S3939
Staurosporine aglycone
≥95%
Synonym(s):
K-252c
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About This Item
Empirical Formula (Hill Notation):
C20H13N3O
CAS Number:
Molecular Weight:
311.34
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
assay
≥95%
form
crystalline powder
solubility
DMSO: soluble
storage temp.
−20°C
SMILES string
O=C1NCc2c1c3c4ccccc4[nH]c3c5[nH]c6ccccc6c25
InChI
1S/C20H13N3O/c24-20-17-12(9-21-20)15-10-5-1-3-7-13(10)22-18(15)19-16(17)11-6-2-4-8-14(11)23-19/h1-8,22-23H,9H2,(H,21,24)
InChI key
MEXUTNIFSHFQRG-UHFFFAOYSA-N
Gene Information
human ... CDK2(1017)
Application
RGC-5 cells were treated with Staurosporine aglycone to study the effect of staurosporine analogs on the process of neuronal differentiation.
Biochem/physiol Actions
Staurosporine is a microbial alkaloid that inhibits protein kinase C (PKC) but lacks selectivity and may inhibit other protein kinases. Substitution of one of the indole nitrogen atoms by non-glycosidic indolocarbazoles lacking aminoalkyl side chain results in Staurosporine aglycone with increased selectivity for PKC. Staurosporine aglycone inhibits the autophosphorylation of c-Met and activation of MAPK and Akt in cancer cells.
K-252c is a PKC inhibitor active at submicromolar concentrations.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Benedetta Peruzzi et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 12(12), 3657-3660 (2006-06-17)
On binding to the cell surface receptor tyrosine kinase (TK) known as c-Met, hepatocyte growth factor (HGF) stimulates mitogenesis, motogenesis, and morphogenesis in a wide range of cellular targets including, epithelial and endothelial cells, hematopoietic cells, neurons, melanocytes, and hepatocytes.
Non-glycosidic/non-aminoalkyl-substituted indolocarbazoles as inhibitors of protein kinase C
Kleinschroth J et al
Bioorganic & Medicinal Chemistry Letters, 3, 1959-1964 (1993)
Midori A Arai et al.
Bioorganic & medicinal chemistry letters, 19(19), 5778-5781 (2009-09-01)
In the present study, we developed a high-throughput screening system for small molecule-inhibitors of the basic helix-loop-helix (bHLH) transcriptional repressor factor Hes1. Successful dimerization of Hes1 immobilized on a microplate and fluorophore (Cy3)-labelled Hes1 was confirmed. Using this system, several
Alex F Thompson et al.
Neurochemistry international, 56(4), 554-560 (2010-01-02)
RGC-5 cells are transformed cells that express several surface markers characteristic of neuronal precursor cells, but resemble glial cells morphologically and divide in culture. When treated with the apoptosis-inducing agent staurosporine, RGC-5 cells assume a neuronal morphology, extend neurites, stop
Robert L Hudkins et al.
Journal of medicinal chemistry, 50(3), 433-441 (2007-02-03)
Structural modification of the indolecarbazole natural product (+)K-252a identified structural requirements for MLK activity and a novel series of potent fused pyrrolocarbazole MLK1/3 inhibitors. The SAR revealed that the lactam regiochemistry, the shape of the heterocycle, and aryl rings B
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