Roscovitine
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
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)
Safety Information
- Safety Statements
- 22-24/25
- WGK Germany
- 3
- HS Code
- 29335990
MSDS
- Language:English Provider:SigmaAldrich
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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- Roscovitine
- SELICICLIB
- (S)-ROSCOVITINE
- S-ROSCOVITINE 98% (HPLC),ROSCOVITINE, (S)-ISOMER,(S)-ROSCOVITINE
- RS-ROSCOVITINE 98% (HPLC)
- (R)-ROSCOVITINE, >95%
- ROSCOVITINE, IMMOBILIZED
- OLOMOUCINE II
- ROSCOVITINE, 99+%