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E8534

Sigma-Aldrich

E3330

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C21H30O6
CAS Number:
136164-66-4
Molecular Weight:
378.46
MDL number:
MFCD00901331
UNSPSC Code:
12352200
PubChem Substance ID:
329799080
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

red to orange

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

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+

InChI key

AALSSIXXBDPENJ-FYWRMAATSA-N

Application

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

Biochem/physiol Actions

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.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
022M4602V
070M4602V
070M4702
119K4601

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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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