T2859

Tamoxifeno

powder, suitable for cell culture, BioReagent

• Sinónimos: (Z)-1-(p-Dimetilaminoetoxifenil)-1,2-difenil-1-buteno, trans-2-[4-(1,2-Difenil-1-butenil)fenoxi]-N,N-dimetiletilamina
• Fórmula lineal: C₆H₅C(C₂H₅)=C(C₆H₅)C₆H₄OCH₂CH₂N(CH₃)₂
• Número de CAS: 10540-29-1
• Peso molecular: 371.51
• MDL number: MFCD00010454
• UNSPSC Code: 12352207
• NACRES: NA.76

Propiedades

• product name: Tamoxifeno, powder, Suitable for cell culture
• Quality Level: 200
• 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
• 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

Descripción

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

Inhibidor de la proteína cinasa C. Induce apoptosis en las líneas celulares de glioma maligno humano. El tamoxifeno y su metabolito el 4-hidroxitamoxifeno son modificadores selectivos de la respuesta a los estrógenos (SERM) que actúan como antagonistas de los estrógenos en las glándulas mamarias. Bloquea la producción del VEGF estimulada por estradiol en las células tumorales de mama.

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 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.

Información de seguridad

• 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
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable