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

474790
Purchase on Sigma-Aldrich

Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
133407-82-6C₂₆H₄₁N₃O₅

Products

Catalogue NumberPackaging Qty/Pack
474790-10MG Plastic ampoule 10 mg
474790-1MG Plastic ampoule 1 mg
474790-20MG 20 mg
474790-5MG Plastic ampoule 5 mg
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
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.