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Key Documents

E8409

Sigma-Aldrich

EF-24

≥98% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C19H15F2NO
Numero CAS:
Peso molecolare:
311.33
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

yellow

Solubilità

DMSO: ≥10 mg/mL

Temperatura di conservazione

−20°C

Stringa SMILE

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+
NIVYQYSNRUIFIF-KAVGSWPWSA-N

Applicazioni

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.

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3


Certificati d'analisi (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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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
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)
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)
Min Tao et al.
Cell cycle (Georgetown, Tex.), 15(3), 381-393 (2016-01-14)
Previous studies have indicated that inflammatory stimulation represses protein phosphatase 2A (PP2A), a well-known tumor suppressor. However, whether PP2A repression participates in pancreatic cancer progression has not been verified. We used lipopolysaccharide (LPS) and macrophage-conditioned medium (MCM) to establish in

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