Aloisine AAn inhibitor of CDK1, CDK2, CDK5, GSK-3 alpha, and JNK

Aloisine A (CAS 496864-16-5)

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Synonym: RP107; 7-n-Butyl-6-(4-hydroxyphenyl)[5H]pyrrolo[2,3-b]pyrazine
Application: An inhibitor of CDK1, CDK2, CDK5, GSK-3 alpha, and JNK
CAS Number: 496864-16-5
Purity: ≥95%
Molecular Weight: 267.33
Molecular Formula: C16H17N3O
* Refer to Certificate of Analysis for lot specific data (including water content).
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Aloisine A is a cell permeable, potent, selective, reversible, and ATP-competitive inhibitor of Cdc2 (CDK1)/cyclin B (IC50 = 150nM), Cdk2/cyclin A (IC50 = 120nM), Cdk2/cyclin E (IC50 = 400nM), Cdk5/p25 (IC50 = 200nM), Cdk5/p35 (IC50 = 160nM), and GSK-3α (IC50 = 500nM). Aloisine A also inhibits GSK-3β (IC50 = 650nM) and JNK (c-Jun N-terminal kinase) (IC50~3-10μM). Aloisine A is a poor inhibitor of CK1, CK2, Cdk4/cyclin D1, MAPKK, PKA, PKG, PKCs and c-raf (IC50 ≥ 100μM). Aloisine A blocks the cell cycle in both G1 and G2 phase. Aloisine A is an activator of CFTR.


References

1. Mettey, Yvette., et al., 2003. Aloisines, a new family of CDK/GSK-3 inhibitors. SAR study, crystal structure in complex with CDK2, enzyme selectivity, and cellular effects. Journal of medicinal chemistry. 46(2): 222-36. PMID: 12519061
2. Noel, Sabrina., et al., 2006. Discovery of pyrrolo[2,3-b]pyrazines derivatives as submicromolar affinity activators of wild type, G551D, and F508del cystic fibrosis transmembrane conductance regulator chloride channels. The Journal of pharmacology and experimental therapeutics. 319(1): 349-59. PMID: 16829626
3. Corbel, Caroline., et al., 2009. Identification of potential cellular targets of aloisine A by affinity chromatography. Bioorganic & medicinal chemistry. 17(15): 5572-82. PMID: 19596197

Physical State :
Solid
Solubility :
Soluble in DMSO (>10 mg/ml), and methanol. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
281-283° C
Boiling Point :
459.64° C (Predicted)
Density :
1.23 g/cm3 (Predicted)
Refractive Index :
n20D 1.66 (Predicted)
IC50 :
Cdk1/cyclin B: IC50 = 150 nM; Cdk2/cyclin A: IC50 = 120 nM; Cdk2/cyclin E: IC50 = 400 nM; Cdk5/p25: IC50 = 200 nM; GSK-3a: IC50 = 500 nM; GSK-3Β: IC50 = 650 nM; JNK: IC50 = ~3-10 µM; CDK5/p35: IC50 = 160 nM; c-raf: IC50 = ≥100 µM; CK1: IC50 = ≥100 µM; CK2: IC50 = ≥100 µM; MAPKK: IC50 = ≥100 µM; PKA: IC50 = ≥100 µM; PKG: IC50 = ≥100 µM; PKCs: IC50 = ≥100 µM; CFTR-dependent iodide efflux: EC5050 = 150 nM (wtCFTR-CHO cells); CFTR-dependent iodide efflux: EC5050 = 140 nM (Calu-3 cells); CFTR-dependent iodide efflux: EC5050 = 111 nM (F508del-CFTR-CF15 cells); undifferentiated human teratocarcinoma cells NT2: IC50 = 7 µM; differentiated postmitotic neurons hNT: IC50 = 10.5 µM
pK Values :
pKa: 9.67, pKb: 3.47
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
5326843
MDL Number :
MFCD04973541
SMILES :
CCCCC1=C(NC2=C1N=CC=N2)C1=CC=C(O)C=C1

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Certificate of Analysis

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