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R7772

Sigma-Aldrich

Roscovitine

≥98% (TLC)

Synonym(s):

2-(R)-[[9-(1-Methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-butanol, 6-(Benzylamino)-2(R)-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine

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About This Item

Empirical Formula (Hill Notation):
C19H26N6O
CAS Number:
186692-46-6
Molecular Weight:
354.45
MDL number:
MFCD02266401
UNSPSC Code:
12352200
PubChem Substance ID:
24278682
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (TLC)

form

powder

mp

106-107 °C

solubility

chloroform: 50 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

CC[C@H](CO)Nc1nc(NCc2ccccc2)c3ncn(C(C)C)c3n1

InChI

1S/C19H26N6O/c1-4-15(11-26)22-19-23-17(20-10-14-8-6-5-7-9-14)16-18(24-19)25(12-21-16)13(2)3/h5-9,12-13,15,26H,4,10-11H2,1-3H3,(H2,20,22,23,24)/t15-/m1/s1

InChI key

BTIHMVBBUGXLCJ-OAHLLOKOSA-N

Gene Information

human ... CDK1(983) , CDK2(1017) , CDK5(1020) , CDK7(1022) , CDK9(1025) , CDKN1A(1026) , CDKN1B(1027) , CDKN1C(1028) , CDKN2A(1029) , CDKN2B(1030) , CDKN2C(1031) , CDKN2D(1032) , CDKN3(1033)
mouse ... CDK1(12534)
rat ... CDK1(54237)

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Application

Roscovitine has been used:
  • an inhibitor of p34cdc2/cyclin B kinase to preculture porcine oocytes
  • as a supplement in TCM199 medium for in vitro prematuration of cumulus-oocyte complexes (COCs) of adult goats
  • in astrocyte conditioned media as an inhibitor of cyclin-dependent kinase 5 (CDK5)
  • as a CDK2 inhibitor in culture media to treat hESCs

Biochem/physiol Actions

Roscovitine is a purine derived inhibitor. It stimulates apoptosis in cancer cells. It has inhibitory action on mitogen activated protein kinase (MAPK) and M-phase promoting factor (MPF) kinase activity. Roscovitine is known to arrest meiosis and thus, prevent embryonic development.
Roscovitine is a potent, selective inhibitor of cyclin-dependent kinases.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the CDKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

Sold under license from CNRS

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Birth of piglets after transferring of in vitro-produced embryos pre-matured with R-roscovitine
Coy P, et al.
Reproduction (Cambridge, England), 129(6), 747-755 (2005)
Advances in Putrescine Research and Application, 4-4 (2013)
Qian Liang et al.
Scientific reports, 3, 2932-2932 (2013-10-15)
Epithelial-mesenchymal transition is a change of cellular plasticity critical for embryonic development and tumor metastasis. CDK5 is a proline-directed serine/threonine kinase playing important roles in cancer progression. Here we show that CDK5 is commonly overexpressed and significantly correlated with several
Eva Maria Putz et al.
Cell reports, 4(3), 437-444 (2013-08-13)
The transcription factor STAT1 is important in natural killer (NK) cells, which provide immediate defense against tumor and virally infected cells. We show that mutation of a single phosphorylation site (Stat1-S727A) enhances NK cell cytotoxicity against a range of tumor
Bich Na Shin et al.
Scientific reports, 9(1), 13032-13032 (2019-09-12)
Abnormal activation of cyclin-dependent kinase 5 (Cdk5) is associated with pathophysiological conditions. Ischemic preconditioning (IPC) can provide neuroprotective effects against subsequent lethal ischemic insult. The objective of this study was to determine how Cdk5 and related molecules could affect neuroprotection
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