419820 ITK Inhibitor, BMS-509744 - CAS 439575-02-7 - Calbiochem

419820
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Empirical FormulaCAS #
C₃₂H₄₁N₅O₄S₂ 439575-02-7

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419820-5MG
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      Glass bottle 5 mg
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      Description
      OverviewA cell-permeable aminothioaryl-thiazolo compound that potently inhibits ITK kinase activity (IC50 = 19 nM; [ATP] = 1 µM) in an ATP-competitive manner by stabilizing ITK activation loop in a substrate-blocking, inactive conformation, inhibiting Fyn, IR, Lck, Btk only at much higher concentrations (IC50 ≥1.1 µM) and exhibiting little or no activity against 14 other kinases (IC50 ≥11 µM). Inhibits ITK-dependent cellular signaling (IC50 <300 nM against αCD3-stimulated PLCγ1 Tyr phosphorylation and Ca2+ mobilization in Jurkat cells) in vitro and alleviate OVA (Cat. No. 32467) challenge-induced airway leukocytes infiltration (ED50 = 25 mg/kg s.c.) in OVA-sensitized mice in vivo.
      Catalogue Number419820
      Brand Family Calbiochem®
      SynonymsBMS509744; EMT Inhibitor, IL-2-Inducible T Cell Kinase Inhibitor, N-(5-(5-(4-Acetylpiperazine-1-carbonyl)-4-methoxy-2-methylphenylthio)thiazol-2-yl)-4-((3,3-dimethylbutan-2-ylamino)methyl)benzamide, N-(5-((3-((4-Acetylpiperazin-1-yl)carbonyl)-4-methyl-6-methoxyphenyl)thio)thiazol-2-yl)-4-(N-1,2-dimethylpropylaminomethyl)benzamide
      References
      ReferencesKutach, A.K., et al. 2010. Chem. Biol. Drug Des. 76, 154.
      Das, J., et al. 2006. Bioorg. Med. Chem. Lett. 16, 3706.
      Lin, T.A., et al. 2004. Biochemistry 43, 11056.
      Product Information
      CAS number439575-02-7
      FormPale yellow powder
      Hill FormulaC₃₂H₄₁N₅O₄S₂
      Chemical formulaC₃₂H₄₁N₅O₄S₂
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetITK
      Primary Target IC<sub>50</sub>19 nM for ITK
      Purity≥97% 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 -20°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

      ITK Inhibitor, BMS-509744 - CAS 439575-02-7 - Calbiochem Certificates of Analysis

      TitleLot Number
      419820

      References

      Reference overview
      Kutach, A.K., et al. 2010. Chem. Biol. Drug Des. 76, 154.
      Das, J., et al. 2006. Bioorg. Med. Chem. Lett. 16, 3706.
      Lin, T.A., et al. 2004. Biochemistry 43, 11056.
      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.

      Revision22-February-2013 JSW
      SynonymsBMS509744; EMT Inhibitor, IL-2-Inducible T Cell Kinase Inhibitor, N-(5-(5-(4-Acetylpiperazine-1-carbonyl)-4-methoxy-2-methylphenylthio)thiazol-2-yl)-4-((3,3-dimethylbutan-2-ylamino)methyl)benzamide, N-(5-((3-((4-Acetylpiperazin-1-yl)carbonyl)-4-methyl-6-methoxyphenyl)thio)thiazol-2-yl)-4-(N-1,2-dimethylpropylaminomethyl)benzamide
      DescriptionA cell-permeable aminothioaryl-thiazolo compound that potently inhibits ITK kinase activity (IC50 = 19 nM; [ATP] = 1 µM) in an ATP-competitive manner by stabilizing ITK activation loop in a substrate-blocking, inactive conformation, inhibiting Fyn, IR, Lck, Btk only at much higher concentrations (IC50 = 1.1, 1.1, 2.4, and 4.1 µM, respectively) and exhibiting little or no activity against 14 other kinases (IC50 ≥11 µM). Inhibits ITK-dependent, but not ITK-independent, PLCγ1 tyrosine phosphorylation (IC50 <300 nM in αCD3-stimulated Jurkat T-cells) as well as downstream signaling events, including Ca2+ mobilization (IC50 = 52 nM in αCD3-stimulated Jurkat T-cells), IL-2 secretion (IC50 = 72, 250, 380, and 390 nM, respectively, in αCD3-stimulated EL4, Jurkat, murine splenocytes, and human PBMCs), and proliferation (IC50 = 430 nM against APC-induced primary human T-cell expansion). BMS-509744 is also efficacious in alleviating OVA (Cat. No. 32467) challenge-induced airway leukocytes infiltration (50% and 75% reduction, respectively, of total and eosinophil cell count; 25 mg/kg s.c.) in OVA- sensitized mice in vivo.
      FormPale yellow powder
      Intert gas (Yes/No) Packaged under inert gas
      CAS number439575-02-7
      Chemical formulaC₃₂H₄₁N₅O₄S₂
      Structure formulaStructure formula
      Purity≥97% by HPLC
      SolubilityDMSO (100 mg/ml)
      Storage -20°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
      ReferencesKutach, A.K., et al. 2010. Chem. Biol. Drug Des. 76, 154.
      Das, J., et al. 2006. Bioorg. Med. Chem. Lett. 16, 3706.
      Lin, T.A., et al. 2004. Biochemistry 43, 11056.