474790 MG-132 - CAS 133407-82-6 - Calbiochem

474790
  
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₂₆H₄₁N₃O₅ 133407-82-6
      Description
      OverviewA potent, reversible, and cell-permeable proteasome inhibitor (Ki = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable strains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. Activates c-Jun N-terminal kinase (JNK1), which initiates apoptosis. Inhibits NF-κB activation (IC50 = 3 µM). Also reported to increases the survival rate of mesenchymal stem cells following their transplantation. Prevents β-secretase cleavage. A 10 mM (1 mg/210 µl) solution of MG-132 (Cat. No. 474791) in DMSO is also available. This material is ≥98% pure by HPLC. A material with ≥95% purity by HPLC (Cat. No. 474787) is also available.
      Catalogue Number474790
      Brand Family Calbiochem®
      SynonymsCarbobenzoxy-L-leucyl-L-leucyl-L-leucinal, Z-LLL-CHO, Proteasome Inhibitor XI
      References
      ReferencesLi, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
      Steinhilb, M.L., et al. 2001. J. Biol. Chem. 276, 4476.
      Meriin, A.B., et al. 1998. J. Biol. Chem. 273, 6373.
      Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem. 31, 279.
      Klafki, H.W., et al. 1996. J. Biol. Chem. 271, 2865.
      Lee, D.H., and Goldberg, A.L., 1996. J. Biol. Chem. 271, 27280.
      Wiertz, E.J., et al. 1996. Cell 84, 769.
      Jensen, T.J., et al. 1995. Cell 83, 129.
      Read, M.A., et al. 1995. Immunity 2, 493.
      Rock, K.L., et al. 1994. Cell 78, 761.
      Product Information
      CAS number133407-82-6
      ATP CompetitiveN
      FormWhite solid
      Hill FormulaC₂₆H₄₁N₃O₅
      Chemical formulaC₂₆H₄₁N₃O₅
      ReversibleY
      Structure formula ImageStructure formula Image
      Applications
      Biological Information
      Primary Targetproteasome
      Primary Target IC<sub>50</sub>3 µM against NF-κB activation
      Primary Target K<sub>i</sub>4 nM against proteasome
      Purity≥98% by HPLC
      Physicochemical Information
      Cell permeableY
      Peptide SequenceZ-Leu-Leu-Leu-CHO
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      Safety Information
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Standard Handling
      Storage -20°C
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Packaging Information
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      MG-132 - CAS 133407-82-6 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      MG-132 - CAS 133407-82-6 - Calbiochem Certificates of Analysis

      TitleLot Number
      474790

      References

      Reference overview
      Li, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
      Steinhilb, M.L., et al. 2001. J. Biol. Chem. 276, 4476.
      Meriin, A.B., et al. 1998. J. Biol. Chem. 273, 6373.
      Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem. 31, 279.
      Klafki, H.W., et al. 1996. J. Biol. Chem. 271, 2865.
      Lee, D.H., and Goldberg, A.L., 1996. J. Biol. Chem. 271, 27280.
      Wiertz, E.J., et al. 1996. Cell 84, 769.
      Jensen, T.J., et al. 1995. Cell 83, 129.
      Read, M.A., et al. 1995. Immunity 2, 493.
      Rock, K.L., et al. 1994. Cell 78, 761.

      Brochure

      Title
      Proteasomes Technical Bulletin

      Citations

      Title
    • Li, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
    • Kamynina, E., et al. 2007. Molecular and Cellular Biology 27, 1809.
    • Yolanda Fernandez, et al. (2006) Chemical Blockage of the Proteasome Inhibitory Function of Bortezomib: Impact on Tumor Cell Death. Journal of Biological Chemistry 281, 1107-1118.
    • Markus D. Lacher, et al. (2006) Transforming Growth Factor-{beta} Receptor Inhibition Enhances Adenoviral Infectability of Carcinoma Cells via Up-Regulation of Coxsackie and Adenovirus Receptor in Conjunction with Reversal of Epithelial-Mesenchymal Transition. Cancer Research 66, 1648-1657.
    • Chen, L., et al. 2005. Molecular Cancer Therapeutics 4, 1311.
    • Emily I. Chen, et al. (2005) Maspin alters the carcinoma proteome. FASEB Journal in press,.
    • Siva Kumar Kolluri, et al. (2005) The R-enantiomer of the nonsteroidal antiinflammatory drug etodolac binds retinoid X receptor and induces tumor-selective apoptosis. Procedings of the National Academy of Science 102, 2525-2530.
    • Zaibo Li, et al. (2005) VHL protein-interacting deubiquitinating enzyme 2 deubiquitinates and stabilizes HIF-1α. European Molecular Biology Organization Reports 6, 373-378.
    • Yasuyuki Miyake, et al. (2005) Novel splicing variant of mouse orc1 is deficient in nuclear translocation and resistant for proteasome-mediated degradation. Journal of Biological Chemistry 280, 12643-12652.
    • Dana Ungermannova, Yuefeng Gao and Xuedong Liu. (2005) Ubiquitination of p27Kip1 requires physical interaction with cyclin E and probable phosphate recognition by SKP2. Journal of Biological Chemistry 280, 30301-30309.
    • Chuan-Jin Wu, et al. (2005) TNF-α induced c-IAP1/TRAF2 complex translocation to a Ubc6-containing compartment and TRAF2 ubiquitination. European Molecular Biology Organization Journal 24, 1886-1898.
    • Zhigang Zhang, Jin-Ying Wu, William Hait and Jin-Ming Yang. (2004) Regulation of the stability of P-glycoprotein by ubiquitination.. Molecular Pharmacology 66, 395-403.
    • Gloria Bonuccelli, et al. (2003) Proteasome inhibitor (MG-132) treatment of mdx mice rescues the expression and membrane localization of dystrophin and dystrophin-associated proteins. American Journal of Pathology 163, 1663-1675.
    • 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.

