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SML0197

Sigma-Aldrich

4E1RCat

≥97% (HPLC)

Synonym(s):

4-[(3E)-3-[[5-(4-nitrophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C28H18N2O6
CAS Number:
328998-25-0
Molecular Weight:
478.45
MDL number:
MFCD01931282
UNSPSC Code:
12352200
PubChem Substance ID:
329825222
NACRES:
NA.77

Quality Level

100

assay

≥97% (HPLC)

form

powder

color

faint brown to dark brown-red

solubility

DMSO: ≥5 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

2-8°C

SMILES string

OC(=O)c1ccc(cc1)N2C(=O)\C(=C\c3ccc(o3)-c4ccc(cc4)[N+]([O-])=O)C=C2c5ccccc5

InChI

1S/C28H18N2O6/c31-27-21(16-24-14-15-26(36-24)19-6-12-23(13-7-19)30(34)35)17-25(18-4-2-1-3-5-18)29(27)22-10-8-20(9-11-22)28(32)33/h1-17H,(H,32,33)/b21-16+

InChI key

BBQRBOIMSKMFFO-LTGZKZEYSA-N

Application

4E1RCat was used to inhibit new protein synthesis in transformed primary chicken embryo fibroblasts.

Biochem/physiol Actions

4E1RCat ilnhibits the eIF4F translation initiation complex by binding to IF4E b and inhibiting the interaction between IF4E:eIF4G (IC50 = 3.2 μM). In in vitro translation experiments using MDA-MB-231 cells, 4E1RCat dose dependently inhibited cap-dependent translation, led to a decrease in polysome and 80S ribosomal subunits and reduced levels of the eIF4F-dependant proteins Mcl-1 and c-Myc.

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.
This compound is featured on the MAPKAPs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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