Roscovitine
Synonym(s):2-(R)-[[9-(1-Methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-butanol;2-(R)-(1-Ethyl-2-hydroxyethylamino)-6-benzylamino-9-isopropylpurine, Cdk7 Inhibitor I;6-(Benzylamino)-2(R)-[[1-(hydroxymethyl)propyl]amino]-9-isopropylpurine;Roscovitine - CAS 186692-46-6 - Calbiochem
- CAS NO.:186692-46-6
- Empirical Formula: C19H26N6O
- Molecular Weight: 354.45
- MDL number: MFCD02266401
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-01 20:20:38
What is Roscovitine?
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
The Uses of Roscovitine
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 c ancer (NSCLC), leukemia, HIV infection, herpes simplex infection, and the mechanisms of chronic inflammation disorders.
The Uses of Roscovitine
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.
What are the applications of Application
Roscovitine is a potent and selective inhibitor of cyclin-dependent kinases. Selective for Cdk1, Cdk2, and Cdk5
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
Properties of Roscovitine
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). |
form | White to off-white solid |
pka | 14.56±0.10(Predicted) |
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. |
CAS DataBase Reference | 186692-46-6(CAS DataBase Reference) |
Safety information for Roscovitine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for Roscovitine
InChIKey | BTIHMVBBUGXLCJ-OAHLLOKOSA-N |
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