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

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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
                  Quality LevelMQ100
                  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.