| Identification | Back Directory | [Name]
E 3330 | [CAS]
136164-66-4 | [Synonyms]
E 3330
CS-1756
APX3330
APX 3330
E 3330;E-3330
(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 | [EINECS(EC#)]
604-604-1 | [Molecular Formula]
C21H30O6 | [MDL Number]
MFCD00901331 | [MOL File]
136164-66-4.mol | [Molecular Weight]
378.46 |
| Chemical Properties | Back Directory | [Melting point ]
56-57 °C | [Boiling point ]
542.2±50.0 °C(Predicted) | [density ]
1.13±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [pka]
4.29±0.19(Predicted) | [color ]
red to orange | [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+ | [InChIKey]
AALSSIXXBDPENJ-FYWRMAATSA-N | [SMILES]
CCCCCCCCC\C(=C/C1=C(C)C(=O)C(OC)=C(OC)C1=O)C(O)=O |
| Hazard Information | Back Directory | [Uses]
E 3330 is a potent and selective APE1 inhibitor used in the treatment for age related macular degeneration. | [Uses]
E3330 has been used in the inhibition of endothelial cancer cells and apurinic/apyrimidinic endodeoxyribonuclease 1 (APEX1). | [Biological Activity]
ap endonuclease 1 (ape1) is a dual-function protein, which contains a redox domain and a dna repair domain. ape1 is overexpressed in numerous solid cancers, including prostate and bladder cancers, non-small cell lung cancers, gliomas, medulloblastomas and primitive neurectodermal tumors, osteosarcomas, and germ cell tumors. e3330 is a small molecule inhibitor of redox activity of ape1 protein. | [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. | [in vitro]
e3330 significantly reduces the growth of human pancreatic cancer cells in vitro. this phenomenon was further confirmed by a small interfering rna experiment to knockdown ape1 expression in pancreatic cancer cells. furthermore, the growth-inhibitory effects of e3330 are accentuated by hypoxia, and this is accompanied by striking inhibition in the dna binding ability of hypoxia-inducible factor-1α [1]. | [in vivo]
oral pretreatment with e3330 attenuated the elevation of plasma tumor necrosis factor activity and protected micefrom liver injury. furthermore, e3330 inhibited the production of tumor necrosis factor from cultured propionibacterium acnes-elicited murine peritoneal macrophages on stimulation with lipopolysaccharide in vitro [2]. | [References]
[1] gang-ming zou and anirban maitra. 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): 2012–2021.
[2] nagakawa j, hishinuma i, miyamoto k, hirota k, abe s, yamanaka t, katayama k, yamatsu i. protective effects of (2e)-3-[5-(2,3-dimethoxy-6-methyl-1,4- benzoquinoyl)]-2-nonyl-2-propenoic acid on endotoxin-mediated hepatitis in mice. j pharmacol exp ther. 1992 jul;262(1):145-50. |
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Sigma-Aldrich
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cjbscvictory
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