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557360 | Roscovitine - CAS 186692-46-6 - Calbiochem

557360
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₉H₂₆N₆O 186692-46-6

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      557360-1MG
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          Glass bottle 1 mg
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          557360-5MG
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              Glass bottle 5 mg
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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 Image
              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

              Documentation

              SDS

              Title

              Safety Data Sheet (SDS) 

              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 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.