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E8534

Sigma-Aldrich

E3330

≥98% (HPLC)

Synonyme(s) :

(2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]-undecanoic acid

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About This Item

Formule empirique (notation de Hill):
C21H30O6
Numéro CAS:
136164-66-4
Poids moléculaire :
378.46
Numéro MDL:
MFCD00901331
Code UNSPSC :
12352200
ID de substance PubChem :
329799080
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

red to orange

Solubilité

DMSO: >20 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

CCCCCCCCC\C(=C/C1=C(C)C(=O)C(OC)=C(OC)C1=O)C(O)=O

InChI

1S/C21H30O6/c1-5-6-7-8-9-10-11-12-15(21(24)25)13-16-14(2)17(22)19(26-3)20(27-4)18(16)23/h13H,5-12H2,1-4H3,(H,24,25)/b15-13+

Clé InChI

AALSSIXXBDPENJ-FYWRMAATSA-N

Application

E3330 has been used in the inhibition of endothelial cancer cells and apurinic/apyrimidinic endodeoxyribonuclease 1 (APEX1).

Actions biochimiques/physiologiques

E3330 is a specific inhibitor of AP endonuclease 1 redox domain. E3330 inhibits APE-1 regulation of transcription factors, but does not affect Ape1 DNA repair activity. AP endonuclease 1 (APE1; also known as REF-1) is a multifunctional protein with dual functions in DNA repair and redox regulation of transcription factors. It is involved in apurinic/apyrimidinic endonuclease DNA base excision repair activity, in proofreading exonuclease activity, and in modulating DNA binding activity of several transcription factors including NF-κB, Egr-1, p53, AP-1, CREB, HIF-α, and members of the Pax family. APE1 is overexpressed in several human cancers, and disruption of APE1 function has detrimental effects on cancer cell viability. E3330 significantly reduces the growth of human pancreatic cancer cells in vitro and inhibits pancreatic cancer cell migration.

Mentions de danger

H413

Conseils de prudence

P273 - P501

Classification des risques

Aquatic Chronic 4

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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M Hiramoto et al.
Journal of immunology (Baltimore, Md. : 1950), 160(2), 810-819 (1998-04-29)
The activation of NF-kappa B consists of at least three steps: degradation of I kappa B alpha, translocation of NF-kappa B into the nucleus, ai post-translational modification of NF-kappa B (e.g., phosphorylation of p65). In the present study, we found
Society for Endocrinology BES 2011 (2011)
Brittney A Manvilla et al.
Biochemistry, 50(48), 10540-10549 (2011-10-29)
AP endonuclease 1 (APE1) is a multifaceted protein with essential roles in DNA repair and transcriptional regulation. APE1 (ref-1) activates many transcription factors (TF), including AP-1 and NF-κB. While the mechanism of APE1 redox activity remains unknown, it may involve
Mark R Kelley et al.
Antioxidants & redox signaling, 14(8), 1387-1401 (2010-09-30)
APE1 is a multifunctional protein possessing DNA repair and redox activation of transcription factors. Blocking these functions leads to apoptosis, antiangiogenesis, cell-growth inhibition, and other effects, depending on which function is blocked. Because a selective inhibitor of the APE redox
Yukiko Saitou et al.
World journal of gastroenterology, 11(40), 6258-6261 (2006-01-19)
To investigate the reduction of cell viability in human hepatocellular carcinoma (HCC) cell lines induced by inhibition of nuclear factor kappa B (NF kappa B). HLE, SKHep1, and HepG2 were incubated and E3330 was used to compare the stimulation of
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