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Merck
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Key Documents

E1286

Sigma-Aldrich

Eeyarestatin I

≥98% (HPLC)

Sinónimos:

3-(4-Chlorophenyl)-4-[[[(4-chlorophenyl)amino]carbonyl]hydroxyamino]-5,5-dimethyl-2-oxo-1-imidazolidineacetic acid 2-[3-(5-nitro-2-furanyl)-2-propen-1-ylidene]hydrazide

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About This Item

Fórmula empírica (notación de Hill):
C27H25Cl2N7O7
Número de CAS:
412960-54-4
Peso molecular:
630.44
UNSPSC Code:
12352204
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

solubility

DMSO: 5 mg/mL

storage temp.

2-8°C

InChI

1S/C27H25Cl2N7O7/c1-27(2)24(35(40)25(38)31-19-9-5-17(28)6-10-19)34(20-11-7-18(29)8-12-20)26(39)33(27)16-22(37)32-30-15-3-4-21-13-14-23(43-21)36(41)42/h3-15,24,40H,16H2,1-2H3,(H,31,38)(H,32,37)

InChI key

JTUXTPWYZXWOIB-UHFFFAOYSA-N

Biochem/physiol Actions

Eeyarestatin I is a potent inhibitor of endoplasmic reticulum associated protein degradation (ERAD). Specifically targets the p97-associated deubiquinating process (PAD) and inhibits ataxin-3 (atx3)-dependent deubiquitination. Also inhibits Sec61-mediated protein translocation at the ER. Displays cytotoxic activity preferentially against cancer cells; induces cell death via the proapoptotic protein NOXA.
Eeyarestatin I or Eer1 promotes transcriptional activation of the pro-apoptotic protein NOXA by inducing activation of the NOXA transcription factors ATF3 and ATF4 and by inhibiting the degradation of histone H2A by blocking its ubiquitination.

Other Notes

This product is a mixture of E/Z imine isomers

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Qiuyan Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(7), 2200-2205 (2009-01-24)
The ubiquitin-proteasome system has recently emerged as a major target for drug development in cancer therapy. The proteasome inhibitor bortezomib has clinical activity in multiple myeloma and mantle cell lymphoma. Here we report that Eeyarestatin I (EerI), a chemical inhibitor
Jose Lora et al.
The Journal of biological chemistry, 296, 100733-100733 (2021-05-07)
A disintegrin and metalloprotease 17 (ADAM17) is a cell-surface metalloprotease that serves as the principle sheddase for tumor necrosis factor α (TNFα), interleukin-6 receptor (IL-6R), and several ligands of the epidermal growth factor receptor (EGFR), regulating these crucial signaling pathways.
Gisela Weskamp et al.
The Journal of biological chemistry, 295(13), 4350-4358 (2020-02-16)
The metalloprotease ADAM17 (a disintegrin and metalloprotease 17) is a key regulator of tumor necrosis factor α (TNFα), interleukin 6 receptor (IL-6R), and epidermal growth factor receptor (EGFR) signaling. ADAM17 maturation and function depend on the seven-membrane-spanning inactive rhomboid-like proteins
Avantika Gupta et al.
eLife, 9 (2020-06-12)
The transcription factor FoxO has been shown to block proliferation and progression in mTORC1-driven tumorigenesis but the picture of the relevant FoxO target genes remains incomplete. Here, we employed RNA-seq profiling on single clones isolated using laser capture microdissection from
Tatyana Dubnikov et al.
Journal of cell science, 129(19), 3635-3647 (2016-08-24)
Limited detoxification capacity often directs aggregation-prone, potentially hazardous, misfolded proteins to be deposited in designated cytosolic compartments known as 'aggresomes'. The roles of aggresomes as cellular quality control centers, and the cellular origin of the deposits contained within these structures
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