tamoxifen is soluble in chloroform at 50 mg/ml and yields a clear, colorless to faint yellow solution. Stock solutions of tamoxifen can also be prepared in DMSO at 10 mM and are stable when stored at -20° C in the dark. It is also soluble in methanol, ethanol, 2-propanol and propylene glycol. It is practically insoluble in water (solubility is <0.01%, 20° C). Solutions are sensitive to UV light.

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B

存储类别

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000439804
0000439804
0000398612
0000398612
0000398613

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Tamoxifen treatment ameliorates contractile dysfunction of Duchenne muscular dystrophy stem cell-derived cardiomyocytes on bioengineered substrates
Foster Birnbaum, Asuka Eguchi, Gaspard Pardon, Alex C. Y. Chang & Helen M. Blau
NPJ Regenerative medicine null
Automated online monitoring of lactate and pyruvate in tamoxifen resistant MCF-7 cells using sequential-injection capillary electrophoresis with contactless conductivity detection (SI-CE-C4D) and correlation with MCT1 and MCT4 genes expression
Ala A. Alhusban, Lama A. Hamadneh, Aliaa I. Shallan & Ola A. TarawnehORCID Icon
Journal of Liquid Chromatography and Related Technologies (2022)

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