(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: 2024-11-14 20:10:21
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. |
Computed Descriptors for (Z,E)-5-(4-ETHYLBENZYLIDINE)-2-THIOXOTHIAZOLIDIN-4-ONE
New Products
(R)-3-Aminobutanenitrile Hydrochloride 4-Aminotetrahydropyran-4-carbonitrile Hydrochloride 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine SODIUM AAS SOLUTION ZINC AAS SOLUTION BUFFER SOLUTION PH 10.0(BORATE) GOOCH CRUCIBLE SINTERED AQUANIL 5 BERYLLIUM AAS SOLUTION AMOXICILLIN (AMOXYCILLIN) TRIHYDRATE ACICLOVIR AMLODIPINE SODIUM METHYL PARABEN Methylcobalamin (vitamin B12) SODIUM VALPROATE 5-Fluoro-2-iodo-3-methylaniline Ethyl 3-(furan-2-yl)-3-hydroxypropanoate 1-Methyl-6-oxo-1,6-dihydropyridazine-3-carbonitrile 3-Bromo-2-hydroxybenzeneacetic acid 5-Iodo-3-methyl-2-nitropyridine 1-(3-Chloro-2-hydroxyphenyl)-2-propanoneRelated products of tetrahydrofuran
You may like
-
5-(4-Ethylbenzylidene)rhodanine CAS 403811-55-2View Details
403811-55-2 -
10058-F4 CAS 403811-55-2View Details
403811-55-2 -
10058-F4 CAS 403811-55-2View Details
403811-55-2 -
c-Myc Inhibitor CAS 403811-55-2View Details
403811-55-2 -
446292-08-6 (S)-2-{2-Oxo-3-[4-(3-oxo-morpholin-4-yl)-phenyl]-oxazolidin-5-ylmethyl}-isoindole-1,3-dione 99View Details
446292-08-6 -
147403-52-9 > 99View Details
147403-52-9 -
5,6-Dimethoxy-2-(4-piperidinylmethyl)-1-indanone hydrochloride 120013-39-0 > 99.0View Details
120013-39-0 -
718635-93-9 3-(dimethylamino)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one >99%View Details
718635-93-9