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E8409 Sigma-Aldrich

EF-24

≥98% (HPLC)

Synonym: (3E,5E)-3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone

  • CAS Number 342808-40-6

  • Empirical Formula (Hill Notation) C19H15F2NO

  • Molecular Weight 311.33

  •  MDL number MFCD08560185

  •  PubChem Substance ID 329799079

  •  NACRES NA.77

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Properties

Related Categories Aerobic Glycolysis (the Warburg Effect), Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Metabolism, Cancer Research,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   yellow
solubility   DMSO: ≥10 mg/mL
storage temp.   −20°C
SMILES string   FC1=C(/C=C2CNC/C(C\2=O)=C\C3=CC=CC=C3F)C=CC=C1
InChI   1S/C19H15F2NO/c20-17-7-3-1-5-13(17)9-15-11-22-12-16(19(15)23)10-14-6-2-4-8-18(14)21/h1-10,22H,11-12H2/b15-9+,16-10+
InChI key   NIVYQYSNRUIFIF-KAVGSWPWSA-N

Description

Application

EF-24 has been used to investigate the physiological effects and molecular targets of curcumin in Dictyostelium discoideum. It has also been used to determine the effects of ethanol extract from Zingiber zerumbet (L.) Smith rhizome (EEZZR) on diabetic retinopathy (DR) in streptozotocin (STZ) diabetic rats.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

EF-24 is a IKK inhibitor and curcumin analog. EF-24 is more potent and bioavailable than curcumin, with 10-fold greater potency in cell death induction. It is also more efficacious in anti-cancer screens and less toxic than Cisplatin. EF-24 inhibits HIF-1alpha posttranscriptional activity and induces microtubule stabilization, in contrast to Curcumin. EF-24 up-regulates PTEN expression via inhibition of ubiquitination. EF-24 induces cell death through direct inhibition of IkappaB kinase (IKK), resulting in suppression in NFκB activity.

EF-24 is a IKK inhibitor and curcumin analog. EF-24 is more potent and bioavailable than curcumin, with 10-fold greater potency in cell death induction. It is also more efficacious in anti-cancer screens and less toxic than Cisplatin. EF-24 inhibits HIF-1α posttranscriptional activity and induces microtubule stabilization, in contrast to Curcumin. EF-24 up-regulates PTEN expression via inhibition of ubiquitination. EF-24 induces cell death through direct inhibition of Iκ B kinase (IKK), resulting in suppression in NFκB activity. EF-24/(3E,5E)-3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone is a curcuminoid, that helps to decrease cisplatin-mediated reactive oxygen species in zebrafish. It is highly bioavailable than curcumin and has the ability to target cancer.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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