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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: 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, EerI, ES1, Valosin-containing Protein Inhibitor II, VCP Inhibitor II, ERAD Inhibitor II, p97 Inhibitor II

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324521
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Overview

Replacement Information

Key Specifications Table

CAS #Empirical Formula
412960-54-4C₂₇H₂₅Cl₂N₇O₇

Products

Catalog NumberPackaging Qty/Pack
324521-25MG Glass bottle 25 mg
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®
Synonyms1-(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, EerI, ES1, Valosin-containing Protein Inhibitor II, VCP Inhibitor II, ERAD Inhibitor II, p97 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
Applications
Biological Information
Purity≥90% by HPLC
Physicochemical Information
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
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
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalog Number GTIN
324521-25MG 04055977197358

Documentation

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

Title

Safety Data Sheet (SDS) 

Eeyarestatin I - CAS 412960-54-4 - Calbiochem Certificates of Analysis

TitleLot Number
324521

References

Reference overview
Chou, 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.
Data Sheet

Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

Revision21-October-2011 RFH
Synonyms1-(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, EerI, ES1, Valosin-containing Protein Inhibitor II, VCP Inhibitor II, ERAD Inhibitor II, p97 Inhibitor II
DescriptionA cell-permeable oxo-imidazolidinyl-hydroxyurea whose cellular metabolite is shown to effectively inhibit the 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) ATPase complex and a blockage of the p97 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.
FormLight yellow-orange solid
Intert gas (Yes/No) Packaged under inert gas
CAS number412960-54-4
Chemical formulaC₂₇H₂₅Cl₂N₇O₇
Structure formulaStructure formula
Purity≥90% by HPLC
SolubilityDMSO (100 mg/ml). It is recommended to prepare a stock solution for 3 month use each time and store the unreconstituted material in solid form, protected from moisture and preferably under inert gas, for best long-term stability during storage.
Storage Protect from light
+2°C to +8°C
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.
Toxicity Standard Handling
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.