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Merck
CN

S3939

Sigma-Aldrich

Staurosporine aglycone

≥95%

Synonym(s):

K-252c

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About This Item

Empirical Formula (Hill Notation):
C20H13N3O
CAS Number:
85753-43-1
Molecular Weight:
311.34
MDL number:
MFCD00236435
UNSPSC Code:
12352200
PubChem Substance ID:
24899575

Key Documents

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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

K-252c is a PKC inhibitor active at submicromolar concentrations.
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.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBK7056V
SLBJ2741V
021M15481V
071M1824V
021M1548V

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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
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)
Lawrence J Wilson et al.
Bioorganic & medicinal chemistry letters, 19(12), 3333-3338 (2009-05-12)
The synthesis and biological evaluation of JAK3 based staurosporine compounds is described. The compounds are constructed completely de novo, and a ring closing metathesis strategy is used to assemble the sugar mimetic portion. These analogs show potent JAK3 activity against
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