530587 Proteasome Inhibitor XXIII, PI-1840 - Calbiochem

530587
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical Formula
      C₂₂H₂₆N₄O₃

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      5.30587.0001
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          Glass bottle 10 mg
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          Description
          OverviewA cell-permeable, bioavailable, non-toxic pyridinyl-oxadiazoloisopropylamide compound that acts as a highly potent, selective, and non-covalent inhibitor of chymotrypsin-like (CT-L) activity of 20S proteasome (IC50 = 27 nM). Does not affect tyrpsin-like and postglutamyl-peptide-hydrolysis-like activities of proteasome even at higher concentrations (IC50 >> 100 µM). Its action appears to be readily reversible. Displays over 120-fold greater selectivity for the constitutive proteasome over the immunoproteasome (IC50 = 18 nM vs. 2.17 µM). Induces the accumulation of p27, IκBα and Bax in MDA-MB-468 cells and reduces the viability of a broad spectrum of cancer cells and triggers apoptosis. Shown to increase sensitivity of HCT-116 cells to Nutlin (Cat. No. 444143) by about four- fold, but does not affect p53 -/- HCT-116 cells. Also shown to enhance sensitivity of LNCaP cells to BCl-2 antagonist, BH3-M6 by four-fold, but does not affect DU-145 cells that lack Bax. Suppresses the growth of MDA-MB-231 xenografts in nude mice (150 mg/kg, i.p., q.d.).

          Please note that the molecular weight for this compound is batch-specific due to variable water content.
          Catalogue Number530587
          Brand Family Calbiochem®
          SynonymsN-Isopropyl-2-(4-propylphenoxy)-N-((3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide, PI1840
          References
          ReferencesKazi, A., et al. 2014. J. Biol. Chem. 289, 11906.
          Ozcan, S., et al. 2013. J. Med. Chem. 56, 3783.
          Product Information
          FormWhite solid
          Hill FormulaC₂₂H₂₆N₄O₃
          Chemical formulaC₂₂H₂₆N₄O₃
          ReversibleY
          Structure formula ImageStructure formula Image
          Applications
          Biological Information
          Primary Targetchymotrypsin-like activity of 20S proteasome
          Primary Target IC<sub>50</sub>27 nM for chymotrypsin-like (CT-L) activity of 20S proteasome
          Purity≥98% by HPLC
          Physicochemical Information
          Cell permeableY
          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 +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 6 months at -20°C.
          Packaging Information
          Packaged under inert gas Packaged under inert gas
          Transport Information
          Supplemental Information
          Specifications

          Documentation

          Proteasome Inhibitor XXIII, PI-1840 - Calbiochem SDS

          Title

          Safety Data Sheet (SDS) 

          References

          Reference overview
          Kazi, A., et al. 2014. J. Biol. Chem. 289, 11906.
          Ozcan, S., et al. 2013. J. Med. Chem. 56, 3783.
          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.

          Revision15-August-2014 JSW
          SynonymsN-Isopropyl-2-(4-propylphenoxy)-N-((3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide, PI1840
          DescriptionA cell-permeable pyridinyl-oxadiazoloisopropylamide compound that selectively inhibits 20S proteasome β5 CT-L/chymotrypsin-like over β1 C-L/caspase-like (PGPH-L/postglutamyl-peptide hydrolase-like) activity and β2 T-L/trypsin-like activity (IC50 = 18 nM against CT-L and <100 µM against C-L & T-L activity of rabbit 20S proteasome using 20 µM Suc-LLVY-AMC/Cat. No. 539142, Z-LLE-AMC/Cat. No. 539141, and Bz-VGR-AMC as substrate, respectively; 1 h at 37°C) in a noncovalent and reversible manner, being superior to Bortezomib (Cat. No. 504314) in proteasome selectivity over hematopoietic immunoproteasome (120-fold vs. 2-fold selectivity, respectively, in CT-L assays using rabbit proteasome & immunoproteasome). Culture treatment is shown to result in fast cellular CT-L inhibition (>90% of max inhibition within 10 min in MDA-MB-468; 5 µM), resulting in upregulation of proapoptic p27, IκB-α, Bax, as well as Capase-3 & PARP cleavage with concomitant downregulation of Akt & Survivin and phosphorylation of Akt and S6 (20 µM for 48 h in MDA-MB-468 cultures). Shown to exhibits antiproliferation activity in 12 human cancer cultures (IC50 in 5 d from 2.2 µM/MDA-MB-468 to 45.2 µM/RXF 397 by MTT assay), while being less potent against non-cancer HCA2 fibroblast and MCF-10A mammary epithelial cells ((IC50 in 5 d = 86 & 314 µM, respectively), and selectively enhances Nutlin (Cat. No. 444152) sensitivity in p53+/+, but not p53-/-, HCT-116 cultures. Daily intraperitoneal injection (150 mg/kg/d) is reported to result in 76% retardation of MDA-MB-468-derived tumor growth at the end of a 14 d treatment period among mice in vivo with no apparent weight loss, Bortezomib treatment (1 mg/kg, twice weekly i.p.), in comparison, is reported to result in a loss of 6.21% body weight with no significant tumor growth inhibiton.
          FormWhite solid
          Intert gas (Yes/No) Packaged under inert gas
          Chemical formulaC₂₂H₂₆N₄O₃
          Structure formulaStructure formula
          Purity≥98% by HPLC
          SolubilityDMSO (50 mg/ml)
          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 6 months at -20°C.
          Toxicity Standard Handling
          ReferencesKazi, A., et al. 2014. J. Biol. Chem. 289, 11906.
          Ozcan, S., et al. 2013. J. Med. Chem. 56, 3783.