      Revision27-February-2012 RFH
      SynonymsCarbobenzoxy-L-leucyl-L-leucyl-L-leucinal, Z-LLL-CHO, Proteasome Inhibitor XI
      DescriptionPotent, reversible, and cell-permeable proteasome inhibitor (Ki = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable stains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. Activates c-Jun N-terminal kinase (JNK1) which initiates apoptosis. Inhibits NF-kB activation (IC50 = 3 µM). Also reported to increases the survival rate of mesenchymal stem cells following their transplantation.
      FormWhite solid
      CAS number133407-82-6
      Chemical formulaC₂₆H₄₁N₃O₅
      Peptide SequenceZ-Leu-Leu-Leu-CHO
      Structure formulaStructure formula
      Purity≥98% by HPLC
      SolubilityDMSO (20 mg/ml) or Ethanol (20 mg/ml)
      Storage -20°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Toxicity Standard Handling
      ReferencesLi, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
      Steinhilb, M.L., et al. 2001. J. Biol. Chem. 276, 4476.
      Meriin, A.B., et al. 1998. J. Biol. Chem. 273, 6373.
      Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem. 31, 279.
      Klafki, H.W., et al. 1996. J. Biol. Chem. 271, 2865.
      Lee, D.H., and Goldberg, A.L., 1996. J. Biol. Chem. 271, 27280.
      Wiertz, E.J., et al. 1996. Cell 84, 769.
      Jensen, T.J., et al. 1995. Cell 83, 129.
      Read, M.A., et al. 1995. Immunity 2, 493.
      Rock, K.L., et al. 1994. Cell 78, 761.
      Citation
    • Li, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
    • Kamynina, E., et al. 2007. Molecular and Cellular Biology 27, 1809.
    • Yolanda Fernandez, et al. (2006) Chemical Blockage of the Proteasome Inhibitory Function of Bortezomib: Impact on Tumor Cell Death. Journal of Biological Chemistry 281, 1107-1118.
    • Markus D. Lacher, et al. (2006) Transforming Growth Factor-{beta} Receptor Inhibition Enhances Adenoviral Infectability of Carcinoma Cells via Up-Regulation of Coxsackie and Adenovirus Receptor in Conjunction with Reversal of Epithelial-Mesenchymal Transition. Cancer Research 66, 1648-1657.
    • Chen, L., et al. 2005. Molecular Cancer Therapeutics 4, 1311.
    • Emily I. Chen, et al. (2005) Maspin alters the carcinoma proteome. FASEB Journal in press,.
    • Siva Kumar Kolluri, et al. (2005) The R-enantiomer of the nonsteroidal antiinflammatory drug etodolac binds retinoid X receptor and induces tumor-selective apoptosis. Procedings of the National Academy of Science 102, 2525-2530.
    • Zaibo Li, et al. (2005) VHL protein-interacting deubiquitinating enzyme 2 deubiquitinates and stabilizes HIF-1α. European Molecular Biology Organization Reports 6, 373-378.
    • Yasuyuki Miyake, et al. (2005) Novel splicing variant of mouse orc1 is deficient in nuclear translocation and resistant for proteasome-mediated degradation. Journal of Biological Chemistry 280, 12643-12652.
    • Dana Ungermannova, Yuefeng Gao and Xuedong Liu. (2005) Ubiquitination of p27Kip1 requires physical interaction with cyclin E and probable phosphate recognition by SKP2. Journal of Biological Chemistry 280, 30301-30309.
    • Chuan-Jin Wu, et al. (2005) TNF-α induced c-IAP1/TRAF2 complex translocation to a Ubc6-containing compartment and TRAF2 ubiquitination. European Molecular Biology Organization Journal 24, 1886-1898.
    • Zhigang Zhang, Jin-Ying Wu, William Hait and Jin-Ming Yang. (2004) Regulation of the stability of P-glycoprotein by ubiquitination.. Molecular Pharmacology 66, 395-403.
    • Gloria Bonuccelli, et al. (2003) Proteasome inhibitor (MG-132) treatment of mdx mice rescues the expression and membrane localization of dystrophin and dystrophin-associated proteins. American Journal of Pathology 163, 1663-1675.