(Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one
- CAS No.
- 403811-55-2
- Chemical Name:
- (Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one
- Synonyms
- 10058-F4;CS-1512;Albb-009118;ZINC01085340;c-Myc Inhibitor;10058-F4 ，S7153;10058-F4, 10 mM in DMSO;5-(4-Ethylbenzylidene)rhodanine;10058-F4, c-Myc-Max dimerization inhibitor;c-Myc Inhibitor - CAS 403811-55-2 - Calbiochem
- CBNumber:
- CB4820970
- Molecular Formula:
- C12H11NOS2
- Molecular Weight:
- 249.35
- MDL Number:
- MFCD00758517
- MOL File:
- 403811-55-2.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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. |
| InChI | 1S/C12H11NOS2/c1-2-8-3-5-9(6-4-8)7-10-11(14)13-12(15)16-10/h3-7H,2H2,1H3,(H,13,14,15)/b10-7+ |
| InChIKey | SVXDHPADAXBMFB-JXMROGBWSA-N |
| SMILES | CCc1ccc(cc1)\C=C2\SC(=S)NC2=O |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H317-H319 | |||||||||
| Precautionary statements | P280-P302+P352-P305+P351+P338 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Faceshields, Gloves | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36-43 | |||||||||
| Safety Statements | 26-36/37 | |||||||||
| WGK Germany | 3 | |||||||||
| HazardClass | IRRITANT | |||||||||
| HS Code | 2934100090 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Eye Irrit. 2 Skin Sens. 1 |
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| NFPA 704 |
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(Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one price More Price(83)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | F3680 | 10058-F4 ≥98% (HPLC), solid | 403811-55-2 | 5mg | $94.8 | 2026-04-30 | Buy |
| Sigma-Aldrich | 475956 | c-Myc Inhibitor | 403811-55-2 | 10mg | $199 | 2026-04-30 | Buy |
| TCI Chemical | E0959 | 5-(4-Ethylbenzylidene)rhodanine | 403811-55-2 | 25MG | $88 | 2026-04-30 | Buy |
| Cayman Chemical | 15929 | 10058-F4 ≥95% | 403811-55-2 | 5mg | $69 | 2026-04-30 | Buy |
| Cayman Chemical | 15929 | 10058-F4 ≥95% | 403811-55-2 | 10mg | $115 | 2026-04-30 | Buy |
(Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one Chemical Properties, Uses, Production
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
Background
The small-molecule 10058-F4 inhibits c-Myc, a transcriptional regulator involved in cell proliferation, differentiation, and apoptosis. Dysregulation of the oncoprotein c-Myc is common in human cancers. 10058-F4 inhibits transactivation of gene expression by c-Myc-Max heterodimers by disrupting the association between c-Myc and the transcription factor Max. 10058-F4 treatment of acute myeloid leukemia cells inhibited c-Myc expression and induced apoptosis and cell arrest at G0/G1. In a mouse neuroblastoma model, 10058-F4 inhibited transactivation by N-Myc-Max, resulting in cell cycle arrest, apoptosis, and tumor growth reduction. Ovarian cancer cells treated with 10058-F4 displayed reduced cell proliferation and enhanced effects of chemotherapeutic drugs. The 10058-F4 inhibitor likely upregulates FOXO transcription factors and downstream genes involved in ovarian G1 cell cycle arrest, apoptosis, and autophagic cell death. 10058-F4 promoted increased expression of thioredoxin-interacting protein in triple-negative breast cancer drug-resistant cells, which promoted reactive oxygen species synthesis and reversed doxorubicin-induced chemotherapy resistance.
References
[1] XIAOYING YIN. Low molecular weight inhibitors of Myc–Max interaction and function[J]. Oncogene, 2003, 22 40: 6151-6159. DOI:10.1038/sj.onc.1206641
[2] CHE-PIN LIN. Small-molecule c-Myc inhibitor, 10058-F4, inhibits proliferation, downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells.[J]. Anti-Cancer Drugs, 2007, 18 2: 161-170. DOI:10.1097/cad.0b013e3280109424
[3] MING-JER HUANG . A small-molecule c-Myc inhibitor, 10058-F4, induces cell-cycle arrest, apoptosis, and myeloid differentiation of human acute myeloid leukemia[J]. Experimental hematology, 2006, 34 11: Pages 1480-1489. DOI:10.1016/j.exphem.2006.06.019
[4] HANNA ZIRATH. MYC inhibition induces metabolic changes leading to accumulation of lipid droplets in tumor cells.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2013: 10258-10263. DOI:10.1073/pnas.1222404110
(Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shanghai Boyle Chemical Co., Ltd. | sales@boylechem.com | China | 2915 | 55 | |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Chembest Research Laboratories Limited | 021-20908456 | sales@BioChemBest.com | China | 5996 | 61 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| Wuhan Chemwish Technology Co., Ltd | 86-027-67849912 | sales@chemwish.com | China | 35884 | 56 |
| Jinan Trio PharmaTech Co., Ltd. | 0531-88811783 | sales@trio-pharmatech.com | China | 1856 | 62 |
| Dalian Meilun Biotech Co., Ltd. | 0411-62910999 13889544652 | sales@meilune.com | China | 4765 | 58 |
| Haoyuan Chemexpress Co., Ltd. | 021-58950125 | info@chemexpress.com | China | 7545 | 61 |
| TOKYO CHEMICAL INDUSTRY CO., LTD. | 03-36680489 | Sales-JP@TCIchemicals.com | Japan | 28364 | 80 |
| TCI Europe | 320-37350700 | sales@tcieurope.eu | Europe | 23654 | 75 |
