403811-55-2

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;(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;Albb-009118
• CAS NO: 403811-55-2
• Molecular Formula: C12H11NOS2
• Molecular Weight: 249.36
• Product Categories: Inhibitors
• Mol File: 403811-55-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 387.1°C at 760 mmHg
• Flash Point: 187.9°C
• Appearance: yellow/
• Density: 1.33g/cm³
• Vapor Pressure: 3.39E-06mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: 2-8°C
• Solubility: DMSO: >10mg/mL
• 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.
• CAS DataBase Reference: (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE(403811-55-2)
• EPA Substance Registry System: (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE(403811-55-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 403811-55-2(Hazardous Substances Data)

Usage

Description

(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE is a complex organic compound characterized by its unique molecular structure, which consists of a thiazolidinone ring with a 4-ethylbenzylidene group attached to the 5-position. (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE exhibits a range of biological activities and has potential applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE is used as a c-Myc inhibitor for its ability to induce apoptosis. It effectively disables c-Myc by inhibiting the c-Myc-Max association and function, which is crucial in the growth of fibroblasts in a c-Myc-dependent manner. (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE also downregulates human telomerase reverse transcriptase and enhances chemosensitivity in human hepatocellular carcinoma cells.
Used in Cancer Treatment:
In the field of oncology, (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE is used to induce cell cycle arrest, apoptosis, and myeloid differentiation in human acute myeloid leukemia. Its ability to inhibit the MYCN/Max interaction leads to cell cycle arrest, apoptosis, and neuronal differentiation in MYCN-amplified neuroblastoma cells, making it a promising candidate for targeted cancer therapies.
Used in Drug Delivery Systems:
To improve the bioavailability and therapeutic outcomes of (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE, various drug delivery systems have been developed. These systems employ organic and metallic nanoparticles as carriers for the compound, aiming to enhance its delivery and efficacy against cancer cells. This approach can potentially overcome limitations associated with the compound's solubility and stability, allowing for more effective treatment options in cancer therapy.

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).

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

InChI:InChI=1/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+

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 4748-78-1 4-ethylbenzylaldehyde 

Relevant articles and documents

Gold-Based Pharmacophore Inhibits Intracellular MYC Protein

Direct targeting of intrinsically disordered proteins, including MYC, by small molecules for biomedical applications would resolve a longstanding issue in chemical biology and medicine. Thus, we developed gold-based small-molecule MYC reagents that engage MYC inside cells and modulate MYC transcriptional activity. Lead compounds comprise an affinity ligand and a gold(I) or gold(III) warhead capable of protein chemical modification. Cell-based MYC target engagement studies via CETSA and co-immunoprecipitation reveal specific interaction of compounds with MYC in cells. The lead gold(I) reagent, 1, demonstrates superior cell-killing potential (up to 35-fold) in a MYC-dependent manner when compared to 10058-F4 in cells including the TNBC, MDA-MB-231. Subsequently, 1 suppresses MYC transcription factor activity via functional colorimetric assays, and gene-profiling using whole-cell transcriptomics reveals significant modulation of MYC target genes by 1. These findings point to metal-mediated ligand affinity chemistry (MLAC) based on gold as a promising strategy to develop chemical probes and anticancer therapeutics targeting MYC.