T2859

Tamoxifeno

powder, suitable for cell culture, BioReagent

• Sinônimo(s): (Z)-1-(p-dimetilaminoetoxifenil)-1,2-difenil-1-buteno, trans-2-[4-(1,2-difenil-1-butenil)fenoxi]-N,N-dimetiletilamina
• Fórmula linear: C₆H₅C(C₂H₅)=C(C₆H₅)C₆H₄OCH₂CH₂N(CH₃)₂
• Número CAS: 10540-29-1
• Peso molecular: 371.51
• Número MDL: MFCD00010454
• Código UNSPSC: 12352207
• NACRES: NA.76

Propriedades

• product name: Tamoxifeno, powder, Suitable for cell culture
• Nível de qualidade: 200
• Ensaio: ≥99%
• forma: powder
• condição de armazenamento: protect from light
• pf: 97-98 °C (lit.)
• solubilidade: 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
• espectro de atividade do antibiótico: neoplastics
• Modo de ação: cell membrane | interferes; enzyme | inhibits
• Condições de expedição: ambient
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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-
• chave InChI: NKANXQFJJICGDU-QPLCGJKRSA-N

Descrição

Descrição geral

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.

Aplicação

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).

Ações bioquímicas/fisiológicas

Inibidor da proteína quinase C. Induz apoptose em linhagens celulares de glioma maligno humano. O tamoxifeno e seu metabólito 4-hidroxitamoxifeno são modificadores seletivos da resposta ao estrogênio (SERMs) que agem como antagonistas de estrogênio na glândula mamária. Ele bloqueia a produção do fator de crescimento endotelial vascular (VEGF) estimulada por estradiol em células tumorais da 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.

Nota de preparo

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.

Informações de segurança

• Pictogramas: GHS08,GHS09
• Palavra indicadora: Danger
• Frases de perigo: H350,H360,H410
• Declarações de precaução: P202 - P273 - P280 - P308 + P313 - P391 - P405
• Classificações de perigo: Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1A - Repr. 1B
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable