T2859

Tamoxifene

powder, suitable for cell culture, BioReagent

• Sinonimo/i: (Z)-1-(p-Dimetilamminoetossifenil)-1,2-difenil-1-butene, trans-2-[4-(1,2-difenil-1-butenil)fenossi]-N,N-dimetiletilammina
• Formula condensata: C₆H₅C(C₂H₅)=C(C₆H₅)C₆H₄OCH₂CH₂N(CH₃)₂
• Numero CAS: 10540-29-1
• Peso molecolare: 371.51
• Numero MDL: MFCD00010454
• Codice UNSPSC: 12352207
• NACRES: NA.76

Proprietà

• product name: Tamoxifene, powder, Suitable for cell culture
• Livello qualitativo: 200
• Saggio: ≥99%
• Forma fisica: powder
• Condizioni di stoccaggio: protect from light
• Punto di fusione: 97-98 °C (lit.)
• Solubilità: 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
• Spettro attività antibiotica: neoplastics
• Modalità d’azione: cell membrane | interferes; enzyme | inhibits
• Condizioni di spedizione: ambient
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: 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-; NKANXQFJJICGDU-QPLCGJKRSA-N

Descrizione

Descrizione generale

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.

Applicazioni

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).

Azioni biochim/fisiol

Inibitore della protein-chinasi C Induce l′apoptosi in cellule di glioma maligno umano. Il tamoxifene e il suo metabolita 4-idrossitamoxifene sono modificatori selettivi della risposta agli estrogeni (SERM) che agiscono come antagonisti degli estrogeni nella ghiandola mammaria. Blocca la produzione di VEGF stimolata dall'estradiolo nelle cellule di cancro al seno.

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.

Nota sulla preparazione

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.

Informazioni sulla sicurezza

• Pittogrammi: GHS08,GHS09
• Avvertenze: Danger
• Indicazioni di pericolo: H350,H360,H410
• Consigli di prudenza: P202 - P273 - P280 - P308 + P313 - P391 - P405
• Classi di pericolo: Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable