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

474790
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      Overview

      Replacement Information

      Key Spec Table

      Empirical FormulaCAS #
      C₂₆H₄₁N₃O₅133407-82-6

      Pricing & Availability

      Catalogue NumberAvailability Packaging Qty/Pack Price Quantity
      474790-10MG
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          Plastic ampoule 10 mg
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          474790-1MG
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              Plastic ampoule 1 mg
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              474790-20MG
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                  20 mg
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                  474790-5MG
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                      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

                      SDS

                      Title

                      Safety Data Sheet (SDS) 

                      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
                      Caspases and other Apoptosis Related Tools Brochure
                      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.