E8409
EF-24
≥98% (HPLC)
Synonym(s):
(3E,5E)-3,5-bis[(2-fluorophenyl)methylene]-4-piperidinone
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About This Item
Empirical Formula (Hill Notation):
C19H15F2NO
CAS Number:
Molecular Weight:
311.33
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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
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.
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.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
Certificates of Analysis (COA)
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The ethanol extract of Zingiber zerumbet rhizomes mitigates vascular lesions in the diabetic retina
Hong T Y, et al.
Vascular Pharmacology, 76(1), 18-27 (2016)
Ebru Alp et al.
Journal of cancer research and therapeutics, 13(2), 346-350 (2017-06-24)
Cancer cells exert differential responses to chemotherapeutics and inhibitors. To the best of our knowledge, a few or no research has been performed until now to determine the effect of EF-24 and RAD001 on MDA-MB-231 breast cancer cells with regard
Alice G Vassiliou et al.
Critical care (London, England), 17(5), R199-R199 (2013-09-14)
Gene expression profiling was performed via DNA microarrays in leukocytes from critically ill trauma patients nonseptic upon admission to the ICU, who subsequently developed either sepsis (n = 2) or severe sepsis and acute respiratory distress syndrome (n = 3).
Curcumin and derivatives function through protein phosphatase 2A and presenilin orthologues in Dictyostelium discoideum
Cocorocchio M, et al.
Disease models & mechanisms, 11(1), dmm032375-dmm032375 (2018)
The curcuminoid, EF-24, reduces cisplatin-mediated reactive oxygen species in zebrafish inner ear auditory and vestibular tissues
Monroe J D, et al.
Journal of Clinical Neuroscience : Official Journal of the Neurosurgical Society of Australasia, 57, 152-156 (2018)
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