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136164-66-4

(E)-2-((4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylene)undecanoic acid

CAS: 136164-66-4

Molecular Formula: C21H30O6

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136164-66-4 - Names and Identifiers

Name (E)-2-((4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylene)undecanoic acid
Synonyms E3330
E 3330
E-3330
APX3330
CS-1756
APX 3330
(E)-2-((4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylene)undecanoic acid
(2E)-2-[(4,5-Dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]-undecanoic acid
Undecanoic acid, 2-[(4,5-dimethoxy-2-methyl-3,6-dioxo-1,4-cyclohexadien-1-yl)methylene]-, (2E)-
(2E)-2-[(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylidene]undecanoic acid E3330
CAS 136164-66-4
EINECS 604-604-1

136164-66-4 - Physico-chemical Properties

Molecular FormulaC21H30O6
Molar Mass378.46
Density1.13±0.1 g/cm3(Predicted)
Melting Point56-57 °C
Boling Point542.2±50.0 °C(Predicted)
Solubility DMSO: >20mg/mL
Appearancepowder
Colorred to orange
pKa4.29±0.19(Predicted)
Storage Condition2-8°C
UseE3330 is a potent and selective inhibitor of AP endonuclease 1 redox domain.E3330 significantly reduces the growth of human pancreatic cancer cells in vitro and inhibits pancreatic cancer cell migration. E3330 blocks tnf-α-induced activation of IL-8 production in liver cancer cell lines. E3330 inhibits the growth of tumor endothelium and endothelial progenitor cells: therapeutic implications in tumor angiogenesis.
TargetApe-1, Ref-1
In vitro studyIn vitro, E3330 affects hemangioblast development by inhibiting Ape1 redox activity. E3330 inhibits the growth of human pancreatic cancer cell lines PANC1,XPA1,MIAPACA,BxPC3, and pk9. In PANC1 cells, E3330 also promotes the end of the cell cycle, inhibits the DNA binding activity of HIF-1α and the migration of pancreatic cancer cells. In adhh6 cells, E3330 prevents the functional activity of NF-κB by altering the Subcellular transport of APE1 and by blocking the redox-mediated activation of NF-κB, decreased TNF-α and FAs accumulation induced expression by IL-6 and IL-8.
In vivo studyIn mice with endotoxin-mediated hepatitis, E3330 (300 mg/kg, p.o.) attenuated the increase in plasma tumor necrosis factor activity and protected mice from liver injury. In a rat model, E3330 (100 mg/kg, p.o.) also protects rats from endotoxin and galactose-induced liver injury.

136164-66-4 - Reference

Reference
Show more
1: Cesaratto L, Codarin E, Vascotto C, Leonardi A, Kelley MR, Tiribelli C, Tell G. Specific inhibition of the redox activity of ape1/ref-1 by e3330 blocks tnf-α-induced activation of IL-8 production in liver cancer cell lines. PLoS One. 2013 Aug 15;8(8):e70909. doi: 10.1371/journal.pone.0070909. eCollection 2013. PubMed PMID: 23967134; PubMed Central PMCID: PMC3744539.
2: Kelley MR, Luo M, Reed A, Su D, Delaplane S, Borch RF, Nyland RL 2nd, Gross ML, Georgiadis MM. Functional analysis of novel analogues of E3330 that block the redox signaling activity of the multifunctional AP endonuclease/redox signaling enzyme APE1/Ref-1. Antioxid Redox Signal. 2011 Apr 15;14(8):1387-401. doi: 10.1089/ars.2010.3410. Epub 2011 Jan 4. PubMed PMID: 20874257; PubMed Central PMCID: PMC3061197.
3: Zou GM, Karikari C, Kabe Y, Handa H, Anders RA, Maitra A. The Ape-1/Ref-1 redox antagonist E3330 inhibits the growth of tumor endothelium and endothelial progenitor cells: therapeutic implications in tumor angiogenesis. J Cell Physiol. 2009 Apr;219(1):209-18. doi: 10.1002/jcp.21666. PubMed PMID: 19097035.
4: Zou GM, Maitra A. Small-molecule inhibitor of the AP endonuclease 1/REF-1 E3330 inhibits pancreatic cancer cell growth and migration. Mol Cancer Ther. 2008 Jul;7(7):2012-21. doi: 10.1158/1535-7163.MCT-08-0113. PubMed PMID: 18645011; PubMed Central PMCID: PMC3569736.
5: Saitou Y, Shiraki K, Yamanaka T, Miyashita K, Inoue T, Yamanaka Y, Yamaguchi Y, Enokimura N, Yamamoto N, Itou K, Sugimoto K, Nakano T. Augmentat

136164-66-4 - Preparation solution concentration reference

 1mg5mg10mg
1 mM2.642 ml13.211 ml26.423 ml
5 mM0.528 ml2.642 ml5.285 ml
10 mM0.264 ml1.321 ml2.642 ml
5 mM0.053 ml0.264 ml0.528 ml
Last Update:2024-01-02 23:10:35
136164-66-4
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CAS: 136164-66-4
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Mobile: 18916960931
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Email: product@acmec-e.com
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Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: (E)-2-((4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)methylene)undecanoic acid Visit Supplier Webpage Request for quotation
CAS: 136164-66-4
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