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E8534 Sigma

E3330

≥98% (HPLC)

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

  • CAS Number 136164-66-4

  • Empirical Formula (Hill Notation) C21H30O6

  • Molecular Weight 378.46

  •  MDL number MFCD00901331

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Description

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.

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References

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Small-molecule inhibitor of the AP endonuclease 1/REF-1 E3330 inhibits pancreatic cancer cell growth and migration. Zou, G.M., and Maitra, A. Mol. Cancer Ther. 7, 2012-2021, (2008)

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Ape1 regulates hematopoietic differentiation of embryonic stem cells through its redox functional domain. Zou, G.M., et al. Blood 28, 1917-1922, (2007)

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The DNA base excision repair protein Ape1/Ref1 as a therapeutic and chemopreventive target. Fishel, M.L., and Kelley, M.R. Mol. Aspects Med. 28, 375-395, (2007)

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High-performance affinity beads for identifying drug receptors. Shimizu N, Sugimoto K, Tang J, et al. Nat. Biotechnol. 18(8), 877-81, (2000)

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High-performance affinity beads for identifying anti-NF-kappa B drug receptors. Hiramoto M, Shimizu N, Nishi T, et al. Meth. Enzymol. 353, 81-8, (2002)

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The Ape-1/Ref-1 redox antagonist E3330 inhibits the growth of tumor endothelium and endothelial progenitor cells: therapeutic implications in tumor angiogenesis. Zou GM, Karikari C, Kabe Y, et al. J. Cell Physiol. 219(1), 209-18, (2009)

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Nuclear targeted suppression of NF-kappa B activity by the novel quinone derivative E3330. Hiramoto M, Shimizu N, Sugimoto K, et al. J. Immunol. 160(2), 810-9, (1998)

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Human apurinic/apyrimidinic endonuclease 1 (APE1) has 3' RNA phosphatase and 3' exoribonuclease activities. Chohan M, Mackedenski S, Li WM, et al. J. Mol. Biol. 427(2), 298-311, (2015)

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[Elucidation of pharmacological mechanism of drugs by studying the receptors]. Handa H Jpn. J. Antibiot. 56 Suppl A, 39-46, (2003)

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Role of the multifunctional DNA repair and redox signaling protein Ape1/Ref-1 in cancer and endothelial cells: small-molecule inhibition of the redox function of Ape1. Luo M, Delaplane S, Jiang A, et al. Antioxid. Redox Signal. 10(11), 1853-67, (2008)

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Design and synthesis of novel quinone inhibitors targeted to the redox function of apurinic/apyrimidinic endonuclease 1/redox enhancing factor-1 (Ape1/ref-1). Nyland, R. L.; et al. J. Med. Chem. 53, 1200, (2010)

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APE1/Ref-1 prevents oxidative inactivation of ERK for G1-to-S progression following lead acetate exposure. Wang YT, Tzeng DW, Wang CY, et al. Toxicology 305, 120-9, (2013)

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Functional analysis of novel analogues of E3330 that block the redox signaling activity of the multifunctional AP endonuclease/redox signaling enzyme APE1/Ref-1. Kelley MR, Luo M, Reed A, et al. Antioxid. Redox Signal. 14(8), 1387-401, (2011)

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Knock-in reconstitution studies reveal an unexpected role of Cys-65 in regulating APE1/Ref-1 subcellular trafficking and function. Vascotto C, Bisetto E, Li M, et al. Mol. Biol. Cell 22(20), 3887-901, (2011)

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Inhibition of APE1/Ref-1 redox activity with APX3330 blocks retinal angiogenesis in vitro and in vivo. Jiang A, Gao H, Kelley MR, et al. Vision Res. 51(1), 93-100, (2011)

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Impact of APE1/Ref-1 redox inhibition on pancreatic tumor growth. Fishel ML, Jiang Y, Rajeshkumar NV, et al. Mol. Cancer Ther. 10(9), 1698-708, (2011)

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APE1/Ref-1 regulates STAT3 transcriptional activity and APE1/Ref-1-STAT3 dual-targeting effectively inhibits pancreatic cancer cell survival. Cardoso AA, Jiang Y, Luo M, et al. PLoS ONE 7(10), e47462, (2012)

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Soy isoflavones augment radiation effect by inhibiting APE1/Ref-1 DNA repair activity in non-small cell lung cancer. Singh-Gupta V, Joiner MC, Runyan L, et al. J. Thorac. Oncol. 6(4), 688-98, (2011)

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Characterization of the redox activity and disulfide bond formation in apurinic/apyrimidinic endonuclease. Luo M, Zhang J, He H, et al. Biochemistry 51(2), 695-705, (2012)

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Interactions of apurinic/apyrimidinic endonuclease with a redox inhibitor: evidence for an alternate conformation of the enzyme. Su D, Delaplane S, Luo M, et al. Biochemistry 50(1), 82-92, (2011)

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NMR studies reveal an unexpected binding site for a redox inhibitor of AP endonuclease 1. Manvilla BA, Wauchope O, Seley-Radtke KL, et al. Biochemistry 50(48), 10540-9, (2011)

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Inhibition of the redox function of APE1/Ref-1 in myeloid leukemia cell lines results in a hypersensitive response to retinoic acid-induced differentiation and apoptosis. Fishel ML, Colvin ES, Luo M, et al. Exp. Hematol. 38(12), 1178-88, (2010)

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Splenectomy enhances liver regeneration through tumor necrosis factor (TNF)-alpha following dimethylnitrosamine-induced cirrhotic rat model. Murata K, Shiraki K, Sugimoto K, et al. Hepatogastroenterology. 48(40), 1022-7, (2001)

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Mad2 haploinsufficiency protects hematopoietic progenitor cells subjected to cell-cycle stress in vivo and to inhibition of redox function of Ape1/Ref-1 in vitro. Rohrabaugh SL, Hangoc G, Kelley MR, et al. Exp. Hematol. 39(4), 415-23, (2011)

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Augmentation of tumor necrosis factor family-induced apoptosis by E3330 in human hepatocellular carcinoma cell lines via inhibition of NF kappa B. Saitou Y, Shiraki K, Yamanaka T, et al. World J. Gastroenterol. 11(40), 6258-61, (2005)

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Apurinic/Apyrimidinic endonuclease 1 regulates inflammatory response in macrophages. Jedinak A, Dudhgaonkar S, Kelley MR, et al. Anticancer Res. 31(2), 379-85, (2011)

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