CHIR-99021
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Grundinformationen
- CAS
252917-06-9- Standard-SMILES
Cc1cnc(-c2cnc(NCCNc3ccc(C#N)cn3)nc2-c2ccc(Cl)cc2Cl)[nH]1- InChIKey
AQGNHMOJWBZFQQ-UHFFFAOYSA-N- Summenformel
- C22H18Cl2N8
- Durchschnittliche Molmasse
- 465,348 g/mol
- Monoisotopische Masse
- 464,10314794
Namen und Bezeichner
- Bevorzugter Name
- CHIR-99021
- IUPAC
- 6-[(2-{[4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl]amino}ethyl)amino]pyridine-3-carbonitrile
- Englischer Name
- CHIR-99021
- Summenformel
- C22H18Cl2N8
- Molmasse
- 465.34
Namen und Synonyme
LaduviglusibCHIR-99021 (CT99021) HClCT990216-((2-((4-(2,4-Dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrileGSK 3IXVCHIR9921CHIR CHIRCHIR73911CHIR-99021CHIR-99012
Datenbank-Bezeichner
- CAS
252917-06-9- PubChem CID
- 9956119
- DTXSID
DTXSID90179931- ChEMBL
CHEMBL412142- ChEBI
CHEBI:91091- UNII
- 234CMT4GK4
- EC Number
- 809-015-4
- Nikkaji
- J2.462.849C
Eigenschaften
Physikochemische Eigenschaften
- Siedepunkt
- 784.1 · 784.1±70.0 °C(Predicted)
- Dichte
- 1.48 · 1.48
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 2 mg/mL, · DMSO: soluble2mg/mL, clear (warmed)
- pka
- 11.92 · 11.92±0.10(Predicted)
- Aggregatzustand
- powder
- Farbe
- white to light brown
- Stabilität
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
- InChIKey
- AQGNHMOJWBZFQQ-UHFFFAOYSA-N
- SMILES
- C1=NC(NCCNC2=NC=C(C3NC(C)=CN=3)C(C3=CC=C(Cl)C=C3Cl)=N2)=CC=C1C#N
- CAS Datenbank
- 252917 · 252917-06-9
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29335990
- risk_code
- 25-36/37/38
- hazard_code
- T
- safety_code
- 26-36/37/39-45
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Anwendungen
BeschreibungCHIR99021 is an aminopyrimidine derivative that is an extremely potent glycogen synthase kinase (GSK) 3 inhibitor, inhibiting both GSK3β (IC = 6.7 nM) and GSK3α (IC = 10 nM). GSK3 is a serine/threonine kinase that is a key inhibitor of the WNT pathway; therefore CHIR99021 functions as a WNT activator. It shows little activity against a large panel of kinases including CDK2 and other serine/threonine kinases such as MAPK and PKB (Bain et al.).CHIR99021 promotes self-renewal potential of embryonic stem cells (ESCs) of mice by inhibiting glycogen synthase kinase-3 (GSK-3) activity and potentiates the upregulation of β-catenin and c-Myc functions. CHIR99021 promotes self-renewal of ESCs by modulating transforming growth factor β (TGF-β), Notch and mitogen-activated protein kinases (MAPK) signaling pathways. CHIR99021 is an agonist of wingless/integrated (wnt) signalling, upregulates cyclinA expression and promotes cell proliferation in non-small-cell lung cancer (NSCLC) cell lines.
VerwendenA specific GSK-3 inhibitor of GSK-3β and GSK-3α with IC50s of 5 nM and 10 nM, respectively.
Ergänzende Hinweise
DefinitionChEBI: A member of the class of aminopyrimidines that is 2-aminopyrimidine substituted at positions N2, 5 and 6 by (5-cyanopyridin-2-yl)ethyl, 4-methylimidazol-2-yl and 2,4-dichlorophenyl groups respectively.
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