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504712 β-Catenin/Tcf Inhibitor VI, ICG-001 - CAS 847591-62-2 - Calbiochem

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Synonymes: ICG001, Wnt Pathway Inhibitor XX, (6S,9aS)-Hexahydro-6-((4-hydroxyphenyl)methyl)-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide, (6S)-N-Benzyl-6-(p-hydroxyphenylmethyl)-8-(1-naphthylmethyl)-4,7-dioxohexahydro-2H-pyrazino[1,2-a]pyrimidine-1-carboxamide

Primary Target: CREB-binding protein
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504712
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Replacement Information

Tableau de caractéristiques principal

CAS #Empirical Formula
847591-62-2C₃₃H₃₂N₄O₄

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      Description
      OverviewA cell-permeable pyrazinopyrimidinecarboxamide that competes against β-catenin for CBP (CREB-binding protein) binding and selectively prevents CBP- but not p300-, dependent TCF/β-catenin transcriptional regulations both in cultures in vitro (5 to 25 µM) and in mice in vivo (5 mg/kg/day via osmotic pump infusion), while not affecting CBP-dependent transcriptional activities mediated by the AP-1 or CRE complex. Shown to reactivate p300//TCF/β-catenin-mediated neuronal differentiation upon NGF stimulation in PS-1 L286V mutant-expressing PC-12 cultures and be efficacious in alleviating bleomycin- (0,08 units/50 µL/mouse; administered intranasally; Cat. No. 203401) induced pulmonary fibrosis in mice.
      Catalogue Number504712
      Brand Family Calbiochem®
      SynonymsICG001, Wnt Pathway Inhibitor XX, (6S,9aS)-Hexahydro-6-((4-hydroxyphenyl)methyl)-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide, (6S)-N-Benzyl-6-(p-hydroxyphenylmethyl)-8-(1-naphthylmethyl)-4,7-dioxohexahydro-2H-pyrazino[1,2-a]pyrimidine-1-carboxamide
      References
      ReferencesYan, D., et al. 2012. J. Biol. Chem. 287, 8598.
      Henderson, W.R. Jr, et al. 2010. Proc. Natl. Acad. Sci. USA. 107, 14309.
      Eguchi, M., et al. 2005. Med Chem. 1, 467.
      Ma, H., et al. 2005. Oncogene. 24, 3619.
      Teo, J.L., et al. 2005. Proc. Natl. Acad. Sci. USA. 102, 12171.
      Emami, K.H., et al. 2004. Proc. Natl. Acad. Sci. USA. 101, 12682.
      Product Information
      CAS number847591-62-2
      FormOff-white powder
      Hill FormulaC₃₃H₃₂N₄O₄
      Chemical formulaC₃₃H₃₂N₄O₄
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetCREB-binding protein
      Purity≥99% 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 3 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Référence GTIN
      5.04712.0001 04055977244052

      Documentation

      β-Catenin/Tcf Inhibitor VI, ICG-001 - CAS 847591-62-2 - Calbiochem FDS

      Titre

      Fiche de données de sécurité des matériaux (FDS) 

      Références bibliographiques

      Aperçu de la référence bibliographique
      Yan, D., et al. 2012. J. Biol. Chem. 287, 8598.
      Henderson, W.R. Jr, et al. 2010. Proc. Natl. Acad. Sci. USA. 107, 14309.
      Eguchi, M., et al. 2005. Med Chem. 1, 467.
      Ma, H., et al. 2005. Oncogene. 24, 3619.
      Teo, J.L., et al. 2005. Proc. Natl. Acad. Sci. USA. 102, 12171.
      Emami, K.H., et al. 2004. Proc. Natl. Acad. Sci. USA. 101, 12682.
      Fiche technique

      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.

      Revision26-July-2013 JSW
      SynonymsICG001, Wnt Pathway Inhibitor XX, (6S,9aS)-Hexahydro-6-((4-hydroxyphenyl)methyl)-8-(1-naphthalenylmethyl)-4,7-dioxo-N-(phenylmethyl)-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide, (6S)-N-Benzyl-6-(p-hydroxyphenylmethyl)-8-(1-naphthylmethyl)-4,7-dioxohexahydro-2H-pyrazino[1,2-a]pyrimidine-1-carboxamide
      DescriptionA cell-permeable pyrazinopyrimidinecarboxamide that competes against β-catenin for CBP (CREB-binding protein) binding (5 to 10 µM for 24 h in SW480 and C2C12 cultures) and selectively prevents CBP- but not p300-, dependent TCF/β-catenin transcriptional regulations both in cultures in vitro (5 to 25 µM in SW480, HCT116, rat RLT-6TN, and primary human IPF lung fibroblasts; 4 to 24 h) and in mice in vivo (5 mg/kg/day via osmotic pump infusion), while not affecting CBP-dependent transcriptional activities mediated by the AP-1 or CRE complex. Selective blockage of CBP/TCF/β-catenin complex formation by ICG-001 is shown to reactivate p300//TCF/β-catenin-mediated neuronal differentiation upon NGF stimulation in PS-1 L286V mutant-expressing PC-12 cultures (cell population with neurite outgrowth = 90% and 17% of wt PS-1 control level, respectively, with or without 10 µM ICG-001) and be efficacious in alleviating bleomycin- (0,08 units/50 µL/mouse; administered intranasally; Cat. No. 203401) induced pulmonary fibrosis in mice (5 mg/kg/day via osmotic pump infusion; 10 d treatment starting 1 d before bleomycin induction or 21 d treatment starting d 21 post bleomycin induction).
      FormOff-white powder
      Intert gas (Yes/No) Packaged under inert gas
      CAS number847591-62-2
      Chemical formulaC₃₃H₃₂N₄O₄
      Structure formulaStructure formula
      Purity≥99% by HPLC
      SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
      Storage Protect from light
      +2°C to +8°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
      Toxicity Standard Handling
      ReferencesYan, D., et al. 2012. J. Biol. Chem. 287, 8598.
      Henderson, W.R. Jr, et al. 2010. Proc. Natl. Acad. Sci. USA. 107, 14309.
      Eguchi, M., et al. 2005. Med Chem. 1, 467.
      Ma, H., et al. 2005. Oncogene. 24, 3619.
      Teo, J.L., et al. 2005. Proc. Natl. Acad. Sci. USA. 102, 12171.
      Emami, K.H., et al. 2004. Proc. Natl. Acad. Sci. USA. 101, 12682.