(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE
Background- Product Name
- (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
- CS-1512;10058-F4;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
- Formula Weight
- 249.35
- MOL File
- 403811-55-2.mol
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Property
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H317May cause an allergic skin reaction
H319Causes serious eye irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- F3680
- Product name
- 10058-F4
- Purity
- ≥98% (HPLC), solid
- Packaging
- 5mg
- Price
- $88.4
- Updated
- 2025/07/31
- Product number
- 475956
- Product name
- c-Myc Inhibitor
- Packaging
- 10mg
- Price
- $186
- Updated
- 2025/07/31
- Product number
- E0959
- Product name
- 5-(4-Ethylbenzylidene)rhodanine
- Packaging
- 25MG
- Price
- $110
- Updated
- 2025/07/31
- Product number
- 15929
- Product name
- 10058-F4
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $62
- Updated
- 2024/03/01
- Product number
- 15929
- Product name
- 10058-F4
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $104
- Updated
- 2024/03/01
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Chemical Properties,Usage,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
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