R7772

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
• 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

Properties

• 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)

Description

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

Safety Information

• 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