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

324521
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₂₇H₂₅Cl₂N₇O₇ 412960-54-4

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      324521-25MG
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          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®
          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
          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

          Documentation

          SDS

          Title

          Safety Data Sheet (SDS) 

          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 +2°C to +8°C
          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.
          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.