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| | (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Basic information |
| Product Name: | (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE | | Synonyms: | (5E)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one;c-Myc Inhibitor;ZINC01085340;CS-1512;(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE;10058-F4;5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone;(5E)-5-(4-ethylbenzylidene)-2-mercapto-1,3-thiazol-4(5H)-one | | CAS: | 403811-55-2 | | MF: | C12H11NOS2 | | MW: | 249.35 | | EINECS: | | | Product Categories: | Inhibitors | | Mol File: | 403811-55-2.mol |  |
| | (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Chemical Properties |
| density | 1.33±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO: >10mg/mL | | pka | 7.72±0.30(Predicted) | | form | Yellow solid | | color | yellow | | Water Solubility | Soluble in DMSO. Soluble in water at concentrations less than 2mg/ml | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. |
| Hazard Codes | Xi | | Risk Statements | 36-43 | | Safety Statements | 26-36/37 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 2934100090 |
| | (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Usage And Synthesis |
| Description | 10058-F4 (403811-55-2) effectively disables c-Myc by inhibiting the c-Myc-Max association and function.It prevents the growth of fibroblasts in a c-Myc-dependent manner. Downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells.10058-F4 induces cell cycle arrest, apoptosis and myeloid differentiation in human acute myeloid leukemia.Inhibits the MYCN/Max interaction leading to cell cycle arrest, apoptosis and neuronal differentiation in MYCN-amplified neuroblastoma cells. | | Uses | A c-Myc inhibitor that induces apoptosis | | Definition | ChEBI: 10058-F4 is a member of the class of thiazolidinones that is 2-sulfanylidene-1,3-thiazolidin-4-one which is substituted at position 5 by a (4-ethylphenyl)methylidene group. It is a cell permeable inhibitor of c-Myc-Max dimerization and exhibits antitumour effects in vivo. It downregulates c-Myc expression and upregulates CDK inhibitors, p21 and p27 resulting in the inhibition of proliferation, induction of apoptosis and cell cycle arrest in G0/G1 phase. It has a role as an apoptosis inducer and an antineoplastic agent. It is a thiazolidinone and an olefinic compound. | | Biochem/physiol Actions | 10058-F4 is a c-Myc inhibitor that induces cell-cycle arrest and apoptosis. 10058-F4 is a cell-permeable thiazolidinone that specificallly inhibits the c-Myc-Max interaction and prevents transactivation of c-Myc target gene expression. 10058-F4 inhibits tumor cell growth in a c-Myc-dependent manner both in vitro and in vivo (64 μM using c-Myc transfected Rat1a fibroblasts). | | storage | Store at +4°C | | References | 1) Yin?et al. (2003),?Low molecular weight inhibitors of Myc-Max interaction and function; Oncogene,?22?6151
2) Lin?et al. (2007),?Small-molecule c-Myc inhibitor, 10058-F4, inhibits proliferation, downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells; Anti-Cancer Drugs,?18161
3) Huang?et al. (2006),?A small-molecule c-Myc inhibitor, 10058-F4, induces cell-cycle arrest, apoptosis, and myeloid differentiation of human acute myeloid leukemia; Exp. Hematol.,?34?1480
4) Zirath?et al. (2013),?MYC inhibition induces metabolic changes leading to accumulation of lipid droplets in tumor cells; Proc. Natl. Acad. Sci. USA,?110?10258 |
| | (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Preparation Products And Raw materials |
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