Eeyarestatin I

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Cat.No. 3922 - Eeyarestatin I | C27H25Cl2N7O7 | CAS No. 412960-54-4
Description: Potent inhibitor of ER-associated protein degradation and translocation
Chemical Name: 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
Purity: ≥98% (HPLC)
Datasheet
Citations (4)
Reviews
Literature (1)

Biological Activity

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. Also enhances adeno-acssociated viral transduction in multiple cells types.

Technical Data

M. Wt 630.44
Formula C27H25Cl2N7O7
Storage Desiccate at +4°C
Purity ≥98% (HPLC)
CAS Number 412960-54-4
PubChem ID 23947580
InChI Key JTUXTPWYZXWOIB-LWWHHIEBSA-N
Smiles O=C1N(C2=CC=C(Cl)C=C2)C(N(O)C(NC4=CC=C(Cl)C=C4)=O)C(C)(C)N1CC(N/N=C/C=C/C3=CC=C([N+]([O-])=O)O3)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 63.04 100

Preparing Stock Solutions

The following data is based on the product molecular weight 630.44. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.59 mL 7.93 mL 15.86 mL
5 mM 0.32 mL 1.59 mL 3.17 mL
10 mM 0.16 mL 0.79 mL 1.59 mL
50 mM 0.03 mL 0.16 mL 0.32 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Wang et al (2008) Inhibition of p97-dependent protein degradation by eeyarestatin I. J.Biol.Chem. 283 7445 PMID: 18199748

Aletrari et al (2011) Eeyarestatin 1 interferes with both retrograde and anterograde intracellular trafficking pathways. PLoS One 6 e22713 PMID: 21799938

Wang et al (2008) ERAD inhibitors integrate ER stress with an epigenetic mechanism to activate BH3-only protein NOXA in cancer cells. Proc.Natl.Acad.Sci.USA 106 2200

Cross et al (2009) Eeyarestatin I inhibits Sec61-mediated protein translocation at the endoplasmic reticulum. J.Cell Science 122 4393

Berry and Asokan et al (2016) Chemical modulation of endocytic sorting augments adeno-associated viral transduction. J.Biol.Chem. 291 939 PMID: 26527686


If you know of a relevant reference for Eeyarestatin I, please let us know.

Keywords: Eeyarestatin I, Eeyarestatin I supplier, endoplasmic, reticulum, ER, associated, protein, degradation, ERAD, translocation, inhibitors, inhibits, ER-stress, viral, transduction, enhancers, enhances, Translocation,, Exocytosis, &, Endocytosis, Other, stress/UPR, Translocation, Viral, Transduction, Enhancers, 3922, Tocris Bioscience

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