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F3680

Sigma-Aldrich

10058-F4

≥98% (HPLC), solid

Synonym(s):

5-[(4-Ethylphenyl)methylene]-2-thioxo-4-thiazolidinone

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About This Item

Empirical Formula (Hill Notation):
C12H11NOS2
CAS Number:
403811-55-2
Molecular Weight:
249.35
MDL number:
MFCD00758517
UNSPSC Code:
12352200
PubChem Substance ID:
329799701
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

yellow

solubility

DMSO: >10 mg/mL
H2O: <2 mg/mL

storage temp.

2-8°C

SMILES string

CCc1ccc(cc1)\C=C2\SC(=S)NC2=O

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+

InChI key

SVXDHPADAXBMFB-JXMROGBWSA-N

Application

10058-F4 has been used:
  • as c-Myc inhibitor to treat stromal cells
  • as c-Myc inhibitor to determine the effect of c-Myc inhibition on cardiac progenitor cells (CPC) growth
  • as c-Myc inhibitor to culture T cells
  • to treat C4-2 cells to examine the activity of MST1 promoter luciferase reporter construct

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).

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Overexpression of MYC and EZH2 cooperates to epigenetically silence MST1 expression
Kuser-Abali G, et al.
Epigenetics, 9(4), 634-643 (2014)
Camilla U Persson et al.
Scientific reports, 7(1), 10274-10274 (2017-09-02)
Cultured cancer cells serve as important models for preclinical testing of anti-cancer compounds. However, the optimal conditions for retaining original tumor features during in vitro culturing of cancer cells have not been investigated in detail. Here we show that serum-free
Hypoxic Stress Decreases c-Myc Protein Stability in Cardiac Progenitor Cells Inducing Quiescence and Compromising Their Proliferative and Vasculogenic Potential
Bellio MA, et al.
Scientific reports, 7(1), 9702-9702 (2017)
cMyc-p53 feedback mechanism regulates the dynamics of T lymphocytes in the immune response
Madapura HS, et al.
Cell Cycle, 15(9), 1267-1275 (2016)
Bethany C Prudner et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 25(16), 5122-5134 (2019-05-23)
The response to acute and long-term arginine starvation results in a conditional adaptive metabolic reprogramming that can be harnessed for therapeutic opportunities in ASS1-negative tumors. Here, we investigate the underlying biology of priming ASS1- tumors with arginine deiminase (ADI-PEG20) before
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