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324521 Eeyarestatin I - CAS 412960-54-4 - Calbiochem

A cell-permeable oxo-imidazolidinyl-hydroxyurea that localizes to ER, where it interacts with AAA ATPase p97 via its nitrofuran-containing moiety, without exhibiting affinity toward Hsp70 / ATPase NSF

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: ES1, EerI, 1-(4-Chloro-phenyl)-3-(3-(4-chloro-phenyl)-5,5-dimethyl-1-(3-(5-nitro-furan-2-yl)-allyldiene-hydrazinocarbonylmethyl)-2-oxo-imidazolidin-4-yl)-1-hydroxyl-urea, ERAD Inhibitor II, p97 Inhibitor II, Valosin-containing Protein Inhibitor II, VCP Inhibitor II

324521
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Overview

Key Spec Table

CAS #Empirical Formula
412960-54-4C₂₇H₂₅Cl₂N₇O₇

Products

Catalogue NumberPackaging Qty/Pack
324521-25MG Glass bottle 25 mg
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Description
OverviewA cell-permeable oxo-imidazolidinyl-hydroxyurea that preferentially localizes to ER, where it interacts with AAA (ATPase associated with diverse cellular activities) ATPase p97 (Kd = 5 - 10 µM) via its nitrofuran-containing moiety, without exhibiting affinity toward Hsp70 or AAA ATPase NSF (N-methylmaleimide-sensitive factor). Evidence indicates that EerI cellular metabolite, but not EerI itself, is responsible for the inhibition of ER membrane translocon sec61 complex-mediated transfer of newly synthesized polypeptide, resulting in a blockage of ER-mediated posttranslational glycosylation and signal peptide removal (Effective conc. = 8 µM in HepG2 and HeLa cultures). Ether independent or as a consequence of the early effect on sec61 complex, EerI culture treatment also induces a selective dissociation of an 180 kDa protein from the atx3-containing p97/VCP (Valosin-containing protein) complex and a blockage of the complex-associated deubiquitination of ERAD (ER-associated protein degradation) substrates in a reversible manner, resulting in an accumulation of polyubiquitinated proteins (Effective conc. = 10 µM in A9 and 293T cultures). EerI culture treatment (10 µM) is also demonstrated to selectively induce cytotoxicity in lymphoid cell lines, BJAB, HBL-2, JEKO-1, Jurkat, KMS-12, MINO, as well as primary leukemia cells from CLL (chronic lymphocytic leukemia) patients, but not PBMC from healthy donors, by upregulating the BH3-only pro-apoptotic protein NOXA in cancer cells via ATF3/4 activation and a downregulation of H2A ubiquitination. Unlike DBeQ (Cat. No. 506190), EeRI does not inhibit p97 ATPase activity.
Catalogue Number324521
Brand Family Calbiochem®
SynonymsES1, EerI, 1-(4-Chloro-phenyl)-3-(3-(4-chloro-phenyl)-5,5-dimethyl-1-(3-(5-nitro-furan-2-yl)-allyldiene-hydrazinocarbonylmethyl)-2-oxo-imidazolidin-4-yl)-1-hydroxyl-urea, ERAD Inhibitor II, p97 Inhibitor II, Valosin-containing Protein Inhibitor II, VCP Inhibitor II
References
ReferencesChou, T.F., et al. 2011. Proc. Natl. Acad. Sci. USA 108, 4834.
Wang. Q, et al. 2010. PLoS ONE 5, e15479.
Cross, B.C.S., et al. 2009. J. Cell. Sci. 122, 4393.
Wang, Q., et al. 2009. Proc. Natl. Acad. Sci. USA 106, 2200.
Wang, Q., et al. 2008. J. Biol. Chem. 283, 7445.
Fiebiger, E., et al. 2004. Mol. Biol. Cell 15, 1635.
Product Information
CAS number412960-54-4
FormLight yellow-orange solid
Hill FormulaC₂₇H₂₅Cl₂N₇O₇
Chemical formulaC₂₇H₂₅Cl₂N₇O₇
Structure formula ImageStructure formula Image
Quality LevelMQ100
Biological Information
Purity≥90% by HPLC
Storage and Shipping Information
Ship Code Shipped at Ambient Temperature or with Blue Ice or with Dry Ice
Toxicity Standard Handling
Storage +2°C to +8°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Packaging Information
Packaged under inert gas Packaged under inert gas
Global Trade Item Number
Catalogue Number GTIN
324521-25MG 04055977197358