| Identification | Back Directory | [Name]
4E1RCat | [CAS]
328998-25-0 | [Synonyms]
4E1RCat
CS-1228
4-[(3E)-3-[[5-(4-nitrophenyl)furan-2-yl]methylidene]-2-oxo-5-phenylpyrrol-1-yl]benzoic acid
4-[2,3-Dihydro-3-[[5-(4-nitrophenyl)-2-furanyl]methylene]-2-oxo-5-phenyl-1H-pyrrol-1-yl]benzoic acid
Benzoic acid, 4-[2,3-dihydro-3-[[5-(4-nitrophenyl)-2-furanyl]Methylene]-2-oxo-5-phenyl-1H-pyrrol-1-yl]-
4-[(3E)-3-[[5-(4-Nitrophenyl)furan-2-yl]methylidene]-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrol-1-yl]benzoic acid | [Molecular Formula]
C28H18N2O6 | [MDL Number]
MFCD01931282 | [MOL File]
328998-25-0.mol | [Molecular Weight]
478.45 |
| Chemical Properties | Back Directory | [Boiling point ]
764.8±60.0 °C(Predicted) | [density ]
1.423±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥5mg/mL | [form ]
powder | [pka]
4.23±0.10(Predicted) | [color ]
brown to dark brown | [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+ | [InChIKey]
BBQRBOIMSKMFFO-LTGZKZEYSA-N | [SMILES]
OC(=O)c1ccc(cc1)N2C(=O)\C(=C\c3ccc(o3)-c4ccc(cc4)[N+]([O-])=O)C=C2c5ccccc5 |
| Hazard Information | Back Directory | [Description]
4E1RCat is an inhibitor of the eIF4F translation initiation complex that blocks eIF4E:eIF4G and eIF4E:4E-BP1 interactions. It has been shown to prevent the assembly of the eIF4F complex and to inhibit cap-dependent translation with an IC50 value of ~4 μM. 4E1RCat was shown to reverse tumor chemoresistance in a mouse model of lymphoma by sensitizing cells to the proapoptotic action of DNA damage. | [Uses]
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. | [in vivo]
4E1RCat (15 mg/kg, i.p.) affacts chemosensitivity of Pten+/-Eμ-Myc tumors in mice. 4E1RCat (15 mg/kg, i.p.) sensitizes Pten+/-Eμ-Myc and Tsc2+/-Eμ-Myc lymphomas to the cytotoxic effects of doxorubicin (Dxr), and 4E1RCat targets translation in mice[1]. | [IC 50]
eIF4 | [References]
[1] REGINA CENCIC. Reversing chemoresistance by small molecule inhibition of the translation initiation complex eIF4F.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2011, 108 3: 1046-1051. DOI: 10.1073/pnas.1011477108 |
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| Company Name: |
BOC Sciences
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| Tel: |
1-631-485-4226; 16314854226 |
| Website: |
https://www.bocsci.com |
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