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E1286

Eeyarestatin I

Name: Eeyarestatin I
Brand: SIGMA

synthetic (organic), ≥98% (HPLC), ERAD inhibitor, powder

Synonym(s):

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

Empirical Formula (Hill Notation):

C₂₇H₂₅Cl₂N₇O₇

CAS Number:

412960-54-4

Molecular Weight:

630.44

MDL number:

MFCD00319108

UNSPSC Code:

12352204

NACRES:

NA.77

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Product Name

Eeyarestatin I, ≥98% (HPLC)

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

solubility

DMSO: 5 mg/mL

storage temp.

2-8°C

SMILES string

Clc1ccc(cc1)N2C(C(N(C2=O)CC(=O)NN=CC=Cc4[o]c(cc4)[N+](=O)[O-])(C)C)N(O)C(=O)Nc3ccc(cc3)Cl

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

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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ERAD inhibitors integrate ER stress with an epigenetic mechanism to activate BH3-only protein NOXA in cancer cells.

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

Targeted truncation of the ADAM17 cytoplasmic domain in mice results in protein destabilization and a hypomorphic phenotype.

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.

FoxO suppresses endoplasmic reticulum stress to inhibit growth of Tsc1-deficient tissues under nutrient restriction.

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

ADAM17 stabilizes its interacting partner inactive Rhomboid 2 (iRhom2) but not inactive Rhomboid 1 (iRhom1).

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

PrP-containing aggresomes are cytosolic components of an ER quality control mechanism.

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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Global Trade Item Number

SKU	GTIN
E1286-10MG	04061833234358

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