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Roscovitine

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Roscovitine Basic information

Product Name:
Roscovitine
Synonyms:
  • Seliciclib
  • 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
  • (2R)-2-[[6-(benzylamino)-9-propan-2-yl-purin-2-yl]amino]butan-1-ol
  • 2-(R)-(1-ETHYL-2-HYDROXYETHYLAMINO)-6-BENZYLAMINO-9-ISOPROPYLPURINE
  • 2-(1-ETHYL-2-HYDROXYETHYLAMINO)-6-BENZYLAMINO-9-ISOPROPYLPURINE
  • 6-BENZYLAMINO-2-(R)-[(1-ETHYL)-2-HYDROXYETHYLAMINO]-9-ISOPROPYLPURINE
  • ROSCOVITINE
  • (R)-ROSCOVITINE
CAS:
186692-46-6
MF:
C19H26N6O
MW:
354.45
Product Categories:
  • Inhibitors
  • Apis
  • API intermediates
Mol File:
186692-46-6.mol
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Roscovitine Chemical Properties

Melting point:
106~107℃
Boiling point:
577.5±60.0 °C(Predicted)
Density 
1.3
storage temp. 
-20°C
solubility 
Soluble in DMSO (up to 10 mg/ml, with warming) or in Ethanol (up to 10 mg/ml).
pka
14.56±0.10(Predicted)
form 
White to off-white solid
color 
White
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey
BTIHMVBBUGXLCJ-OAHLLOKOSA-N
CAS DataBase Reference
186692-46-6(CAS DataBase Reference)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
29335990

MSDS

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Roscovitine Usage And Synthesis

Description

Roscovitine (186692-46-6) is a potent and selective inhibitor of cyclin-dependent kinases displaying higher potency and selectivity compared to olomoucine. ?p34 cdc2 IC50 = 0.2 μM.? Also inhibits p33cdk2 and p33cdk5.1? Anti-angiogenic.2 Prevents PPARg S273 phosphorylation, promoting browning of white adipose tissue.3 Enhances peripheral nerve regrowth.4

Uses

Roscovitine is a potent and selective inhibitor of cyclin-dependent kinases (CDKs). Roscovitine has been found to produce apoptosis in treated cancerous cells of non-small cell lung cancer (NSCLC) and other cancers. Studies show that Roscovitine displays increased anti-mitotic activity at the G1/S and G2/M phases of the cell cycle. Roscovitine maybe useful in the treatment of non-small cell lung cancer (NSCLC), leukemia, HIV infection, herpes simplex infection, and the mechanisms of chronic inflammation disorders.

Definition

ChEBI: 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.

General Description

A potent, reversible, and selective inhibitor of cyclin-dependent kinases (Cdks) that exhibits about ten-fold greater efficacy towards p34cdk1 and p33cdk2 and twenty-fold greater efficacy towards p33cdk5 relative to Olomoucine (Cat. No. 495620). Inhibits p34cdk1/cyclin B (IC50 = 650 nM), p33cdk2/cyclin A (IC50 = 700 nM), p33cdk2/cyclin E (IC50 = 700 nM), and p33cdk5/p35 (IC50 = 200 nM) by competing for the ATP binding domain of the kinases. Exhibits reduced sensitivity towards related kinases including ERK1 and ERK2 (IC50 = 34 μM and 14 μM, respectively). Roscovitine does not significantly affect the activity of other protein kinases even at 100 μM, including p34cdk4/cyclin D1 and p40cdk6/cyclin D2. Compared to olomoucine, roscovitine displays increased anti-mitotic activity at the G1/S and G2/M phases of the cell cycle. A 50 mM (5 mg/282 μl) solution of Roscovitine (Cat. No. 557364) in DMSO is also available.

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.

Anticancer Research

Roscovitine a derivative of olomoucine which is isolated from Raphanus sativus isunder clinical trials (Shoeb 2006).

storage

Store at -20°C

References

1) Meijer et al. (1997), Biochemical and cellular effects of roscovitine, a potent and selective inhibitor of the cyclin-dependent kinases cdc2, cdk2 and cdk5 ; Eur. J. Biochem., 243 527 2) Liebl et al. (2011), Anti-angiogenic effects of purine inhibitors of cyclin dependent kinases; Angiogenesis, 14 281 3) Wang et al. (2016) Browning of White Adipose Tissue with Roscovitine Induces a Distinct Population of UCP1+ Adipocytes; Cell Metab. 24 835 4) Law et al. (2016) Enhancement of Peripheral Nerve Regrowth by the Purine Nucleoside Analog and Cell Cycle Inhibitor, Roscovitine; Front. Cell. Neurosci. 10 238

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