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557360 Roscovitine - CAS 186692-46-6 - Calbiochem

Roscovitine, CAS 186692-46-6, is a potent, reversible, and selective inhibitor of CDKs. Displays 10 to 20 fold greater potency for p34cdk1, p33cdk2, and p33cdk5 relative to Olomoucine.

Roscovitine - CAS 186692-46-6 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: 2-(R)-(1-Ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine, Cdk7 Inhibitor I

Primary Target: p34cdk1/cyclin B
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557360
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Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
186692-46-6C₁₉H₂₆N₆O

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      Description
      OverviewA potent, reversible, and selective inhibitor of cyclin-dependent kinases (Cdks) that exhibits about ten-fold greater efficacy towards p34cdk1 and p33cdk2 and twenty-fold greater efficacy towards p33cdk5 relative to Olomoucine (Cat. No. 495620). Inhibits p34cdk1/cyclin B (IC50 = 650 nM), p33cdk2/cyclin A (IC50 = 700 nM), p33cdk2/cyclin E (IC50 = 700 nM), and p33cdk5/p35 (IC50 = 200 nM) by competing for the ATP binding domain of the kinases. Exhibits reduced sensitivity towards related kinases including ERK1 and ERK2 (IC50 = 34 µM and 14 µM, respectively). Roscovitine does not significantly affect the activity of other protein kinases even at 100 µM, including p34cdk4/cyclin D1 and p40cdk6/cyclin D2. Compared to olomoucine, roscovitine displays increased anti-mitotic activity at the G1/S and G2/M phases of the cell cycle. A 50 mM (5 mg/282 µl) solution of Roscovitine (Cat. No. 557364) in DMSO is also available.
      Catalogue Number557360
      Brand Family Calbiochem®
      Synonyms2-(R)-(1-Ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine, Cdk7 Inhibitor I
      References
      ReferencesDe Azevedo, W.F., et al. 1997. Eur. J. Biochem. 243, 518.
      Meijer, L., et al. 1997. Eur. J. Biochem. 243, 527.
      Meijer, L., et al. 1996. Trends Cell Biol. 6, 393.
      Rudolph, B., et al. 1996. EMBO J. 15, 3053.
      Product Information
      CAS number186692-46-6
      ATP CompetitiveN
      DeclarationSold under license of U.S. Patent 6,316,456
      FormWhite to off-white solid
      Hill FormulaC₁₉H₂₆N₆O
      Chemical formulaC₁₉H₂₆N₆O
      ReversibleY
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      ApplicationRoscovitine, CAS 186692-46-6, is a potent, reversible, and selective inhibitor of CDKs. Displays 10 to 20 fold greater potency for p34cdk1, p33cdk2, and p33cdk5 relative to Olomoucine.
      Biological Information
      Primary Targetp34cdk1/cyclin B
      Primary Target IC<sub>50</sub>650 nM, 700 nM, 700 nM, 200 nM, against p34cdk1/cyclin B, p33cdk2/cyclin A, p33cdk2/cyclin E, p33cdk5/p35, respectively
      Purity≥95% by HPLC
      Physicochemical Information
      Cell permeableN
      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). DMSO stock solutions are stable for at least 6 months at -20°C.
      Packaging Information
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Catalogue Number GTIN
      557360-5MG 07790788051495

      Documentation

      Roscovitine - CAS 186692-46-6 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      Roscovitine - CAS 186692-46-6 - Calbiochem Certificates of Analysis

      TitleLot Number
      557360

      References

      Reference overview
      De Azevedo, W.F., et al. 1997. Eur. J. Biochem. 243, 518.
      Meijer, L., et al. 1997. Eur. J. Biochem. 243, 527.
      Meijer, L., et al. 1996. Trends Cell Biol. 6, 393.
      Rudolph, B., et al. 1996. EMBO J. 15, 3053.

