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R7772

Roscovitine

Name: Roscovitine
Brand: SIGMA

synthetic (organic), ≥98% (TLC), cyclin-dependent kinases inhibitor, powder

Sinónimos:

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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Fórmula empírica (notación de Hill):

C₁₉H₂₆N₆O

Número CAS:

186692-46-6

Peso molecular:

354.45

UNSPSC Code:

12352200

PubChem Substance ID:

24278682

NACRES:

NA.77

MDL number:

MFCD02266401

Assay:

≥98% (TLC)

Form:

powder

Quality level:

200

Servicio técnico

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Propiedades

Nombre del producto

Roscovitine, ≥98% (TLC)

biological source

synthetic (organic)

Quality Level

200

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)

Descripción

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

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Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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)

Down-regulation of cyclin-dependent kinase 5 attenuates p53-dependent apoptosis of hippocampal CA1 pyramidal neurons following transient cerebral ischemia.

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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