Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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)

Looking for similar products? Visit Product Comparison Guide

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

API-1

Sigma-Aldrich

SML1342

API-1

R547 ≥98% (HPLC)

Sigma-Aldrich

SML1254

R547

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
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
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)
View All Related Papers

Related Content

Discover Bioactive Small Molecules for Cell Cycle Research

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service