(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE

Synonym(s):10058-F4, ( Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one;10058-F4, (Z,E)-5-(4-Ethylbenzylidine)-2-thioxothiazolidin-4-one;5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone;c-Myc Inhibitor - CAS 403811-55-2 - Calbiochem

CAS NO.：403811-55-2
Empirical Formula: C12H11NOS2
Molecular Weight: 249.35
MDL number: MFCD00758517
SAFETY DATA SHEET (SDS)
Update Date: 2025-01-27 09:38:02

(Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE Structural

What is (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE?

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.

The Uses of (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE

A c-Myc inhibitor that induces apoptosis

What are the applications of Application

10058-F4 is a c-Myc inhibitor and apoptosis inducer

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

Properties of (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE

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.

Safety information for (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H317:Sensitisation, Skin H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.