T2859

Tamoxifen

powder, suitable for cell culture, BioReagent

• Synonym(e): Tamoxifen, (Z)-1-(p-Dimethylaminethoxyphenyl)-1,2-diphenyl-1-buten, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamin
• Lineare Formel: C₆H₅C(C₂H₅)=C(C₆H₅)C₆H₄OCH₂CH₂N(CH₃)₂
• CAS-Nummer: 10540-29-1
• Molekulargewicht: 371.51
• NACRES: NA.76
• UNSPSC Code: 12352207
• MDL number: MFCD00010454

Eigenschaften

• Produktname: Tamoxifen, powder, Suitable for cell culture
• Quality Segment: 200
• assay: ≥99%
• form: powder
• storage condition: protect from light
• mp: 97-98 °C (lit.)
• solubility: acetone: 1 g, clear, colorless to faintly yellow (1 g/ 30 mL)
• antibiotic activity spectrum: neoplastics
• mode of action: cell membrane | interferes, enzyme | inhibits
• shipped in: ambient
• storage temp.: 2-8°C
• 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-
• InChI key: NKANXQFJJICGDU-QPLCGJKRSA-N

Beschreibung

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.

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).

Biochem/physiol Actions

Proteinkinase C-Inhibitor. Induziert Apoptose in menschlichen malignen Gliomzelllinien. Tamoxifen und sein Metabolit 4-Hydroxytamoxifen sind selektive Östrogenrezeptormodulatoren (SERM), die als Östrogen-Antagonisten in Brustdrüsen wirken. Hemmt die Estradiol-stimulierte VEGF-Produktion in Brustkrebszellen.

Östrogen-Antagonist in der Brustdrüse. Hemmt die Östradiol-stimulierte VEGF-Produktion in Brustkrebszellen. Proteinkinase C-Inhibitor.

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.

Preparation Note

Tamoxifen is soluble in Acetone at 1gr/ 30 ml and yields a clear, colorless to faint yellow solution. Solution is sensitive to UV light.

Sicherheitshinweise

• pictograms: GHS08,GHS09
• signalword: Danger
• hcodes: H350,H360,H410
• pcodes: P202 - P273 - P280 - P308 + P313 - P391 - P405
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B
• Lagerklasse: 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