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ProductsBack/(R)-Roscovitine [186692-46-6]
Chemical Structure
Chemical Structure
Chemical Structure

(R)-Roscovitine [186692-46-6]

Research Use Only
AG-CR1-0006
AdipoGen Life Sciences
CAS Number186692-46-6
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight354.5
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    (R)-Roscovitine [186692-46-6]
  • Delivery Days Customer
    10
  • CAS Number
    186692-46-6
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Molecular Formula
    C19H26N6O
  • Molecular Weight
    354.5
  • Scientific Description
    Chemical. CAS: 186692-46-6. Formula: C19H26N6O. MW: 354.5. Potent and selective inhibitor of CDKs. More potent than olomoucine. Inhibits CDK1/cyclin B kinase (IC50 = 450 nM), CDK2 (IC50 = 700 nM) and CDK5/p35 (IC50 = 160 nM). Inhibits M phase promoting factor (MPF) kinase activity. Arrests human fibroblasts in G1 phase. Antitumor compound. Activates the mitogen-activated protein kinase pathway. Targets both the p53 and NF-kappaB pathways[10]. Has effects on calcium channel gating. Prevents DNA damage-induced cyclin A1 upregulation. Apoptosis inducer. As CYC202 in phase I clinical trials. Reviews. - Potent and selective inhibitor of CDKs [1, 2, 4, 16]. More potent than olomoucine [3]. Inhibits CDK1/cyclin B kinase (IC50 = 450 nM) [2], CDK2 (IC50 = 700 nM) [4] and CDK5/p35 (IC50 = 160 nM) [4,5]. Inhibits M phase promoting factor (MPF) kinase activity [2]. Arrests human fibroblasts in G1 phase [6]. Antitumor compound [8]. Activates the mitogen-activated protein kinase pathway [9]. Targets both the p53 and NF-kappaB pathways[10]. Has effects on calcium channel gating [12, 17, 18]. Prevents DNA damage-induced cyclin A1 upregulation [13]. Apoptosis inducer [11, 15, 20]. As CYC202 in phase I clinical trials [14]. Reviews [3, 7, 19].
  • SMILES
    CC[C@H](CO)NC1=NC2=C(N=CN2C(C)C)C(NCC2=CC=CC=C2)=N1
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • Activation of cyclin-dependent kinases by Myc mediates induction of cyclin A, but not apoptosis: B. Rudolph, et al.; EMBO J. 15, 3065 (1996)
  • Biochemical and cellular effects of roscovitine, a potent and selective inhibitor of the cyclin-dependent kinases cdc2, cdk2 and cdk5: L. Meijer, et al.; Eur. J. Biochem. 243, 527 (1997)
  • Chemical inhibitors of cyclin-dependent kinases: L. Meijer and S.H. Kim; Meth. Enzymol. 283, 113 (1997)
  • Cytokinin-derived cyclin-dependent kinase inhibitors: synthesis and cdc2 inhibitory activity of olomoucine and related compounds: L. Havlicek, et al.; J. Med. Chem. 40, 408 (1997)
  • Direct in vivo inhibition of the nuclear cell cycle cascade in experimental mesangial proliferative glomerulonephritis with Roscovitine, a novel cyclin-dependent kinase antagonist: J.W. Pippin, et al.; J. Clin. Invest. 100, 2512 (1997)
  • The cyclin-dependent kinase inhibitors olomoucine and roscovitine arrest human fibroblasts in G1 phase by specific inhibition of CDK2 kinase activity: F. Alessi, et al.; Exp. Cell Res. 245, 8 (1998)
  • The specificities of protein kinase inhibitors: an update: J. Bain, et al.; Biochem. J. 371, 199 (2003)
  • In vitro and in vivo antitumor properties of the cyclin dependent kinase inhibitor CYC202 (R-roscovitine): S.J. McClue, et al.; Int. J. Cancer 102, 463 (2002)
  • The Cyclin-dependent kinase inhibitor CYC202 (R-roscovitine) inhibits retinoblastoma protein phosphorylation, causes loss of Cyclin D1, and activates the mitogen-activated protein kinase pathway: S.R. Whittaker, et al.; Cancer Res. 64, 262 (2004)
  • R-Roscovitine simultaneously targets both the p53 and NF-kappaB pathways and causes potentiation of apoptosis: implications in cancer therapy: A. Dey, et al.; Cell Death Differ. 15, 263 (2008)