Tamoxifen
SIGMA/T2859 - powder, Suitable for cell culture
Synonym: Tamoxifen; (Z)
CAS Number: 10540-29-1
Empirical Formula (Hill Notation): C26H29NO
Molecular Weight: 371.51
MDL Number: MFCD00010454
Linear Formula: C6H5C(C2H5)=C(C6H5)C6H4OCH2CH2N(CH3)2
Product Type: Chemical
Tamoxifen T2859 Tamoxifen cytotoxicity was tested on two human breast cancer adenocarcinoma cell lines. The metastatic MCF-7 cell line and the highly invasive MDA -MB -231 cell line. The cells were plated in DMEM, 10%FCS (15,000 cells/ well) in a 96-well plate with increasing amounts of Tamoxifen. The plates were incubated at 37°C, 5% CO2 for 48 h. Viability was quantified using a resazurin-based reagent.
Tamoxifen T2859 Tamoxifen cytotoxicity was tested on two human breast cancer adenocarcinoma cell lines. The metastatic MCF-7 cell line and the highly invasive MDA -MB -231 cell line. The cells were plated in DMEM, 10%FCS (15,000 cells/ well) in a 96-well plate with increasing amounts of Tamoxifen. The plates were incubated at 37°C, 5% CO2 for 48 h. Viability was quantified using a resazurin-based reagent.
| antibiotic activity spectrum | Gram-negative bacteria |
| Gram-positive bacteria | |
| mycobacteria | |
| assay | ≥99% |
| form | powder |
| InChI | 1S/C26H29NO/c1-4-25(21-11 |
| InChI key | NKANXQFJJICGDU-QPLCGJKRSA |
| mode of action | cell membrane | interferes |
| enzyme | inhibits | |
| mp | 97-98 °C (lit.) |
| Quality Level | 200  |
| shipped in | ambient |
| SMILES string | CCC(c1ccccc1)=C(/c2ccccc |
| solubility | 2-propanol: soluble |
| chloroform: soluble 50 mg/mL, clear, colorless to faintly yellow | |
| DMSO: soluble | |
| ethanol: soluble | |
| H2O: insoluble <0.1% at 20 °C | |
| methanol: soluble | |
| propylene glycol: soluble | |
| storage condition | protect from light |
| storage temp. | 2-8°C |
| 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: | 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. |
| Biochem/physiol Actions: | Protein kinase C inhibitor. Induces apoptosis in human malignant glioma cell lines. Tamoxifen and its metabolite 4-hydroxytamoxifen are selective estrogen response modifiers (SERMs) that act as estrogen antagonists in mammary gland. Blocks estradiol-stimulated VEGF production in breast tumor cells. |
| 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. |
| Purity | ≥99% |
| mp | 97-98 °C (lit.) |
| Storage Temp. | 2-8°C |
| UNSPSC | 51101500 |