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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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      557360-5MGCN
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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
          557360-1MGCN 04055977267983
          557360-5MGCN 07790788051495

          Documentation

          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.
          		•