412512 IRE1 Inhibitor III, 4μ8C - CAS 14003-96-4 - Calbiochem

412512
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Key Specifications Table

Empirical FormulaCAS #
C₁₁H₈O₄ 14003-96-4

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412512-25MG
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      Glass bottle 25 mg
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      Description
      OverviewA cell-permeable coumarin o-hydroxyaldehyde that inhibits IRE1 RNase activity in a time- and dose-dependent manner (IC50 = 550 and 45 nM, respectively, with 0 and 16 min drug preincubation in RNA cleavage assays) by covalently targeting IRE1 Lys907 via Schiff base formation, effectively preventing ER stress-induced site-specific mRNA splicing as well as RIDD (Regulated IRE1-Dependent Degradation) mRNA degradation (IC50 = 6.9 and 4.1 µM, respectively, against Xbp1 splicing and Scara3 degradation) in MEF cultures following Tunicamycin (Cat. No. 654380) treatment. Comparing to STF083010 (Cat. No. 412510), 4μ8C is also shown to inhibit IRE1 autophosphorylation in cell-free assays via Schiff base formation with IRE1 Lys599 in the absence of ADP, however cellular nucleotide prevents 4μ8C from targeting IRE1 Lys599 intracellularly.
      Catalogue Number412512
      Brand Family Calbiochem®
      Synonyms8-Formyl-7-hydroxy-4-methylcoumarin, 7-Hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde, ER-to-Nucleus Signaling 1 Inhibitor III, Inositol-Reguiring Protein 1 Inhibitor III
      References
      ReferencesCross, B.C.S., et al. 2012. Proc. Natl. acad. Sci. USA 109, E869.
      Product Information
      CAS number14003-96-4
      FormYellow powder
      Hill FormulaC₁₁H₈O₄
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetIRE1
      Purity≥95% 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.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      IRE1 Inhibitor III, 4μ8C - CAS 14003-96-4 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      IRE1 Inhibitor III, 4μ8C - CAS 14003-96-4 - Calbiochem Certificates of Analysis

      TitleLot Number
      412512

      References

      Reference overview
      Cross, B.C.S., et al. 2012. Proc. Natl. acad. Sci. USA 109, E869.
      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.

      Revision11-October-2012 JSW
      Synonyms8-Formyl-7-hydroxy-4-methylcoumarin, 7-Hydroxy-4-methyl-2-oxo-2H-chromene-8-carbaldehyde, ER-to-Nucleus Signaling 1 Inhibitor III, Inositol-Reguiring Protein 1 Inhibitor III
      DescriptionA cell-permeable coumarin o-hydroxyaldehyde compound that inhibits IRE1 RNase activity in a time- and dose-dependent manner (IC50 = 550, 230, 180, 100, and 45 nM, respectively, with 0, 2, 4, 8, 16, min drug preincubation in FRET-based RNA cleavage assays) by covalently targeting IRE1 Lys907 via Schiff base formation, effectively preventing ER stress-induced site-specific mRNA splicing as well as RIDD (Regulated IRE1-Dependent Degradation) mRNA degradation (IC50 = 6.9 and 4.1 µM, respectively, against Xbp1 splicing and Scara3 degradation) in MEF cultures following Tunicamycin (Cat. No. 654380) treatment. Also demonstrated to inhibit ER capacity expansion (Effective conc. 32 µM) and amylase secretion (IC50 <2 µM) upon stress induction by Dexamethasone (Cat. No. 265005) treatment in rat AR42J tumoral acinar pancreatic cells. Structural analysis reveals that the reduced water accessibility to Lys907 in IRE1 native conformation accounts for the unusual stability of Lys907 Schiff base formation and forms the basis of selective IRE1 RNase inhibition by 4μ8C and STF083010 (Cat. No. 412510). Although 4μ8C, but not STF083010, is also shown to inhibit IRE1 autophosphorylation by Schiff base formation with IRE1 Lys599 in the absence of ADP, cellular nucleotide prevents 4μ8C from targeting IRE1 Lys599 and inhibiting IRE1 kinase activity intracellularly.
      FormYellow powder
      Intert gas (Yes/No) Packaged under inert gas
      CAS number14003-96-4
      Structure formulaStructure formula
      Purity≥95% by HPLC
      SolubilityDMSO (25 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.
      Toxicity Standard Handling
      ReferencesCross, B.C.S., et al. 2012. Proc. Natl. acad. Sci. USA 109, E869.