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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 Spec Table

CAS #Empirical Formula
412960-54-4C₂₇H₂₅Cl₂N₇O₇

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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®
      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
      Catalogue Number GTIN
      324521-25MGCN 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.