      Citations

      Title
    • Linsheng Zhang, et al. (2008) Cyclin-dependent kinase phosphorylation of RUNX1/AML1 on 3 sites increases transactivation potency and stimulates cell proliferation. Blood 111, 1193-1200.
    • Marc Payton, et al. (2006) Discovery and Evaluation of Dual CDK1 and CDK2 Inhibitors. Cancer Research 66, 4299-4308.
    • Meng Qiao, et al. (2006) Cell cycle-dependent phosphorylation of the RUNX2 transcription factor by cdc2 regulates endothelial cell proliferation. Journal of Biological Chemistry 281, 7118-7128.
    • Marie Futter, et al. (2005) Phosphorylation of spinophilin by ERK and cyclin-dependent PK 5 (Cdk5). Procedings of the National Academy of Science 102, 3489-3494.
    • Ping Han, et al. (2005) Suppression of Cyclin-Dependent Kinase 5 Activation by Amyloid Precursor Protein: A Novel Excitoprotective Mechanism Involving Modulation of Tau Phosphorylation. Journal of Neuroscience 25, 11542-11552.
    • Oscar M. Tirado, Silvia Mateo-Lozano and Vicente Notario. (2005) Roscovitine is an effective inducer of apoptosis of Ewing's sarcoma family of tumor cells in vitro and in vivo. Cancer Research 65, 9320-9327.
      		•
      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.

      Revision05-October-2010 JSW
      Synonyms2-(R)-(1-Ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine, Cdk7 Inhibitor I
      DescriptionA potent, reversible, and selective inhibitor of cyclin-dependent kinases (cdks). Exhibits greater inhibitory potency compared to olomoucine (Cat. No. 495620). Inhibits p34 cdc2/cyclin B (IC50 = 0.65 µM), p33 cdk2/cyclin A (IC50 = 0.70 µM), p33 cdk2/cyclin E (IC50 = 0.70 µM), and p33 cdk5/p35 (IC50 = 0.20 µM) by competing for the ATP binding domain of these kinases. Exhibits very low sensitivity towards related kinases, such as erk1 and erk2 (IC50 = 34 µM and 14 µM, respectively). Roscovitine does not significantly affect the activity of other protein kinases even at 100 µM and compared to olomoucine, roscovitine displays increased anti-mitotic activity at the G1/S and G2/M phases of the cell cycle.
      FormWhite to off-white solid
      CAS number186692-46-6
      Chemical formulaC₁₉H₂₆N₆O
      Structure formulaStructure formula
      Purity≥95% by HPLC
      SolubilityDMSO (10 mg/ml)
      Storage -20°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for at least 6 months at -20°C.
      Toxicity Standard Handling
      ReferencesDe Azevedo, W.F., et al. 1997. Eur. J. Biochem. 243, 518.
      Meijer, L., et al. 1997. Eur. J. Biochem. 243, 527.
      Meijer, L., et al. 1996. Trends Cell Biol. 6, 393.
      Rudolph, B., et al. 1996. EMBO J. 15, 3053.
      Citation
    • Linsheng Zhang, et al. (2008) Cyclin-dependent kinase phosphorylation of RUNX1/AML1 on 3 sites increases transactivation potency and stimulates cell proliferation. Blood 111, 1193-1200.
    • Marc Payton, et al. (2006) Discovery and Evaluation of Dual CDK1 and CDK2 Inhibitors. Cancer Research 66, 4299-4308.
    • Meng Qiao, et al. (2006) Cell cycle-dependent phosphorylation of the RUNX2 transcription factor by cdc2 regulates endothelial cell proliferation. Journal of Biological Chemistry 281, 7118-7128.
    • Marie Futter, et al. (2005) Phosphorylation of spinophilin by ERK and cyclin-dependent PK 5 (Cdk5). Procedings of the National Academy of Science 102, 3489-3494.
    • Ping Han, et al. (2005) Suppression of Cyclin-Dependent Kinase 5 Activation by Amyloid Precursor Protein: A Novel Excitoprotective Mechanism Involving Modulation of Tau Phosphorylation. Journal of Neuroscience 25, 11542-11552.
    • Oscar M. Tirado, Silvia Mateo-Lozano and Vicente Notario. (2005) Roscovitine is an effective inducer of apoptosis of Ewing's sarcoma family of tumor cells in vitro and in vivo. Cancer Research 65, 9320-9327.
      		•